Hillary Clinton’s


Cherie Diez | Times
Hillary Clinton at St. Petersburg's Coliseum in June 1996.

Clinton’s connections in the Sunshine State are about
loyalty and longevity — and Bill.

Hillary Clinton’s relationship with Florida, not unlike an enduring but exacting marriage, is long and complex.

Consider her journey from idealistic law student at Yale sticking up for Florida migrant workers to presidential frontrunner chatting up the corporate elite who paid $50,000 a plate to dine with her on Miami Beach’s Star Island.

In July 1970, 22-year-old Hillary Rodham, an intern for a children’s advocacy group in Washington, was sent to monitor Walter Mondale’s Senate committee hearings about terrible working conditions on corporate-owned farms in Florida.

Some Yale classmates with internships at big law firms saw the hearings as proof that agribusinesses needed better PR. But Clinton, who had babysat migrant children in Illinois, had a different take.

“I suggested that the best way to do that would be to improve the treatment of their farm workers,” Clinton wrote in an autobiography. She threw herself into studying how laws affect children.

Fast forward 20 years. Arkansas Gov. Bill Clinton launches a bid for president with his lawyer-wife at his side and they target Florida as key to winning the Democratic nomination. They seek the money and support of sugar baron Alfonso “Alfy” Fanjul, whose family-owned company faced numerous lawsuits alleging mistreatment of Jamaican guest workers cutting cane in South Florida’s muck. No matter. Fanjul becomes co-chairman of the 1992 Clinton campaign.

Getty Images
Sugar magnate Alonso "Alfy" Fanjul of Palm Beach, here at a 1999 White House state dinner for Argentina's president, has been an adviser and major donor to the Clintons since they first started campaigning in Florida in 1991. His brother, José "Pepe" Fanjul, is a major GOP donor who helped Marco Rubio this cycle.

Four years later, an embarrassing political footnote: President Clinton was in the Oval Office with Monica Lewinsky when he had a 22-minute phone call with Fanjul, whose industry enjoyed special protections under Clinton’s NAFTA deal.

Today, most of the cane cutters are gone from the Fanjul fields in South Florida, replaced by machinery. But the Fanjul family remains tight with the Clintons, donating at least $100,000 to the Clinton Foundation. Records show Alfy Fanjul met numerous times privately with Secretary of State Clinton. In August, shortly after the Democratic National Convention, Fanjul, his wife, Raysa, and former Ambassador Paul Cejas and his wife host a $100,000-per-couple dinner at Cejas’ Miami Beach mansion for the Democratic nominee who decries the unfair clout of the rich.

Call the Clinton-Fanjul ties irony, or even hypocrisy. Ultimately, the story of Hillary Clinton and her relationships in Florida is one of longevity.

“It’s not anything new with the Clintons’ calculus,” said Gregory Schell, a Palm Beach County lawyer who has spent decades fighting for farm workers — and suing the Fanjuls. “Everything about them is bottom line and the ends justify the means. They want to win.”

Schell plans to vote for her.

Associated Press, 1992
The Clintons speak outside the Tampa Convention Center on the eve of sweeping "Super Tuesday" states, including Florida, and effectively clinching the Democratic nomination in 1992.

Relationships matter

Every serious presidential candidate develops allegiances to Florida, especially South Florida because it’s a silver mine for votes and a gold mine for campaign checks.

The Clintons’ Sunshine State ties, however, are wider and deeper than any modern presidential nominee not named Bush. Florida is a mega state where relationships still matter in politics, and Bill and Hillary have cultivated friendships, personal bonds and crony connections for decades.

“This couple has been part of our lives for a quarter of a century,” said Miami lawyer Ira Leesfield, who has raised or donated millions of dollars for multiple Clinton campaigns, the presidential library and the foundation. He raised money for Barack Obama, too, but much more for the Clintons, who have kept in touch with him and his wife: “If you have a family member or close friend who needs something, you generally respond more generously when it’s someone you deeply care about and like.”

The state is loaded with men and women who have known Hillary Clinton for years, even say they adore her, though they acknowledge they’re not close to her.

Associated Press, 1997
Hillary Clinton attends "One Voice for Children Day" in Tallahassee in April 1997. Here she greets 4-month-old Sara Heuler and her mother, Victoria Heuler, at an advocacy training session.

“She’s just quite cordial and warm, but Bill is the one who really gathers people around him,” said former Chief Financial Officer Alex Sink, who hosted Hillary Clinton at her home for a fundraising reception in December. Sink has known her since the mid 1980s when she and late husband Bill McBride attended “Renaissance Weekend” retreats of business and political leaders in Hilton Head, S.C. “Honestly, I never felt I could just go up and strike up a conversation with her.”

Floridians who have spent hours with Bill Clinton — in the White House, on golf courses (he’s regularly on the links in Florida), private planes, and in hotel suites — have colorful stories about interacting with a once-in-a-generation politician who can remember every detail of their lives, or become petulant during late night Oh Hell card games.

The more disciplined, more reserved Hillary Clinton, 68, doesn’t play golf. She will drink with friends but doesn’t stay up late gabbing. And she connects with individuals much easier than with crowds.

Chris Korge, a Miami investor, former lobbyist, and one of America’s top Democratic money-raisers, probably knows the woman behind the guarded persona as well as almost any Floridian besides her brother, Coral Gables resident Hugh Rodham.

“Hillary is one of the most misunderstood people I’ve ever met,” Korge said. “She’s funny, she’s clever, she genuinely likes people. She doesn’t have that natural gift that President Clinton does of remembering every minute detail of everybody, but I’ll tell you what — and I’ve said this to his face — she’s even smarter than he is.”

Associated Press, 1994
During the 1994 Summit of the Americas in Miami, the first lady visits with nurse Therese Coyne and 5-year-old Keona Turner at Jackson Memorial Pediatric Mobile Center.

Before Korge and his wife divorced, the former first lady, whose marital problems played out so publicly, would talk to him about the importance of marriage counseling. “She was almost like a big sister, really caring. She would offer advice,” he said.

U.S. Rep. Alcee Hastings, a Delray Beach Democrat, first met Clinton in the 1970s when she worked at the Children’s Defense Fund and he was a juvenile court judge. Decades later he would spend hours with both Clintons at the White House and on Air Force One for two trips to Israel.

She has an easy laugh and genuine interest in and compassion for people that, he said, is more apparent in one-on-one settings than it is with either President Obama or President George W. Bush.

“She’s just regular, is the best way to put it, even though it doesn’t always come across that way to people,” said Hastings, who recently joined Clinton for a meeting with black mothers whose children died in gun violence. “I can tell you there wasn’t a dry eye in the room.”

Associated Press
Trayvon Martin's mother, Sybrina Fulton, introduces Clinton at the Trayvon Martin Foundation’s Circle of Mothers gala in Fort Lauderdale in May.

A package deal

State Rep. Joe Geller, a former Miami-Dade Democratic chairman, for years heard about Bill and Hillary Clinton while attending Young Democrats of America conventions. Delegates from Arkansas boasted about their progressive, Rhodes Scholar governor and his brilliant, idealistic wife.

“That was part of his appeal,” said Geller, an attorney. “He wasn’t another old-fashioned macho governor but a modern guy with a wife involved and just as impressive.”

Courtesy of Nan Rich, 2003
Former state Sen. Nan Rich of Broward County worked with Clinton on the Home Instruction for Parents of Preschool Youngsters program.

Nan Rich’s bond with Clinton goes back to 1985, when an aide to the first lady of Arkansas phoned, asking Rich to come to a conference on early childhood learning in Little Rock. Clinton had recently been in Miami representing her husband at a Southern Governors’ Conference and clipped out a Miami Herald article about a preschool program Rich and the National Council of Jewish Women had just started in Miami-Dade.

Clinton wanted to bring it to Arkansas, which at the time did not even have mandatory kindergarten.

“She was so much fun and so gracious and really excited about getting that program started,” recounted Rich, a former state senator.

Jorge Perez, a billionaire Miami developer and fundraiser, first met Hillary Clinton when he flew to Little Rock to meet with the governor. They talked about affordable housing, health care, Gabriel García Marquez’s One Hundred Years of Solitude, and then Hillary Clinton joined them spontaneously and the three of them had lunch. “I was totally taken,” said Perez. He described her as smart — an operative and a surrogate.

Arthenia Joyner, veteran civil rights activist and state senator from Tampa, met Bill Clinton when she led the National Bar Association for black lawyers. Her bond with Hillary Clinton began at a 1992 rally in downtown Tampa, when Clinton had to kill time before her husband’s plane arrived.

“She spoke for 20 minutes. Did not look at a single note,” Joyner said. “It was so impressive to me as a woman to see this governor with a woman whose abilities, and intellect, are equal or better to his.”

Times files, 2008
State Sen. Arthenia Joyner of Tampa, one of the Clintons' closest friends in Florida, cheers for Hillary at a debate watch party in January 2008.

Miami Beach businessman Philip Levine came to know President Clinton during Al Gore’s 2000 campaign and became one of his closest friends in Florida. Levine has traveled the world with President Clinton, including traveling home from Australia with the former president by military cargo jet because America was under attack on 9/11.

Then-Sen. Clinton met them at the airport at 3 a.m., and Levine slept on their couch in Chappaqua, N.Y.

Levine is among those loyalists who say the Clintons remain incredibly close, even through years of doubts about their marriage. “I know whenever I’m with President Clinton, they’re talking constantly through the day. She’s calling him, and he’s calling her,” Levine said. “I don’t get into someone else’s personal relationships, but I know what I’ve observed.”

Associated Press, 1998
The Clintons watch the space shuttle Discovery rise off the launch pad at Kennedy Space Center in Cape Canaveral in October 1998.

Political instincts

Few Democrats 25 years ago saw much chance of beating President George H.W. Bush in the state that had gone Democratic in just one presidential election since 1964 (Jimmy Carter in 1976).

But the Clintons instinctively understood Florida’s multiple personalities — rural, urban, suburban, southern, northern, midwestern.

“In a state that sometimes seems as complicated as a U.N. meeting, they had comfort levels with all the various components of Florida that other candidates would spend years trying to develop,” said longtime Clinton adviser Craig Smith, noting that they lived in Arkansas, were educated in the northeast and she grew up in the Chicago suburbs.

Focused on the Democratic primary, Clinton’s team set its sights on a Florida Democratic Convention in December 1991 that included a nonbinding straw poll for more than 2,300 delegates. The campaign saw a big opportunity to stand out in a field that included Sens. Tom Harkin of Iowa, Bob Kerrey of Nebraska, former Massachusetts Sen. Paul Tsongas, Virginia Gov. Doug Wilder, former California Gov. Jerry Brown and, potentially, New York Gov. Mario Cuomo.

Times files, 1996
Hillary Clinton and Florida Gov. Lawton Chiles visit the Florida delegation breakfast at the Democratic National Convention in 1996.

Few voters knew anything about Bill Clinton back then, but he had established important political contacts throughout Florida.

In 1985, Clinton and then-Sen. Lawton Chiles helped establish the Democratic Leadership Council, which aimed to move the party toward the center after three presidential campaign losses. Sen. Bob Graham and Clinton were mutual admirers from when both were progressive southern governors.

“Remember, Bill Clinton was head of the National Governors Association, so he was going to Florida and meeting people for years before he ran for president,” said Virginia Gov. Terry McAuliffe, himself a top money-raiser for both Clintons with deep Florida family ties.

Chiles said he had too many friends in the race to lead Clinton’s Florida campaign, but Lt. Gov. Buddy MacKay was happy to take the helm.

In November 1991, Clinton and Craig Smith flew into Tallahassee to meet with MacKay and Democratic state legislators. MacKay sent the state trooper assigned to his detail, 25-year-old Kendrick Meek, to pick up the governor. Meek kept quiet as he overheard the two men mentioning U.S. Rep. Carrie Meek of Miami as one of the influential Florida Democrats they wanted to court. They didn’t know that’s his mother.

Clinton asked to stop at the Suwannee Swifty on the way to the state Capitol to buy some deodorant. The governor unbuttoned his shirt and rolled it on in the parking lot, as Meek watched for potential security threats.

Associated Press, 2007
Then-Rep. Kendrick Meek and his mom, former congresswoman Carrie Meek, join Clinton in the Liberty City area of Miami for her first presidential campaign appearance in Florida in February 2007.

The straw poll

The Clintons represented a break from the liberal Democratic Party establishment, a modern, pro-business, socially conscious couple. Bill was the candidate, but Hillary was at his side or never far behind.

Together, the Clintons could cover a lot of ground. Hillary Clinton took campaign swings through Florida that fall, meeting with prominent political players.

Former Miami-Dade Democratic Party Chairman Geller remembers driving to the Broward School Board building to pick her up. She spotted the golf clubs in the trunk of his Mercedes. Oh, you have to meet my brothers in Miami, Tony and Hugh, who love golf, she gushed.

The Democratic convention weekend kicked off in mid December, and the Clinton campaign owned the event from start to finish. They commandeered the hotel phone system so that a recorded message from Gov. Clinton greeted every delegate. While Harkin, Kerrey and Tsongas worked the crowd, none could match the relentless two-person charm offensive from Bill and Hillary.

Associated Press, 1991
Arkansas Gov. Bill Clinton speaks at the Florida Democratic Convention in December 1991 before winning a straw poll that helped make him a frontrunner for the Democratic nomination.

He would hit the African-American caucus, while she met with the disability caucus.

Other times they tag-teamed undecided delegates.

“I would bring them to the hallway outside the connecting suite and give them a talking to, including the basic talking points as to why we thought Gov. Clinton was by far the best choice for a nominee. Then I would take them into one of the rooms, and there was Hillary,” Geller recounted. “She would turn on the charm and give them the full treatment, all the policy reasons and everything else. Then she’d pass them through the connecting door to the governor, as soon as he’d finished with who he was in with, and he would close the deal. ... We had almost an assembly line going.”

At the final dinner, delegates found fortune cookies at their plates that read, “There’s a Clinton in your future.”

“Nobody had ever seen anything like this before. The Clintons just flat out-organized everybody else,” said Tampa Mayor Bob Buckhorn, who was part of their organizing team that weekend.”

Clinton won the straw poll with 54 percent support, blowing out the better-known Harkin, who drew 31 percent.

“It really started here in Florida,” declared Clinton when he returned to Tampa a month later as the Democratic frontrunner. “Until the Florida straw poll, no one outside of my own state had ever voted for me for anything.”

Saving the campaign

Particularly novel for a Democrat at the time was Clinton’s aggressive outreach to Miami-Dade’s overwhelmingly Republican Cuban-American community. A riot by hundreds of refugees at a military training facility in Arkansas helped cost Clinton re-election as governor in 1980, so he was attuned to Cuba policy issues.

Hard-line anti-Castro sentiments were common among DLC Democrats, and Hillary Clinton’s sister-in-law — Hugh’s wife, Miami attorney Maria Arias — was a native of Cuba. She and several prominent Cuban-American businessmen, including developer Jorge Perez, investor Paul Cejas, Florida Democratic Party Chairman Simon Ferro and Fanjul, the sugar company magnate, remained close advisers to Clinton for years.

Associated Press, 1992
Few Democrats 25 years ago saw much chance of beating President George H.W. Bush, but Bill Clinton did. The Democratic hopeful greets a crowd at a town hall meeting at Florida A&M University during the 1992 campaign.

Perez said he opposed the embargo back then, but urged Clinton to back it.

“I told Clinton to be hard-line on Cuba. I told him he should be more hard-line than the Republicans, even if I hated that, because that’s how you win the hearts and minds of Cuban-Americans and take Florida,” said Perez, who later helped host a reception for Clinton at Victor’s Cafe in Miami that attracted Jorge Mas Canosa, founder of the Cuban-American National Foundation.

“That group actually saved the Clinton campaign,” said Mitchell Berger, a Fort Lauderdale lawyer and a prolific Democratic fundraiser. He recounts how Clinton supporters and donors across the country thought Clinton’s campaign was sunk after Gennifer Flowers emerged in early 1992 saying she had a long-term affair with the governor.

“Right after that first woman story came out, they flew to Little Rock and brought the campaign like $100,000 — which was real money back then. Jorge Perez led that effort.”

Tampa Mayor Sandy Freedman remembers watching the 60 Minutes interview on Jan. 26, 1992, with the Clintons answering to the Flowers controversy. She had not yet met Hillary Clinton but was excited to see a modern feminist, a smart and accomplished leader at Clinton’s side. “It was so refreshing, almost kind of like a validation,” Freedman said. “It was like a sister.”

Gov. Clinton recovered with a second-place “comeback kid” finish in New Hampshire and went on to win the nomination. The campaign invested little money in Florida during the general election, seeing it as a long shot, but Hillary Clinton made at least half a dozen campaign trips to the state that year.

Bill Clinton lost Florida by less than 2 percentage points.

Associated Press, 1992
Hillary Clinton greets supporters after a speech at the International Ladies' Garment Workers Union convention in Miami Beach.

First-state treatment

The Florida flirtation of 1992 turned into a full-fledged relationship after the Clintons moved into the White House. More than merely being prescient about the state’s political potential, the Clintons recognized Florida as a top-tier, top-priority state.

Circumstances ensured the White House’s immediate attention.

A flood of Haitian boat people headed to South Florida prompted the president to abandon a campaign pledge to give Haitians asylum. Post-Hurricane Andrew rebuilding remained a top priority, and Clinton vowed to unclog bureaucratic logjams on funding and released $76 million for flattened Homestead Air Force Base.

Associated Press, 1993
The Clintons arrive in Miami for Labor Day weekend in 1993.

Top appointments included Janet Reno of Miami as attorney general (recommended by Hugh Rodham, who worked with the state attorney establishing a drug court in Miami-Dade) and Florida Secretary of Environmental Regulation Carol Browner as EPA administrator. Some top Cuban-American supporters received ambassadorships: Cejas to Belgium and Ferro to Panama.

Both Clintons visited the state regularly for official and political business, and Floridians including Geller, Freedman, Marjory Stoneman Douglas, Democratic fundraiser Dick Batchelor of Orlando, Gov. Chiles, fundraisers Ira and Cynthia Leesfield, and state Sen. Daryl Jones slept in the White House’s Lincoln Bedroom. Or tried to.

“I didn’t sleep at all. They had an electric blanket on the bed in July, and I had never used one and didn’t know how to turn the darn thing off,” Freedman recounted with a chuckle. “I pushed it off the bed, but the bed was so hot I couldn’t sleep. I did get to read the Gettysburg Address about 20 times, since it was sitting on Lincoln’s desk.”

The Clintons’ first visit to Florida that term was to check on Hurricane Andrew recovery efforts. As they walked through the Fontainebleau Miami Beach, their entourage included Trooper Kendrick Meek.

President Clinton “turned around as we’re all walking through the hallway and says, ‘Kendrick, we’re a long way from the Suwanee Swifty.’ The fact that he could remember that — I mean of course I would remember a governor putting on deodorant in the parking lot of the Suwanee Swifty — but I have never met another person who has that kind of memory bank,” Meek marveled.

In many respects, the Clintons raised Florida’s stature, treating the budding battleground state as more than a vacation spot. He is the only sitting president to address both chambers of the Florida Legislature.

“They always took Florida seriously. Florida mattered to them from day one,” said U.S. Rep. Debbie Wasserman Schultz of Broward County, who became a leading advocate for Hillary Clinton’s 2008 presidential campaign and later Democratic National Committee chairwoman. Amid this year’s email controversy, she stepped down.

“Yes, her brother lived in Florida and she had that family tie, but more than that. They made Florida a regular fixture in their lives. Major appointments, consistently major events that they came down for. They didn’t treat us like they were checking a box, it’s almost like they made Florida a home state,” said Wasserman Schultz. “And Hillary established herself in her own relationships in her own way. She built a base of support in Florida that she enjoyed herself, not just that was his.”

Miami Herald, 2008
Sen. Hillary Clinton arrives for a fundraiser at Lucky Strike Lanes on South Beach a couple of days before the 2008 Florida presidential primary. From left, she's with Anthony Kennedy Shriver, Philip Levine and then-Miami Mayor Manny Diaz.

Among the biggest gifts President Clinton showered on Florida during his first term was choosing Miami to host the 1994 “Summit of the Americas.” Countless Floridians, from MacKay and Chiles to the Rodham brothers, had lobbied him intensely.

More consequential for Florida’s future was how the state fared during the Department of Defense’s 1993 military base closings. The Pentagon protected MacDill Air Force Base and Homestead Air Force Base from big hits and chose Miami as the new site for the Panama-based Southern Command military.

“We are being treated by the Clinton administration as a first-order state, really for the first time in our history. I think we’re now being treated like California and New York,” crowed Lt. Gov. Buddy MacKay in the summer of 1995, when Democrats started to openly discuss how they might carry the state for the first time since 1976.

The president and first lady seemed to take keen interest in the 1996 re-election campaign.

“When we would do the trip calls, it was always very clear how closely involved the Clintons were,” said Karl Koch, the Florida director, recalling that the first lady campaigned in the state regularly.

“You’d get on the phone with somebody saying, ‘Mrs. Clinton’s going to Pensacola,’ or ‘the president’s going to Panama City,’ and you’d scratch your head and say, ‘Well, okay, that wouldn’t be our first choice, but we’ll make it work.’ Little Rock would say, ‘I know, but this is where they want to go.’”

To help fire up the Florida campaign team, someone printed T-shirts featuring a quote — “It will be a cold day in hell when a Democrat wins Florida” — from Republican operative J.M. “Mac” Stipanovich of Tallahassee.

Clinton carried Florida over Bob Dole and Ross Perot with 48 percent of the vote.

Associated Press, 1994
President Clinton and the first lady answer questions at a health care forum in March 1994 attended by residents of Century Village East.

The brothers

The Tampa Bay Times recently called a phone number we found for Hugh Rodham’s law office. It turned out to be the cell phone of his law partner, Gary Fine.


“Hi, I’m trying to reach Hugh Rodham.”

Laughter. “Good luck with that,” Fine said, even before confirming it wasn’t a prospective client on the line.

Hillary Clinton’s younger brother is her closest and most long-standing tie to Florida, but the campaign declined to make him available for an interview. Nor did he return multiple phone messages, or respond to a note left on his front door in Coral Gables.

“I see Hugh when the president comes to golf once in awhile, but he’s sort of disappeared,” said Gene Prescott, who runs the luxurious Biltmore Hotel in Coral Gables and has been close to the Clintons and their extended family for decades. Friends say Hillary Clinton relied on Prescott to keep an eye on “the boys” and help steer them from controversy.

Associated Press, 1996
Bill Clinton regularly plays golf in Florida, and a favorite spot to stay is the Biltmore Hotel in Coral Gables. Here, in 1996, President Clinton rests his shoulder on Tony Rodham as Hugh Rodham takes a swing.

Hugh, 66, and Tony, 62, moved to Miami-Dade in the early 1980s, and lived in obscurity until Bill Clinton became president. “The boys,” as Clinton aides often called them, shared an apartment until 1986 when Hugh married Maria Victoria Arias, whom he met when she interned at the public defender’s office.

A respected real estate lawyer, Arias, 58, came to Miami with her family after Fidel Castro took over Cuba. The former Republican appeared regularly on Hispanic radio on behalf of the Clintons, flew to the White House to advise on Cuba matters, and to this day gives them a direct line to Miami’s exile community.

Hugh was an assistant public defender when his big sister hit the presidential campaign trail. Tony, who never graduated college, was a private investigator and process server who had worked as a corrections officer, insurance salesman and repo man. Bill Clinton was his ticket into a career common among the politically connected: business consultant.

Friends and acquaintances describe the brothers as engaging and bright, but often blind to conflicts of interest as they tried to capitalize on their Clinton connections. Tony was the ladies man forever aiming to make a big business score, while Hugh was frequently likened to Norm from Cheers.

“She’s devoted to them, but she was harder on them than Bill seemed to be. Bill was more understanding about them being a little — how do I put it — footloose and fancy free,” said Prescott, who partnered on one of Tony’s consulting ventures.

Associated Press, 2001
Bill Clinton plays golf with Hugh Rodham at the Biltmore Hotel in Coral Gables in 2001.

Once Clinton secured the Democratic nomination in 1992, Tony, then 39, went to work for the Democratic National Committee in Washington on constituency outreach. At a bash held by Paul Newman in East Hampton, he met Nicole Boxer, the 26-year-old daughter of California’s new senator, Barbara Boxer.

He moved to Virginia and married Nicole at the White House in May 1994. Dade Circuit Judge Peter Capua, a golfing buddy, presided.

Tony and Nicole had a son in 1995 and divorced in 2000. In 2002 and 2007, she took him to court to collect tens of thousands of dollars in unpaid child support and alimony, according to several news reports. “HILL’S BROTHER A DEADBEAT,” read the New York Post headline.

Even before Clinton’s first inauguration, the Rodham brothers began generating negative headlines. The Wall Street Journal revealed they were soliciting corporations to pay for a series of inaugural parties, which they had to scrap amid public outcry.

Hugh started positioning himself to run for U.S. Senate against popular Republican incumbent Connie Mack III barely nine months into Clinton’s rocky first year in office. Almost nobody in Florida Democratic politics or the White House encouraged him, but few serious candidates wanted to challenge the president’s brother-in-law.

Tony returned to Florida to help his brother, whose campaign immediately ran into trouble. Hugh struggled to explain why, after living in Florida nearly a decade, he first registered to vote for the 1992 election. No candidates had impressed him, he explained, breezily insulting Graham, Chiles and a host of other prominent Florida Democrats.

Hugh had a falling out with his campaign manager after the fellow’s resume turned out to be largely fiction. He also failed to raise much money, never demonstrated depth on issues and faced constant mocking by pundits. “Billy Carter with a law degree,” Republicans called him.

The good news? “I’ve lost 29 pounds in two months,” the former Penn State backup quarterback quipped in May 1994. “My sister said if nothing better comes out of the campaign than that, she’ll be happy.”

Hillary and Bill Clinton showed up at a sparsely attended rally late in the campaign, but Mack won in a landslide with nearly 71 percent of the vote.

Associated Press, 1994
Hugh Rodham challenged popular Republican incumbent Sen. Connie Mack III in 1994, and his sister came down to campaign with him.

Hugh tried talk radio, but that failed to take off. Next, the former assistant public defender who had to take the bar exam multiple times before passing started working on the tobacco lawsuit talks alongside some of America’s most pre-eminent lawyers.

John P. Coale, a Washington lawyer married to TV personality Greta Van Susteren, recruited Hugh. The men denied at the time that political connections landed Hugh the job, though he participated in settlement talks at the White House.

How much Hugh earned from the $1.25 billion settlement in 2002 is unknown, but friends say it ensured he is financially set for life.

That same year, he and his wife upgraded to an $850,000, four-bedroom home in Coral Gables, though any number of solo ventures, or joint ones with his jet-setting salesman brother, could have helped pay for that.

As the clock ticked down on the Clinton administration, the Rodham brothers in 1999 entered into a $118 million venture to export and grow hazelnuts in the Republic of Georgia, partnering with Aslan Abashidze, an archrival of Georgian President Eduard Shevardnadze. Under pressure from an embarrassed White House, they pulled out. Abashidze was later sentenced to 15 years in prison for embezzlement.

Soon after the Clintons left the White House, an uproar ensued over revelations that Hugh had been paid $400,000 to successfully lobby for a presidential pardon for Miami Beach dietary supplement marketer Glenn Braswell, convicted of mail fraud and perjury in 1983, and a prison commutation for California cocaine trafficker Carlos Vignali.

The Clintons said they knew nothing of the lobbying efforts by Hugh, who denied any wrongdoing but agreed to return the $400,000 at the request of his sister and brother-in-law.

“You know, he’s my brother. I love my brother. I’m just extremely disappointed in this terrible misjudgment that he made,” Hillary Clinton said in one of her earliest press conferences as a U.S. senator in 2001.

The brothers periodically accompany their sister on the campaign trail, but they no longer talk to the press. They were last photographed with her in April, campaigning in Scranton, Pa., where their father grew up and they spent summers.

The campaign declined to comment on Clinton’s brothers.

Associated Press, 1994
First Lady Hillary Clinton joins her brother Hugh Rodham at a fundraiser for his U.S. Senate campaign in Miami.

‘You have been there’

The Clintons cherish loyalty, though their poor decisions can put supporters’ loyalty to the test.

MacKay, who did as much as anyone to help Clinton in Florida, needed the president badly in 1998 when he ran against heavy favorite Jeb Bush for governor. The president agreed to campaign and raise money for MacKay, but then the Monica Lewinsky scandal exploded.

On the day independent counsel Kenneth Starr delivered his report to Congress, Clinton came to Florida. Most Democrats stayed away, but Buddy and Anne MacKay stood by their friend that September afternoon in downtown Orlando.

“I don’t think I had a shot anyway at that point, but I had hoped we might be able get some momentum,” recounted MacKay, who quoted Martin Luther King Jr. before introducing Clinton. “In the end, we remember not the words of our enemies but the silence of our friends.”

Associated Press, 1993
Florida Gov. Lawton Chiles and Lt. Gov. Buddy MacKay were close with the Clintons. Here they are with Hillary Clinton at a Florida Democratic Party conference in Orlando in 1993.

Before the crowd in a hotel ballroom, MacKay told the president, “Whenever this state has needed you — through fire, floods, hurricanes and tornadoes — you have been there. We don’t forget that.”

The president looked moved.

“If God lets me live to be an old man, I will never forget what Buddy MacKay said today from this platform when he could have said nothing. And so I hope you will just indulge me for a minute while I say that I thank you for that. I have been your friend. I’ve done my best to be your friend, but I also let you down and I let my family down and I let this country down. But I’m trying to make it right. And I’m determined never to let anything like that happen again. And I’m determined — wait a minute, wait a minute,” Clinton said, cutting the applause. “I’m determined to redeem the trust of people like Buddy and Anne who were with me in 1991. A lot of the rest of you were, too, when nobody but my mother and my wife thought I had a chance to be elected.”

And then came the 2000 election decided by 537 Florida votes.

To this day, friends of Al Gore and the Clintons variously swear that the Clintons lost the election for Gore or that Gore lost it by distancing himself from President Clinton and his record with the economy.

Gore allies maintain Clinton scandal fatigue made him poison with swing voters, so they had no choice but to keep him away. What’s indisputable, though, is at a time when the president could have been focused on ensuring Gore’s election, the priority was Hillary Clinton winning her U.S. Senate race in New York. (She raised more than $300,000 from just over 500 Floridians for that race.)

Berger hosted Bill Clinton’s first Florida fundraiser in 1991, and is Gore’s closest friend in Florida. It’s no accident that in the 2008 Democratic primary, he raised money first for John Edwards and then for Obama.

Associated Press, 1994
The Clinton-Gore ties, celebrated here at the 1994 Summit of the Americas in Miami, frayed during the 2000 campaign. Gore allies maintain Clinton scandal fatigue made him poison with swing voters.

‘Political malpractice’

South Florida is essentially New York’s sixth borough, and Clinton sometimes seemed like Florida’s third senator as she moved toward her presidential run.

She headlined Democratic Party fundraising galas in Orlando and Broward County. She and her husband campaigned for gubernatorial candidate Bill McBride, Sen. Bill Nelson and many more Florida Democrats.

She lamented John Kerry’s loss to Florida fundraisers, privately saying the party had to stop nominating candidates who had little experience or understanding of working-class Americans.

She co-sponsored Nelson’s bill to create a national catastrophic fund to alleviate property insurance costs for Floridians.

And, in 2005, the Clintons attended the Mar-a-Lago wedding of a supportive constituent, Donald Trump.

Getty Images, 2005
Sen. Hillary Clinton and former President Bill Clinton celebrate Donald Trump and his bride, Melania, during their January 2005 wedding reception at the Mar-a-Lago Club in Palm Beach.

In 2008, Florida looked like solid Clinton country. Obama had few Florida ties, and the vast majority of elected Democrats — including prominent African-Americans — lined up behind Clinton. Her strength with women, Hispanics and Jewish voters made her the clear frontrunner for the Democratic primary if not the general election.

“I never for one second thought Hillary Clinton could lose Florida to Barack Obama, and no one else did either,” said Dan Gelber, a former state senator from Miami Beach and prominent Obama supporter during the 2008 primary.

“I think there really is, probably more than any other state except maybe New York and Arkansas, a real connection between Florida and the Clintons,” said Gelber, noting that his mother, like many Jewish mothers and grandmothers across South Florida, has a picture of herself and Hillary Clinton prominently displayed in her home.

Times files, 2006
HIllary Clinton headlined Democratic Party fundraising galas across Florida as a senator from New York, including this one at the Wyndham Westshore in Tampa.

A fateful decision helped cost Clinton the nomination.

Democratic activists in the early voting states of Iowa, New Hampshire and South Carolina resented Florida stealing their spotlight by scheduling its primary earlier than allowed under national party rules. They asked the candidates to sign a pledge not to campaign for Florida’s primary, rendering the vote officially meaningless because no delegates would be awarded. Obama’s campaign helped craft the deal knowing Clinton would be tough to beat here.

Clinton signed the pledge, effectively boycotting Florida’s Democratic primary. It was another Clinton calculus: Better to snub Florida’s Democratic voters and activists temporarily, than risk alienating party regulars in all-important Iowa and New Hampshire who could really derail her campaign. She and her campaign advisers assumed they’d dispatch Obama anyway and the Florida question would be moot.

Except she lost the Iowa caucuses.

“Political malpractice,” former Clinton campaign adviser Mo Elleithee said recently of that decision.

Suddenly in deep trouble after the Iowa loss, and with her husband causing distractions by periodically popping off angrily on TV, Clinton phoned U.S. Rep. Kendrick Meek. She needed a favor.

“She said, ‘Bill needs someone to travel with. You like him, he likes you, and you two would be good together,’” recalled Meek, who for months accompanied the former president on his primary state travels, helping keep him grounded during long days on the trail and long nights playing cards.

Clinton overwhelmingly beat Obama in Florida’s officially meaningless primary, which meant she received no delegates.

Months later, the Clinton-Obama race became a fight for every delegate and Clinton suddenly wanted to stand up for the rights of “disenfranchised” Florida Democrats who voted in the primary. The DNC awarded her some delegates from Florida, but not enough to help her overcome Obama.

Associated Press, 2008
When the 2008 Democratic primary dragged out between Barack Obama and Hillary Clinton, she wanted to stand up for the rights of “disenfranchised” Florida Democrats and get their votes to count. A candidate boycott rendered the primary meaningless.

Not new at all

Eight years is a long cooling off period. Passions over past campaigns are gone.

“Everyone has moved on, and everyone is working together now,” said Berger, who hosted a Clinton fundraiser earlier this year.

The Clintons never ceased being a part of the fabric of Florida politics, building new relationships — and burnishing old ones.

Bill Clinton campaigned tirelessly for Meek when he ran for U.S. Senate in 2010, and stayed by his side when Meek declined to step aside for Charlie Crist. He also campaigned for Alex Sink for governor in 2010 and for Crist for governor in 2014.

Octavio Jones | Times
Tampa Mayor Bob Buckhorn and former Gov. Charlie Crist listen as HIllary Clinton addresses supporters in July at the Florida State Fairgrounds in Tampa.

Three decades have passed since Hillary Clinton introduced herself to Florida as part of a couple representing a fresh, new direction for the Democratic Party. That was before the Internet, before the Florida recount, before Jeb Bush and the GOP took over Florida politics, before the war on terrorism and before reality TV.

Democrats are nearly irrelevant in Tallahassee these days, but favored to win their third Florida presidential election in a row.

“I’m not new to this area or its concerns,” Clinton told supporters at St. Petersburg’s Coliseum in August, reminding them that she had rallied supporters at the same venue 20 years before.

Not new at all. By now, Clinton knows Florida about as well as anyone. Many Floridians know her, too, or at least think they do. If she loses this state in November it won’t have anything to do with unfamiliarity.

Times researchers Caryn Baird, Carolyn Edds and John Martin contributed. Contact Adam C. Smith at [email protected]. Follow @adamsmithtimes. Designed by Lauren Flannery. Photo editing by Patty Yablonski.

Octavio Jones | Times
Days before she would become the first woman nominated for president by a major party, Hillary Clinton shook hands with supporters at the Florida State Fairgrounds in Tampa.

Hillary Clinton’s Florida connections


Alvin Brown: Bill Clinton stayed loyal to his former aide, campaigning repeatedly for him when he won election as Jacksonville's first black mayor in 2011.


Buddy MacKay: The former lieutenant governor came to know Bill Clinton through education reform efforts in the 1980s and chaired his Florida campaign in 1992.


Richard Swann: He is a longtime Democratic fundraiser whose daughter is married to Virginia Gov. Terry McAuliffe, another top Clinton money-raiser and ally.
Dick Batchelor: The consultant and former legislator was among the earliest Clinton supporters in 1991.
Jim Pugh: Another veteran Democratic fundraiser and longtime Clinton backer.
Bill Nelson: He and his family bonded with the Clintons over Renaissance Weekends in the 1980s and a prayer group the senator’s wife, Grace Nelson, helped lead in Washington.


Arthenia Joyner: The state senator and civil rights pioneer has known the Clintons since the 1980s through the National Bar Association.
Bob Buckhorn: This Tampa mayor was among the earliest Bill Clinton supporters in Florida in 1991.
Sandy Freedman: This Tampa mayor was also among the earliest Bill Clinton supporters in Florida in 1991.
Ana Cruz: The Democratic operative has been with the Clintons from the start. She helped lead a stealth Hillary Clinton primary campaign in 2008 when the candidates were shunning Florida because its primary was scheduled earlier than allowed by the national party.


Doug Band: The former Sarasota resident and University of Florida grad interned in the Clinton White House and then became an adviser, assistant and gatekeeper to Bill Clinton. He helped found and oversee the Clinton Foundation, and now is a wealthy New York-based business consultant.


S. Daniel Abraham: The billionaire behind the Slim-Fast line is another longtime and generous pal of the Clintons.
Alfonso "Alfy" Fanjul: The wealthy sugar magnate was an early and longtime friend of the Clintons.
Alcee Hastings: The congressman is a longtime Clinton friend and ally.


Joe Geller: Used to lead Miami-Dade's Democratic Party and was a key organizer for Clinton in 1991.
Nan Rich: The former legislator has known Hillary Clinton since she helped the first lady set up a pre-K program in Arkansas.
Debbie Wasserman Schultz: A longtime Clinton ally and supporter, she was one of Hillary's top campaign surrogates in 2008 and eventually was tasked with trying to unite hurt Clinton supporters behind Barack Obama.


Hugh Rodham: Hillary's brother, a former public defender and an unsuccessful U.S. Senate candidate in 2004.
Ira Leesfield: The former Academy of Trial Lawyers chief and his wife, Cynthia, have been pals with the Clintons from the start.
Kendrick Meek: The former state trooper and congressman is almost like a son to Bill Clinton and was a top adviser to Hillary Clinton in 2008.
Chris Korge: No one is closer to the Clintons in Florida and almost nobody in America has raised more money for Hillary Clinton.
Alex Heckler: At 40 one of the youngest of Hillary Clinton's Florida pals, Heckler became a top tier money-raiser in 2008.
Elaine Bloom: The former legislator and liberal stalwart was one of the earliest Clinton supporters in 1991.
Philip Levine: The businessman and Miami Beach mayor became close friends with Bill Clinton after he left office and has traveled to countless countries with him.