The Second-Strangest Campaign of the Season Is Taking Place in Florida, of Course

Florida Congressman's Grayson bid for Senate
Grayson, at a children’s center in Sunrise, Florida, hoping to be taken seriously. Photo: Dina Litovsky/New York Magazine
And it’s taking place in Florida, of course.
Photograph byDina Litovsky
Grayson, at a children’s center in Sunrise, Florida, hoping to be taken seriously.

“Before I even got into the race, one of Murphy’s donors and I had lunch together and he told me, ‘If you run, they will destroy you.’ I asked, ‘Who’s they?’ And he said, ‘Harry Reid and the DSCC [Democratic Senatorial Campaign Committee].’ They’re certainly doing their best.”

Alan Grayson, the Florida representative and liberal firebrand hoping to win Marco Rubio’s U.S. Senate seat, was attempting to explain the recent avalanche of explaining he’s had to do as he runs in the Democratic primary against his congressional colleague Patrick Murphy, the preferred candidate of the Democratic Establishment. About, for instance, the $16 million Cayman Islands hedge fund that he’s been operating as a sideline to his congressional duties (which Grayson insists is a “family investment partnership” registered in the offshore tax haven only because “the securities lawyers told us we had to do it that way”). Or about the 2015 annulment of his 25-year marriage to Lolita Grayson, the mother of his five children, who, it turned out, was not yet divorced from her first husband when she wed Grayson in 1990. (“I’ll sum it up for you,” Grayson told an Orlando television station in the midst of his nasty court battle with Lolita. “Gold diggers gotta dig.”)

Grayson, who is 58, is a large slab of a man with a giant head that wouldn’t look out of place on Easter Island and a mincing, splayfooted gait that resembles that of a penguin. Throw in his customary wardrobe of garish cowboy boots and novelty neckties that feature everything from Monopoly money to rainbow peace signs, and he doesn’t call to mind a congressman so much as the villain in a Batman movie. He’s the only member of Congress whose desk is decorated with a plaque that reads: I HAVE FLYING MONKEYS AND I'M NOT AFRAID TO USE THEM!

He blames the bad headlines and the ensuing congressional ethics investigation into his hedge fund — sorry, his family investment partnership — on researchers working for his opponent. “Murphy has a staff of five people in communications who literally do nothing but call people all day long and try to throw dirt on me,” he said. And according to a confidant, he also suspects Murphy and his allies may have been behind the almost two-year court battle over his annulment, especially since the final two of the six lawyers Lolita worked with are from Murphy’s stomping grounds in South Florida.

Grayson in Boynton Beach, Florida. Photo: Dina Litovsky / Redux

Now, on a recent morning in his Capitol Hill office, Grayson was getting ready to explain away more bad news. His press secretary had just forwarded him an email from a Roll Call reporter who had some questions about the congressman’s investments in Petrobras, the state-owned Brazilian oil company currently embroiled in a massive corruption scandal. “I’ve traded probably between a quarter-billion and half a billion dollars’ worth of stock,” Grayson told me, sounding both boastful and aggrieved. “There’s only like 20,000 publicly traded companies in the entire world, so there’s a good fraction of them that I’ve traded at one time or another.” He owned Petrobras stock, he speculated, “maybe five years ago. Maybe more. I don’t even know. Certainly it’s likely before the quote-unquote corruption even took place.”

Of course, Grayson knew that answer wouldn’t satisfy the inquiring reporter. He grew more annoyed. “Somebody on my staff is going to have to dig out the Petrobras records and find out what year I bought the stock in and when I sold the stock. And then we’re going to have to go on Google and find out when the corruption took place, or whatever. And then we’re going to have to point out to this guy that whatever Murphy’s people told you, nobody knew, nobody could have known, blah blah blah blah blah.” His voice trailed off. “And this happens over and over and over again.”

If Grayson were simply running for reelection in the House, none of this would present a huge problem. He represents a heavily Democratic congressional district anchored in Orlando, and his stridently lefty politics have made him extremely popular there. “Maybe Barack Obama could beat me in a Democratic primary in Orlando,” he concedes. “Maybe.

But Grayson wants to be a senator, and so he’s found himself in the middle of the second-most-bizarre campaign of this election season. Last month, Rubio, fresh off a period of soul-searching immediately following the Orlando massacre and two days before the filing deadline, discovered he does not wish to retire from the Senate after all. (“I have only said like 10000 times I will be a private citizen in January,” he tweeted in May — but that was May.) This transformed the race from an open seat that favored the Democrats to one that may be harder for them to win but comes with a more delicious prize: finishing off Rubio for good. “Rubio’s career in electoral politics will be over if he loses this November,” predicts Eric Jotkoff, a Florida Democratic operative. Removing one of the GOP’s most promising political athletes from the playing field would also help Democrats take back the Senate — and win the White House.

But Grayson presents a problem. “Florida never elects Alan Grayson,” John Morgan, an Orlando trial lawyer and major Democratic fund-raiser, tells me. “It just doesn’t happen.” This is a widespread belief among Democrats throughout Florida and Washington. Harry Reid has called on Grayson to drop out before the August 30 primary, declaring that “his actions aren’t just disgraceful to the Democratic Party, they disgrace the halls of Congress.” Joe Biden stumped for Murphy in May, proclaiming him “the real deal.” Last month, President Obama spoke at a Murphy fund-raiser in Miami — one of many high-dollar events that Murphy advisers believe will allow them to spend as much as $8 million in his primary campaign against Grayson. And for the first time, the leading Democratic Senate super-pac has waded into a primary race, already having spent $1 million on television ads for Murphy.

In response, Grayson has deployed the monkeys. Having initially gained a national following among progressives for the verbal beat-downs he routinely delivered to Republicans — once likening the tea party to the Ku Klux Klan and calling a female adviser to then–Federal Reserve chairman Ben Bernanke a “K Street whore” — Grayson has now trained his fire on his fellow Democrats. When Reid visited the Congressional Progressive Caucus in May, Grayson hijacked the meeting by angrily confronting the Senate minority leader. “Say my name, Senator!” Grayson demanded, as his colleagues looked on in embarrassment and horror. “Say my name!” Later, Grayson derided Reid and his allies as “Mafia accountants with Napoleonic complexes.”

Grayson currently trails Murphy in the polls, but if he loses the primary, he seems intent on bringing Murphy down with him. “He’s a 33-year-old nobody who’s done nothing in his life,” Grayson told me. “He’s never had a serious relationship, never married, no children, never had to support himself, never had a real job, and lived off a trust fund on his daddy’s yacht for the first 30 years of his life.” He wasn’t finished. “He’s a zero, an absolute zero.”

Rubio, scrambling to remain in the institution from which he wanted desperately to escape. Photo: Mark Peterson/Redux

When Marco Rubio slunk back into the Senate chamber in March, the man once hailed as “the Republican Savior” by Time had been downgraded to “Liddle Marco,” courtesy of Donald Trump. (“It’s spelled L-I-D-D-L-E,” Trump made sure to clarify.) It had been only a few months since Bill Clinton had deemed no one more formidable in a general election against Hillary, but Rubio’s White House run had turned into a series of humiliations, climaxing in getting poleaxed by Chris Christie in a February debate. By the time Trump trounced him by 19 points in Florida, Rubio was a politician who’d lost his mojo. “For a long time, Rubio was a blank slate where Republicans projected their greatest hopes and Democrats projected their greatest fears,” says Dan Pfeiffer, the Obama White House’s former communications director. “But as it turns out, he’s just a blank slate.” The fact that Rubio would now have to spend the next nine months as a lame duck made his situation even bleaker.

Rubio was first elected to public office in 1998, when he was just 26, and he’s been seemingly terrified by the prospect of the private sector ever since. In 2008, as he approached his term limit in the Florida State Legislature, he desperately searched for another office for which he could run. “People aren’t going to forget you,” a political ally reassured him, as McKay Coppins recounts in his recent book The Wilderness. But Rubio was not consoled, instead launching a long-shot bid for Florida’s open U.S. Senate seat against the incumbent GOP governor, Charlie Crist.

The proverbial young man in a hurry is now 45, and, while his ambition is as palpable as ever, he wears it less gracefully. Rubio’s supporters say he really was looking forward to taking a break from elected office and making some serious money; he’d even hired the famed Washington lawyer Robert Barnett to field offers, which one Rubio friend told me were “numerous and lucrative.” They maintain that his decision to run for reelection was as sincere as it was sudden. “Marco had no plans to reorient to the Senate,” an adviser says. But in retrospect it appears Rubio had been laying the groundwork for reversing his decision as early as March. His interest in Florida-specific issues and attention to Florida media outlets, both notoriously lacking for much of his term, suddenly ratcheted up. Once withering in his contempt for the legislative branch — “We’re not going to fix America with senators and congressmen,” he told an Iowa town hall in January — he was now unstinting in his praise for the world’s greatest deliberative body. “I’m honored to serve in the Senate,” he told Politico in May.

And sometimes personal ambition syncs up with political gravity. With private polling suggesting that any of the five existing Florida GOP Senate candidates would lose in November, the man who couldn’t manage to get his party to coalesce around his presidential candidacy was suddenly the target of a ferocious lobbying effort from Senate Majority Leader Mitch McConnell and other top Republicans to run for reelection. These Republican heavy hitters assured Rubio that money wouldn’t be a problem — especially since a number of GOP donors would direct the money they refused to spend on Trump’s presidential bid to Rubio’s Senate run. They appealed to Rubio’s vanity, telling him that he could become a party hero by helping to save the GOP’s Senate majority in the coming anti-Trump wave. And they intimated that should Rubio not heed their calls, they’d have long memories when, four or eight years from now, he came seeking their support for an inevitable second run at the White House. “They used every lever imaginable,” says one prominent Republican operative. (Even Trump got into the act, tweeting “Run Marco!” in late May.)

Rubio also knew, from painful personal experience, that although Murphy was racking up support from his own party’s leadership, 2016 is not a great year to be an Establishment favorite. Unlike Republicans, Democrats are going into this month’s convention having managed to beat back populist insurgencies, both at the presidential level and in down-ballot races. (In Maryland, Ohio, and Pennsylvania, the Democratic Establishment candidates won their contested Senate primaries; in the handful of House primaries in which Bernie Sanders endorsed a candidate, the only one to win so far has been New York’s Zephyr Teachout.) Yet the energy of the party — and possibly its future — clearly resides with the populists. “You get the feeling sometimes,” one prominent Democratic donor on Wall Street recently told me, “that the barbarians are at the gate.”

Rubio still has to win the GOP primary against Carlos Beruff, a millionaire real-estate developer (think a cut-rate version of Trump). But with a 64-point lead in the polls, he has the luxury of positioning himself as above the fray and in opposition to both of the highly disliked presidential candidates. Having gone from calling Trump a “con artist” (February) to pledging to support him (May), Rubio now says it’s his duty to remain in the Senate and “act as a check and balance on the excesses of the next president.” And, of course, Rubio is thinking about his own, still burning presidential ambitions. “Having a platform in the Senate will be pretty valuable,” explains a Rubio adviser. “Let’s say Hillary is elected. Marco will be a major player when her secretary of State nominee has his confirmation hearings. It’ll be much more powerful to be prosecuting your case from the purview of the Senate Foreign Relations Committee than from a Fox News studio.”

Flush with cash and bolstered by near-unanimous party support, Rubio is already enjoying his reversal of fortune — now he’s the one watching a primary race in which a clownish interloper pokes mercilessly at an inexperienced party man. “You can’t believe anything [Murphy] says,” Rubio told Politico last month. And as for Murphy’s opponent: “Alan Grayson is insane.”

Grayson would dispute the insanity charge but cop to being unconventional. Born and raised in the Bronx, the son of two New York City public-school teachers, he worked as a janitor and a security guard to pay for his three Harvard degrees (undergrad, law, and public policy). Now the 12th-wealthiest member of Congress with a net worth of $34 million, he made his fortune as the president of a discount-calling-card company and then as a trial lawyer. It was in his latter job that he began bringing whistle-blower suits against Iraq War contractors, which, in turn, led him to politics.

In 2008, he ran as a stridently antiwar candidate and beat a Republican incumbent in a suburban-Orlando swing district. During the Obamacare debate on the House floor, he described the Republican health-care plan as “Die quickly.” Grayson lost his seat two years later in the GOP’s midterm wave, but he returned to Congress in 2012 by running in a newly created — and more Democratic — Central Florida district.

Even in a town and a profession rife with self-promoters, Grayson stands out as an incorrigible publicity hound and credit hog. He’s notorious among his congressional colleagues for referring to pieces of legislation that they introduced but he merely co-sponsored as “Grayson bills.” Nor is he shy about placing himself at the center of important events. He claims that he was the person who suggested to Republican congressman Mark Meadows that Meadows employ an obscure parliamentary tool that ultimately led to John Boehner’s stepping down as Speaker of the House. (“I enjoy working with all of my colleagues,” Meadows told me, “but Mr. Grayson must have been confused about any conversation he had with me on the topic.”)

In the era of the humblebrag, Grayson prefers to eschew subtlety. When I once asked him about his political heroes, he replied, “I think it’s safe to say that Robert Kennedy and I are the only ones in public life who are likely to quote Aeschylus at any given moment.” A few minutes later, Grayson was, unbidden, tallying the YouTube views of a video of him questioning the inspector general of the Federal Reserve during a 2009 congressional hearing. “There’s one version with 4-plus million views and another version with 1-plus million views, plus a whole bunch of other spinoff versions,” he reported. “Just those two alone, it’s 5 million views — way more than any other video in the history of Congress!” More than one person has branded the congressman “the Trump of the left.”

And that’s not even taking into account his messy personal life. During the time in which he was seeking an annulment of his marriage to Lolita — or, as he now refers to her, his “ex-non-wife” — Grayson began dating a Florida woman 13 years his junior named Dena Minning, whom he met on a flight from Orlando to Washington, D.C. Last summer, shortly after Grayson announced that he was running for the Senate, Minning announced that she was running for Grayson’s House seat. Then, this past Memorial Day weekend, Grayson and Minning were married in a small, private ceremony on a Florida beach. Grayson told me that the hush-hush nature of their nuptials — the couple didn’t even dare to have a chuppah for fear of drawing unwanted attention — was because “if there had been any sort of hint that we were going to do it publicly, then I would have had a tracker [from Murphy’s campaign] at my wedding.”

A few weeks later, the newlyweds appeared together at a resort just north of Miami for the Florida Democratic Party’s annual gala. “Welcome to our honeymoon!” Dena exclaimed when we met. A petite woman with long blonde hair and the perky demeanor of a gymnastics coach, she managed to remind me five times in the first ten minutes of our conversation that she has both a medical degree and a doctorate. (To wit: “Sorry, M.D.–Ph.D.,” after a brief and entirely comprehensible discussion of the political and medical challenges posed by the Zika virus.) She denied that there was any awkwardness in seeking her “beautiful, awesome” husband’s House seat, even though one of her primary opponents ran her husband’s district office. And she maintained that there was absolutely no political calculation behind her decision to get married before the primary, so that she might appear on the ballot as a Grayson. “We’re a team,” Dena added. “Team Grayson.”

I asked her if she’d faced any of the same institutional hurdles her husband was facing in his Senate race. Alan, who was sitting next to her and tightly holding her hand, answered for her.

“I am the institution,” he told me. “There is a machine [in his congressional district], and it’s the Grayson machine.” In early July, Dena’s campaign aired its first TV ad — narrated by her husband.

Grayson at a house party for supporters and leaders in Boynton Beach, Florida. Photo: Dina Litovsky / Redux

But for all Grayson’s bombast and buffoonery, the Trump-of-the-left line isn’t really fair. A better comparison might be Bernie Sanders in Floridian drag. When Grayson arrived in Congress in 2009, he was assigned a seat on the House Financial Services Committee. Democratic and Republican leaders often put their freshmen members from swing districts on Financial Services since it’s a surefire way for them to raise gobs of money for what will likely be tough reelection campaigns. Grayson had other ideas. Instead of using his Financial Services perch to buck-rake — the words Goldman and Sachs appear nowhere in his FEC reports — he used it to rake Wall Street over the coals. He introduced a bill restricting salaries and bonuses for executives at financial institutions that had received federal bailout money. (The bill passed the House and died in the Senate.) He subjected Wall Street CEOs, as well as Treasury Department and Federal Reserve officials, to withering cross-examinations at committee hearings.

Grayson is such an effective interlocutor because he is shockingly smart. “I believe that he’s almost Asperger’s smart, which is a really great way to be smart until it comes to dealing with people,” says John Morgan, who was a friend and supporter of Grayson’s before they had a falling out over his favoring Murphy in the current race. A former congressional aide recalls an occasion when Grayson was talking to an attorney from the House’s legislative-counsel office about a piece of legislation Grayson wanted to introduce: “Grayson was reciting from memory parts of the federal code, and he was correcting the guy whose job it is to draft that part of the code.” He seeks out similarly intelligent people for his staff, even if they’re unconventional hires. Aaron Swartz, the brilliant young internet activist who killed himself after being indicted on federal hacking charges, worked as an intern in Grayson’s congressional office.

Although it’s difficult to get much done as a Democrat in Congress these days, Grayson has taken a page from the playbook Sanders employed when he was in the House and become the body’s “amendment king.” He’s similarly tenacious about signing up co-sponsors for his legislation, circulating on the House floor and collecting co-sponsors’ signatures. The whole exercise can feel a little Model U.N. (members usually use their staff to drum up co-sponsors) and a little futile (it’s doubtful any of his bills will pass in a Republican House). But Grayson does little to hide his contempt for his colleagues who roll their eyes at him.

One afternoon on Capitol Hill, Grayson sat outside the House chamber as he waited his turn to place one of his amendments. “Most people who are here, on both sides of the aisle, are basically career politicians who were elected to City Council and then after that they got to be mayor and then after that they got to be state representative and then state senator and here they are,” Grayson said. “It’s the next rung up the ladder, and they’re just looking to get the pension at the end of the gig. That’s all.

“I want to get good stuff done, stuff that means something,” he continued. “There’s a lot of members who just don’t have the intellectual caliber to be able to do that, and there’s other members who just don’t give a shit.”

I asked him what percentage of members he thinks fall into the category that he puts himself in.

“Five percent,” he said.

I asked what percentage lacked the intellectual caliber to do their job.

“Two-thirds,” he replied. “There’s a talent deficiency in this institution. There’s no IQ test to serve in Congress, that’s for damn sure.”

Murphy, spending what it takes and making lots of new friends. Photo: Dina Litovsky/New York Magazine

Patrick Murphy isn’t nearly as jaded. “It’s so frustrating because a lot of the members of Congress, Republican and Democrat, are actually really good people,” he told me last month when we sat down at the Florida Democratic Party’s weekend conference in Hollywood. “They really do care. They really do want to make a difference. They’re in it for the right reasons. They’re family people. They’re honest. They’re hardworking — all those traits. But there are some bad apples that ruin it for both sides.”

Murphy considers Grayson one of those bad apples. “He’s in pretty big trouble,” Murphy elaborated, referring to the reports about Grayson’s hedge fund. “Obviously there’s the serious ethics investigation, and he’s continued to live this sort of lie of a career and bluster and bully and then has a completely different life going on that I don’t think he wants people to know about, clearly.”

Murphy has red hair, broad shoulders, and the towel-slapping bonhomie of the college-baseball prospect he was only 15 years ago. The son of a construction magnate, Murphy initially followed his father into the GOP. In 2007, he made a $2,300 campaign donation to Mitt Romney’s presidential campaign. “When I first go to register to vote,” Murphy told me, “you know, ‘Hey, my dad’s a Republican, I guess I’m a Republican.’ I mean, it’s maybe not the right way to do it, but I think it’s how a lot of people probably do it.” Murphy explained that the subsequent rise of the tea party persuaded him to become a Democrat. In 2012, he decided to run for Congress. Fortified by $550,000 in donations from his father, Tom, to two super-pacs supporting his candidacy, Murphy beat the tea-party darling Allen West by fewer than 2,000 votes in what was that year’s most expensive House race. He was assigned to a seat on the Financial Services Committee, which he used to hoover up campaign donations. With a campaign war chest of $5.2 million in 2014 — the second-largest of any Democratic House candidate that year — Murphy won reelection by almost 20 points.

It wasn’t long after that victory that Murphy began feeling out prominent Florida and national Democrats about running for the Senate. In many ways, he fits the profile of the type of moderate Democrat party elders believe they need in order to win statewide races in Florida — which only one Democrat, Senator Bill Nelson, has managed to do in the past decade. Ranked among the most conservative House Democrats by National Journal, Murphy voted in favor of the Keystone XL Pipeline and tougher security checks on Syrian refugees. Democratic kingmakers were impressed with his office’s constituent-services operation. “He’s gotten stuff done for his district,” the Florida Democratic strategist Eric Jotkoff says. “He’s been a champion of the Indian River Lagoon and the water issues there.” They also respected the elbow grease he showed in seeking their endorsements. “We busted our tail trying to get that support from everybody,” Murphy told me. It didn’t hurt Murphy’s cause that his father began giving generously to other Democrats. In the past few years, Tom Murphy has given hundreds of thousands of dollars to Democratic candidates and their affiliated super-pacs.

All of which has amounted to something of a Murphy juggernaut. His campaign currently has more than two dozen paid staffers, including some of the country’s top Democratic operatives. “He has the luxury to spend what he’s got to in the primary,” says Steve Schale, a Florida operative who helped run Obama’s presidential campaigns there, “so he will be able to blanket the airwaves and introduce himself and Grayson to Florida voters.”

Grayson finishes speaking at the Democratic caucus at the Diplomat Hotel in Hollywood, Florida. Photo: Dina Litovsky / Redux

As the candidate made the rounds at the Florida Democrats meeting in Hollywood, he was accompanied at all times by a phalanx of three or four aides. “Patrick hates having an entourage,” one of them assured me, as Murphy hustled from the Hispanic-caucus meeting to another being held by the Caribbean caucus. But the entourage never thinned. At each stop, Murphy made the same pitch of protecting Social Security and the environment. In interviews, he emphasizes that he and Grayson are not that far apart ideologically. The difference, he argues, is one of temperament.

That afternoon, a few hours before the Florida Democrats would gather for their gala dinner, Murphy’s campaign commandeered a hotel ballroom to host a press conference. It would feature a special appearance by New Jersey senator Cory Booker, who was joining Murphy for his announcement of proposals related to criminal-justice reform, an issue Booker has championed in the Senate. Reporters arrived to find a spiral-bound booklet titled “The Murphy Roadmap” on their seats. It consisted of seven pages, in a large font with wide margins, and offered vague proposals like “empowering students” and “strengthening our communities.” Murphy’s elaboration of those proposals was anything but eloquent. He has a halting public-speaking style and a tendency to mispronounce 50-cent words. (Grayson, according to Murphy, isn’t bombastic but “boombastic.”) He also has the unfortunate millennial verbal tic of punctuating sentences with the query “right?” A plea for better citizen-police relations comes out of his mouth as “We must ensure police and the communities they serve actually trust each other, right?”

A reporter asked how more data collection, which the candidate’s road map called for, would help improve policing, and Murphy gave a meandering answer about the need to poll communities about what they think of law enforcement. “What this does is find the data where the trust has broken down in our relationships there,” he said.

“I just want to add something,” Booker interjected, going on to explain that it can also be helpful to have data on police-involved shootings.

The spotlight that comes with a national Senate race has not been kind to Murphy. In the past two months, as reporters have begun to dig into his biography, they’ve discovered a number of discrepancies. Although his congressional and campaign websites claimed that he’d earned dual “degrees in accounting and finance” from the University of Miami, he possesses only a bachelor’s degree in business administration. Murphy has repeatedly touted his pre-congressional work as a certified public accountant with Deloitte & Touche in Miami. (“I would be the second CPA in the history of our country to serve in the Senate,” he told me. “I mean, crazy.”) But an investigation by Jim DeFede of CBS revealed that Murphy worked as a CPA for Deloitte & Touche for less than a year and had obtained his CPA license in Colorado, which has less stringent requirements than Florida — and then only after he’d taken the licensing exam multiple times. Murphy has touted his experience as a “small-business owner” who, in the wake of the Deepwater Horizon oil disaster in 2010, founded a firm to help clean up the Gulf of Mexico. But DeFede’s investigation showed that the company was actually just a subsidiary of Murphy’s father’s firm, Coastal Construction. “He was never a small-business owner,” DeFede concluded.

The CBS investigation, which aired in late June, rattled some Democrats, but Murphy’s supporters now say it won’t leave a permanent mark. “You’re dealing with Florida, where more people probably watch Jim DeFede’s show in D.C. than they do in Miami,” one prominent Florida Democrat told me. “Florida is paradise. Nobody tunes into that stuff.”

Perhaps, though, the episode suggests that national Democrats did not vet Murphy as carefully as they should have. Indeed, Grayson says that after he failed to get Joe Biden to endorse him — or at least not endorse Murphy — the vice-president called him to explain. “He started saying, ‘Well, Patrick is not as right-wing as you made him out to be,’ ” Grayson recalls. Grayson says Biden specifically mentioned Murphy’s stances on gay-rights issues and his leadership on repealing the military’s “don’t ask, don’t tell” policy. Grayson says he was puzzled, since Murphy hadn’t been elected to Congress when the policy was repealed in 2011, but he let Biden get off the phone. It was only later that he realized the vice-president had been talking about the voting record of a different Patrick Murphy, who represented Pennsylvania in Congress from 2006 to 2010 (Biden’s office denies this).

Alan Grayson in Sunrise, Florida, in June. Photo: Dina Litovsky/Redux

As the Republican Party gathered in Cleveland for their convention, Rubio was a thousand miles away in Florida, doing a six-day campaign swing up and down the state. Still, Trump casts a long shadow. Although a poll in mid-July showed the incumbent beating Murphy by 13 points and Grayson by 12 in head-to-head matchups, Rubio’s team knows that Trump could scuttle Rubio’s Senate aspirations just as he crushed his presidential ones. “The challenge is we have no idea how Trump will do in Florida,” says one Rubio adviser. “If Trump doesn’t do well, Marco’s still probably fine. But Trump can’t collapse in Florida. There’s just not a lot of precedent for a down-ballot candidate in a purplish state running double digits ahead of the top of the ticket.”

This is the prospect that gives Florida Democrats hope as they stare down another five weeks of two less-than-ideal candidates mauling each other in a vicious primary fight. When he hasn’t been in Nantucket onboard his father’s yacht Cocktails, Murphy has spent much of July attending high-dollar fund-raisers and basing the case for his candidacy primarily on the merits of his endorsers. Grayson’s fund-raisers are less cushy. At one, where he collected $50 checks from a few dozen people, he devoted most of his remarks to tearing into Murphy. A supporter asked when the two would debate. “It’ll never happen,” Grayson replied. “His father would never give him permission to go out that night. He never wants to get too far from his juice box.”

It’s a weird thing to say about a gauche self-aggrandizer with a Cayman Islands hedge fund, but Grayson appears to be the only candidate in the Florida Senate race not wholly consumed by his own political ambition. His primary motivation for running, it seems, is because he doesn’t believe Murphy is worthy of the office. “There’s no reason Patrick Murphy deserves that kind of favoritism. He’s done nothing — in life or in Congress,” he told me. “I’ve never seen anybody make any serious effort to justify why Patrick Murphy should be one of two people representing 20 million people in the U.S. Senate.”

Grayson has spent a considerable amount of mental energy envisioning what he’d bring to the Senate. “There are many, many issues in the Senate that are resolved only by unanimity, which means that if you are the squeaky wheel, you can get a lot of grease,” he says. “I could work that system even better than I work the House system.” He fears that if Democrats don’t do a better job responding to angry voters, they’ll suffer the same fate as Republicans. “The party has been taken over by corporate Democrats,” he says. “Our party has to a large degree abandoned the whole concept of trying to improve people’s lives.”

At the Democrats’ gala, Grayson watched as Booker, the evening’s keynote speaker, charmed the crowd. “The Senate is doing pretty good with one Murphy right now,” Booker said, referring to Connecticut’s Chris Murphy. “What the hell, let’s have two!” Soon, Booker’s witty banter morphed into something akin to a performance at the Moth, as he told the harrowing tale of a teenager dying in his arms after being shot in Newark. “Another black boy is dead and who cares?!” Booker recalled thinking, his voice still choked with rage. “I tried to start rubbing his blood off my hands,” he said, holding them above the podium. “I jumped in the shower, I turned it on as hot as I could possibly take it, and I just stood there and my insides were breaking. I was so angry at us!”

When the speech was over, the crowd gave Booker a standing ovation. Grayson sidled up to me. He was one of the only people in the room not clapping. Bending at the waist, he whispered in my ear, “You will hear exactly the same speech, word for word, down to the hand gestures, at the Democratic National Convention.”

*This article appears in the July 25, 2016 issue of New York Magazine.