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Illustration by Clay Jones

In his bid to unseat Darren Soto, Alan Grayson is as unfiltered as ever. But progressives seem tired of his schtick 

U.S. Rep. Darren Soto’s phone was buzzing nonstop inside the small, dimly lit lobby of the Super 8 motel.

Moments before, officials with the Federal Emergency Management Agency confirmed the news: FEMA would pay for Puerto Rican evacuees displaced by Hurricane María to stay for five more nights at hotels on the order of a federal judge.

FEMA, though, didn’t immediately tell the hotels – and some managers had started kicking families out at checkout time. Using the Super 8 on Highway 192 as a base, Soto and his staff worked to get the word out about the new deadline. At times, Soto rushed out of the lobby into the early July heat and drove down the Kissimmee tourist strip, stopping at hotels to make sure families weren’t being asked to leave. “This will give us a few more days to hopefully get some of these families that have been more difficult to place a place to go,” the Orlando Democrat told reporters.

This is how it had been for months. Tens of thousands of people fled after the storm destroyed their homes in September, most ending up in Florida. FEMA gave Puerto Rican evacuees hotel vouchers that were renewed monthly. Every two weeks, displaced families would wait anxiously for FEMA to tell them if they were allowed to stay or whether they'd need to find their own shelter – a difficult task given that affordable housing is scarce.

Soto's staff had helped get extensions for individual cases while Soto joined Florida lawmakers in sending letters and calling out FEMA officials for underfunding aid to Puerto Ricans.

For Alan Grayson, that wasn't enough.

The bombastic firebrand who used to represent Soto's congressional district before leaving in 2016 to run for the U.S. Senate insists he could have done more in the aftermath of María – or at least been louder about it.

"Puerto Rico now suffers from the greatest discrimination in the entire country," Grayson says. "[I would have] fended off the discrimination. It's absurd. FEMA took four times as long to send any permanent aid to Puerto Rico as it took to send aid to Texas. What did [Soto] do about it? What did he do? As far as I know, nothing."

Grayson, 60, is challenging Soto, 40, in the Aug. 28 Democratic primary for the 9th Congressional District, which stretches from southeast Orlando to Kissimmee and St. Cloud, then south to Haines City, Winter Haven and Yeehaw Junction.

Although Grayson lives outside of the district, in Windermere, federal law only requires candidates to live in the same state. The winner will go on to face Republican Wayne Liebnitzky in the November election, but given the district's partisan lean, the victorious Democrat will almost certainly prevail. The Cook Political Report, for instance, does not rate this seat as competitive. In 2016, Hillary Clinton won the district by 13 points.

Of the district's nearly 833,000 residents, about 40 percent identify as Hispanic or Latino, according to 2016 data from the U.S. Census Bureau. And the district is rapidly changing. Puerto Ricans were already leaving the island for Central Florida in 2016 because of the financial crisis; María has only accelerated that exodus. That demographic shift would seem to favor Soto, the first Florida congressman of Puerto Rican descent.

Still, Grayson, a Jewish New Yorker, claims his internal polling (which he declined to share with Orlando Weekly) shows that he's ahead.

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Both men are seeking the mantle of "true progressive." Grayson famously rose to national prominence by telling Republicans in 2009 that their health care plan for the nation boiled down to "Don't get sick," and if you did, "Die quickly!" But on policy, the two are more alike than not, and both would almost always oppose Donald Trump. The real difference is that, unlike the lower-key Soto, Grayson will always crank his opposition to 11.

Another difference: their supporters. Or in Grayson's case, former supporters.

Democratic leaders, grass-roots activists and lawmakers across Central Florida have coalesced behind Soto. Quoting Shirley Chisholm, the first black woman elected to Congress, Grayson likes to say he's "unbought and unbossed," pointing to small-dollar donations from across the country that have funded his campaigns.

But over the years, the self-made millionaire has also alienated progressive allies in Central Florida. His run for Senate disintegrated after domestic abuse allegations. Some of his former supporters still remember his years in Congress fondly, but they wonder why he came back.

The campaign mudslinging has already begun, though it's mostly a one-way stream of attacks in Soto's direction: Grayson has called him "ineffective," "an elephant in donkey's clothing," "no Winston Churchill," and "boring," a lawmaker not willing to stand up to Trump.

Soto has kept his comments on Grayson brief: "He's rich and mean."

The feud between Grayson and Soto has been brewing since 2016, the year Grayson tried to make the jump to higher office.

The Harvard-educated lawyer, who made a career out of representing whistleblowers and his dogged prosecution of Iraq defense contractors who committed fraud, had first run unsuccessfully as an anti-war candidate for Congress in 2006. Two years later, he ran a more disciplined campaign, beating four-term Republican Ric Keller 52–48 in District 8, which spanned from Ocala to south Orlando.

Grayson's freshman term was marked by his outbursts – from brazenly attacking Republicans on their refusal to support Obamacare to taking Federal Reserve Chairman Ben Bernanke to the mat during a committee hearing while wearing a tie made of play money, which won him accolades from liberal activists. Sometimes, however, he was unable to restrain his worst impulses. During an appearance on The Alex Jones Show (yes, that Alex Jones), he called an adviser to Bernanke a "K Street whore." (He later apologized.) He lost his 2010 re-election campaign by 18 points after running an ad that called his opponent Daniel Webster "Taliban Dan," an allusion to Webster's conservative religious beliefs.

After redistricting created a safely blue seat in District 9, Grayson made his comeback, trouncing Republican Todd Long by 25 points in 2012 after accusing Long of being a domestic abuser, which Long's ex-wife later said was false. Back in Congress, he became an outspoken critic of President Obama's Syria policy. He also became adept at the art of legislating while in the minority. In interviews, Grayson never fails to mention that the online magazine Slate called him "The Most Effective Member of the House" in 2013 for his propensity to add amendments to bills, most appealing to the libertarian tendencies of his GOP colleagues.

But he never lost his bomb-throwing sensibilities. In 2013, for instance, he sent out an incendiary fundraising email likening the Tea Party to the Ku Klux Klan that featured an image of a burning cross. Grayson shrugged off the backlash: "If the hood fits, wear it."

His over-the-top rhetoric had the Democratic establishment terrified of Grayson's 2016 bid for the U.S. Senate. Party leaders rallied behind the moderate U.S. Rep. Patrick Murphy, a former Republican whom they deemed more electable and less embarrassing.

Grayson couldn't have cared less. Democrats, he boasted in 2015, are "willing to crawl over hot coals naked to vote for me."

They weren't. To say his 2016 run in the Democratic primary for Senate was marred by controversy is an understatement. It was a shitstorm.

First there was the New York Times report that alleged the anti-corporate hero ran a hedge fund in the Cayman Islands during his time in office, amassing millions. The Office of Congressional Ethics said in its report that there was "substantial reason to believe" several allegations of impropriety, including accusations that Grayson had a congressional staffer use official resources while working for the hedge fund. When a reporter asked him about the hedge fund, he shot back, "Are you some kind of shitting robot? You go around shitting on people?"

"I was exonerated," Grayson maintains. "They decided not to investigate because the charges didn't make any sense." (That's not quite true. The completion of Grayson's term in January 2017 ended the House Ethics Committee's jurisdiction over him before the committee finalized its review of the report's findings.)

Then there were the domestic violence allegations from Grayson's ex-wife and the mother of his five children, Lolita Grayson, who accused her former husband of threatening to kill her and abusing her over two decades, including four incidents in which police were called in Orange County and Virginia. In a 1999 report released to Politico, Lolita Grayson told police in Fairfax County, Va., that her husband had previously thrown her to the floor and hit her "on the back of the head with a large [object]."

Grayson has denied those accusations, instead accusing his ex-wife of "repeatedly" hitting him. "It's even ridiculous to talk about it," Grayson says. "My ex hit me twice in the face – you can find that on YouTube."

The 2014 video to which he's referring, shot by one of Grayson's former staffers, appears to show Lolita Grayson striking her husband in the face, which Grayson says contradicts a police report she later filed. In a statement at the time, the estranged couple's 18-year-old daughter said, "At no time did my father hit or push my mother."

Somehow, things only got worse.

Grayson got into a shoving match with the Politico reporter who initially reported on the domestic abuse allegations. Longtime national progressive allies dropped their endorsements. He got into an argument with then Senate Minority Leader Harry Reid at a Congressional Progressive Caucus meeting, in which Reid told Grayson that he has "no moral compass," accused him of being unethical and said, "I want you to lose." Political analysts considered Grayson's campaign dead in the water. And it was.

Murphy won the Democratic nomination going away. Grayson got just 17 percent of the vote. In November, Murphy was spanked by U.S. Sen. Marco Rubio, 52-44.

As his Senate bid was spiraling, Grayson was also running a shadow campaign in District 9.

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Soto, a former state senator, launched his campaign for the open congressional seat after spending almost a decade in the Florida Legislature. Born in New Jersey to an Italian-American mother and a Puerto Rican father, Soto moved to Orlando after getting a degree in economics from Rutgers University in 2000. After graduating with a law degree from George Washington University, Soto went into commercial law, though he did take up civil rights cases, including a 2006 federal class action suit against the city of Kissimmee by Latino voters. He joined the Orange County Young Democrats, a powerhouse group of progressives in Central Florida that helped elect former state Rep. Scott Randolph, currently the Orange County tax collector.

Soto made it to the Legislature in 2007 but got off to a rocky start. Though he was praised for his environmental record, progressives lambasted him for voting for abortion restrictions including mandatory ultrasounds and a 24-hour waiting period. He was given an "A" rating by the National Rifle Association and backed a 2011 bill that banned doctors from asking patients about their guns.

Soto says his positions have evolved. He's voted against abortion restrictions several times, helped lead efforts to defeat the 24-hour waiting period while in the state Senate and has been endorsed by Planned Parenthood. His opinions surrounding gun restrictions changed after the Newtown school shooting in 2012, he says.

"All my opponents will always bring up 10-year-old and 8-year-old votes," he says. "Voters know better. I've been endorsed by Planned Parenthood in my last five elections now. I regret votes that were 10 years and older. They aren't reflective of my opinions over the last decade."

Grayson's district director and former community organizer Susannah Randolph – Scott Randolph's wife – also decided to seek her boss' seat. But Grayson declined to support her, even though she was among his closest political allies. Their relationship went south, and Randolph left the office after learning Grayson wouldn't give his blessing.

As it turns out, Grayson already had someone in mind, and it was neither Soto nor Randolph. It was his girlfriend, Dena Minning.

Grayson married Minning – a medical doctor and federal lobbyist representing a pharmaceutical company – a few months before the election, giving her enough time to change her name to Dena Grayson on campaign materials and the ballot.

"She's going to have my name, and I'm going to spend a lot of money on television," Grayson said of his new wife, U.S. Rep. Lois Frankel told Politico at the time.

But Grayson's name wasn't enough. Randolph and Dena Grayson split votes in Polk and Orange counties, leading to Soto's victory in the four-way primary with 36 percent support. Soto went on to handily win the general election.

The Grayson machine, though, never sleeps.

Two days after Election Day in 2016, he got a $400 contribution toward his next campaign and continued raking in cash over the next year. Months after Donald Trump was sworn in, Grayson launched lockhimupnow.org, which asks for donations to The Resistance PAC. It's not clear how much of the money has been spent on "resisting" the Trump administration (however vague that term might be), but federal records show the almost $52,600 from the political action committee has gone to consulting services, a voter data mining company and about $4,000 to one current Grayson campaign staffer.

Pat Schroeder says she doesn't know where Alan Grayson went wrong.

The first woman to represent the state of Colorado in the U.S. House was a champion in Grayson's corner year after year during his re-election bids, partially because of his stances on reproductive rights. In a video from 2010, the Celebration resident said she was "lucky enough to have Alan Grayson as my congressman. And believe me, what a delight he is."

But in 2016, Schroeder and other local women leaders endorsed Randolph. She's not sure when it happened, but her relationship with Grayson deteriorated, now to the point where Schroeder has accused Grayson of hiring protesters to show up at Soto's rallies – including one event where a protester held a sign calling U.S. Rep. Lois Frankel "senile."

Grayson calls the allegations of fake protesters "irresponsible" and "baseless."

"I'm very sad that Grayson is doing this," Schroeder says. "I wish he would run in some other district that he could flip. I don't know why he's doing this."

Schroeder is one of several former Grayson supporters in Central Florida who can't fathom why Grayson would challenge a sitting Democrat – though, privately, they suggest that it's about his considerable ego than anything else.

Schroeder and former Orange County Chair Linda Chapin were attending a "Women for Soto" event in June where Frankel was speaking. Like the other nine Florida Democratic members of Congress, Frankel has endorsed Soto's re-election. Beyond the crowd, Schroeder says she and Chapin saw a group of young people with a sign that read, "Lois Frankel: Still Senile."

"We were shocked," Chapin says. "We were amazed that someone would take that extreme a measure just to try and discredit Frankel. Lois had come from South Florida just to support Darren."

Soto says one of his campaign staffers approached the protesters, who told the staffer they were "paid $500 by Grayson to carry these signs and they go where the money is." Previously, protesters had shown up at another of Soto's rallies, this time with signs calling him an "NRA sellout" and saying he was "willing to cut Social Security."

Calling Frankel an "icon in the fight for women's equality in Florida and the nation," Schroeder and Chapin sent a letter to the Democratic National Committee and the Democratic Congressional Campaign Committee asking for them to investigate Grayson.

"It's an ugly kind of thing to do to a supporter of an opponent," Chapin says. "Frankel used to be a colleague of Alan Grayson in Congress. They served together. I can't imagine what's going on in his head. All the people who used to support Alan before used to think he was pretty edgy, he was smart and funny, but I think people just can't reconcile what he's doing now with the kind of person they thought he was."

Grayson says there's nothing in his financial reports that indicates he paid anyone to protest.

"It's a pathetic effort by the Soto campaign to try to distract people," he says.

It's not clear what Soto would want to distract people from.

After all, the coalition of progressive groups – including seniors, African Americans, Latinos, union members and the LGBTQ community – that previously propelled Grayson to victory have all but abandoned him. The incumbent has also received high-profile endorsements from figures like former Vice President Joe Biden and U.S. Rep. John Lewis, a civil rights legend.

Soto may not have Grayson's national presence, but neither does he have his baggage. And in office, he's developed a reputation as a workhorse for his constituents.

"Soto works better," says Fernando Negrón, host of the left-leaning political radio show "Quédate con Miguel" in Orlando, who previously supported Grayson. "Grayson is more about grandstanding, being on CNN, MSNBC, Fox News, which I like. But I want a guy that does something, not just a loudmouth."

Grayson, though, sees cracks in Soto's armor. He points out that Soto lost the 2016 primary in Polk County.

"Polk Democrats are more liberal than Orange County Democrats," Grayson says. "In Polk County, the Anglo vote is a liberal vote, and in many cases a union vote, so the teachers weren't happy with Darren's support for charter schools. I think that both the white vote and the black vote in Polk were very unhappy with Darren's record on guns."

However, several African American public officials in Polk County are supporting Soto, including Winter Haven Commissioner Nat Birdsong, Lake Wales Mayor Eugene Fultz and prominent Winter Haven community activist Twanna Dewdney. Ruth Ann Eaddy, a Lake Hamilton resident, says Soto has provided more constituent services to the area than Grayson ever did, including securing money for new police cars and nearby fire departments.

"I think [Grayson] is just doing it for spite because Darren beat his wife," Eaddy says. "Darren has been able to work in the state Senate and House when it's been all Republicans and has been effective. He can work across the aisle and he knows how to find common good. He's not a loudmouth. He's very humble and he just does his job."

Keith Laytham, an advocate who works with the resident group Friends of Poinciana Villages, says Soto was instrumental in procuring $11.9 million to open a Valencia College campus in Poinciana and fought to obtain funds for the Poinciana Parkway.

"He pays attention to the needs of the people," Laytham says. "From a political standpoint, a lot of the things Grayson says I find to be attractive, but it's a big disappointment to me that he chose to run against Darren Soto. Why didn't he choose to take on some of the Republicans? Why did he have to go after a Democrat doing a good job?"

Asked that question, Grayson campaign manager Brook Hines says District 9 is where the former congressman can win. "Alan is running to win," she says. "He's not running for vanity."

Hines, who served as Grayson's deputy communications director during his Senate campaign, says she's been a Grayson fan for a while because he's been one of the most successful small-donor fundraisers in Congress. He's always run on a progressive platform. Aside from being an effective legislator who led efforts to audit the Federal Reserve, Hines says Grayson was also successful at bringing money home, including getting funds for the Orlando VA Medical Center.

"He's unbought and unbossed," she says. "That's one of the things for me that's wrong with the way our electoral system is working right now. There's too much special interest money. Even really good people, good Democrats can get caught up in that contributor/donor cycle of taking corporate money and serving special interests instead of real people."

Grayson has so far raised more than $500,000 from individual contributions since January 2017, leaving him with nearly $700,000 in cash on hand as of the end of March, according to campaign finance reports. Most of the contributions – about $421,000 – were in increments of $200 or less. More of Grayson's funding, though, is coming from California ($70,482) and New York ($49,123) than Florida ($38,834).

In the same period, Soto raised nearly $571,000 and has $364,000 on hand. Most of his money came from large individual contributions and PACs, including $7,500 from American Crystal Sugar and $2,000 from NextEra Energy, a utility company whose subsidiaries include Florida Power & Light. Most of Soto's contributions, though, are from Florida ($138,377) and Puerto Rico ($31,800).

Soto's detractors have long criticized his contributions from sugar and utility companies. And Grayson has slammed Soto for taking money from charter school proponents, including $230,000 from a Texas billionaire during the 2016 primary.

"If you look at Darren's FEC reports, you see a troubling pattern," Grayson says. "He's simply bought and paid for."

Hines says Soto has also shown he's "clumsy," referring specifically to a statement he made in January, when he instructed Puerto Rican evacuees to tell federal authorities they intended to stay in Florida, whether they planned to or not, to access medical benefits. Doing so could be interpreted as lying on a government form, which is illegal.

"Many recently arrived Puerto Ricans have a high probability of staying in Florida," Soto told WFTV. "The intent of my statement was to encourage them to err on the side of caution and declare their intent to stay if they are in doubt about their future plans."

Jeremy Fetzer, of the group Osceola County Brass Tax, told WFTV that he filed a complaint with the Congressional Ethics Committee about Soto's remark, though the ethics committee would not confirm whether an investigation was taking place. (According to its Facebook page, Brass Tax "is dedicated to getting the word out on issues facing our County, State and Country thru the collective of our community." Its photo section is full of pro-Trump memes.) Still, Soto's statement has served as fodder for the Grayson campaign's effort to discredit Soto's efforts to help displaced Puerto Rican families.

"If you're going to represent people and going to support them, leadership requires more than just strongly worded letters," Hines says. "Darren's trying to fill a very big boot, and he just hasn't quite yet – it's still a bit large on him. For me, it's about wanting a congressman who knows how to get things done, who's just a bulldog and going out there to make things happen."

But Jimmy Torres-Vélez – a former labor organizer who was a finalist for the Orlando Sentinel's Central Floridian of the Year award for his aid to Puerto Rico after the hurricane – says Grayson was nowhere to be seen when he and others were collecting donations for the island.

"I didn't see Grayson in any of the warehouses," he says. "He didn't organize trips to Puerto Rico. He hasn't been with the families displaced from Puerto Rico. So why is he claiming he wants to do anything? He says he's a gutsy guy – well then, go and challenge one of the Republicans all over Florida who are doing very bad things to this state."

Just under the surface, there have been vague accusations of "identity politics" in this heavily Hispanic district. In an interview with the Orlando Sentinel, Grayson said Soto wanted to "make this about someone who claims Puerto Rican heritage, by virtue of the fact his father was born [there] and he left as a small child, versus an Anglo from New York."

"I view him saying that as the highest compliment," Soto says, "because that just shows he can't communicate with those groups in an effective way. And they're scared."

If Grayson is scared, he'd never admit it. To do so would run counter his very nature. Since he stepped onto the political stage, Grayson has oozed confidence and self-assurance, often to the point of condescension, and has quite obviously held his political rivals in contempt. Darren Soto is no exception.

As is Grayson's wont – and might be well-suited to the age of Trump – the challenger has lobbed plenty of pointed jabs at the incumbent during the campaign. In the first few paragraphs of a June fundraising email, for instance, he called one of Soto's speeches "flat," "boring," and "a simple desultory philippic." (Philippic is a 10-dollar word for "tirade.") In a more recent fundraising message, he called Soto a "bootlicking lackey to the NRA," "professional poseur" and "whiny."

"We're talking about the issues that matter to people," Soto says. "We're talking in positive terms. The mudslinging is only going one way."

Indeed, this race is much more about style than substance. Both men have come out strongly against Trump policies. Grayson just does it more belligerently.

"I'm one of the few people running for office this year who has the courage to come out and say Donald Trump should be impeached and convicted and removed from office," he says.

Soto says he'd vote for impeachment after the Russia investigation wraps up. Grayson, who has paid to put up a billboard in Polk County calling for people to "DUMP TRUMP," says there's no reason to withhold judgment.

"I think there's already ample evidence that this is worse than Watergate," he says. "We've already reached the threshold where the president should be impeached. It's a dereliction of duty to wait any longer than that."

Soto argues that he's stood up to Trump when it's productive, not just to "make more copy in the newspaper."

"We have called Trump out multiple times for his underfunding of the disaster, for the death count, for so many other things," Soto says. "But most of this productive work that gets done is through Congress and through FEMA.

"Foaming at the mouth and standing on your desk will produce little additional results."

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