In his bid for Senate in Florida, the biggest thing standing in Democratic Rep. Alan Grayson’s way is … Alan Grayson.

The three-term Orlando lawmaker is a hero among progressives for his stances on health care policy and regulating Wall Street — something that makes him a seemingly formidable candidate in a Democratic primary. But as he looks to secure his party’s nomination in a statewide bid, his unfiltered remarks and the circus that surrounds his private life threaten to derail his statewide ambitions before primary day.

“He can’t get out of his own way,” said Ana Cruz, a Tampa-based Democratic consultant.

At first glance, Grayson appears to be the front-runner for the Senate seat left vacant by GOP Sen. Marco Rubio’s presidential bid.

A Harvard-educated lawyer with a rags-to-riches story — the lawmaker paid his way through college by working as a night watchman and janitor — Grayson rose to prominence with his bombastic statements during the health care overhaul debate in 2009.

Since announcing his Senate bid last month, Grayson’s led in a handful of early polls thanks to his familiarity to voters in the Sunshine State. And both his national fundraising base and his immense personal fortune (Grayson was the 17th richest member of Congress in 2014, with a net worth of at least $26.18 million, according to a CQ Roll Call analysis.) will give him the resources statewide hopefuls dreams of.

Yet Grayson’s campaign launch has been marred by missteps and negative press.

First there was the revelation of Grayson’s involvement in three hedge funds, two of which are based in the Cayman Islands, that bear his name. It’s the type of activity Grayson has decried since he was sworn in to Congress in 2009.

Grayson’s campaign denies any wrongdoing, but Florida Democrats say it’s an issue that could hurt Grayson even among his most fervent progressive followers.

“I think that thing is not going to go away,” said one Florida Democratic consultant. “It’s just going to always keep needling him, and that’s so far the hardest thing for his supporters to rationalize and explain away.”

There’s also Grayson’s girlfriend, Dena Minning, a biotechnology entrepreneur who announced a bid for the 9th District seat Grayson is vacating to run for Senate.

Minning’s candidacy could serve as a distraction for Grayson’s Senate hopes, and keep relevant a nasty and public divorce Grayson endured over the past year. Grayson eventually annulled his marriage of 25 years with his ex, Lolita Grayson, but not before round after round of public name calling and negative news stories — including one report that Lolita and the couple’s children were allegedly on food stamps, despite his wealth.

Minning’s candidacy has also frustrated some of Grayson’s most loyal allies in his district, many of whom are supporting Susannah Randolph — Grayson’s former district director and political adviser who has close ties to the grass-roots progressive activists in Orlando.

“I don’t think it’s helpful to your U.S. Senate race to have your girlfriend running for your seat,” said John Morgan, a Florida Democratic donor and friend of Grayson’s, who supported Grayson in the House but advised him against a Senate bid. “But when it comes to male and female attraction, even a Harvard-educated lawyer doesn’t see what the rest of us see.”

Grayson declined to comment to CQ Roll Call last week when asked about whether Minning’s candidacy could be problematic for his own Senate hopes, and instead referred to a statement his campaign issued when Minning announced her bid in July. In the statement, Grayson praised Minning’s support for universal health care, but said he would not be making an endorsement “at this time.”

Even more, Democratic operatives say the same outspoken remarks Grayson became famous for could end up hurting him in a statewide contest.

In 2009, Grayson said Republicans’ plan for overhauling the country’s health care system was to “die quickly.” In his 2010 re-election campaign, Grayson called his opponent, GOP Rep. Daniel Webster, “Taliban Dan.” Grayson also sent out a fundraising email in 2013 comparing the tea party to the the Ku Klux Klan.

Democratic operatives compare Grayson with businessman and Republican presidential hopeful Donald Trump — who is being rewarded by voters in the polls for his candid remarks, but whose penchant to speak whatever’s on his mind often lands him with a flurry of negative media attention.

Still, Democrats who support Grayson’s opponent, fellow Democratic Rep. Patrick Murphy, say Grayson won’t go quietly.

Grayson has already begun to attack Murphy — who came to Congress in 2012 when he defeated tea party firebrand and now former Rep. Allen B. West — as too moderate.

And while they think Grayson won’t end up being the nominee, Democrats in both Florida and Washington say it’s going to be an expensive fight the party would have rather avoided in this Tossup contest key to Democrats’ hopes at a Senate majority in 2016.

“It’s sub-optimal, we hoped to avoid him, but I don’t think anyone is panicking,” the Florida Democratic consultant said. “But if anyone can take on a fringe person named Alan, it’s Patrick Murphy.”

Correction 6:39 p.m.

An earlier version of this post misstated the locations of Grayson’s hedge funds. Only two of the three mentioned are offshore.

Related:

GOP Gleeful That Grayson’s Getting Into Florida Senate Race

Grayson Email May Run Afoul of House Ethics Rules

Alan Grayson to Announce Senate Bid Thursday

Roll Call Race Ratings Map: Ratings for Every House and Senate Race in 2016

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