Central Florida’s fiery Democratic Congressman Alan Grayson wants to wage a campaign for the U.S. Senate based on economic populism and income disparity. But observers say the key to his success will be whether he can control his penchant for outrageous—and sometimes distracting—outbursts.

Grayson announced his candidacy this morning from Washington in a low-key, almost mellow interview with an Orlando TV station. The three-term congressman made clear his slogan for the Democratic base could well be: “If you like Elizabeth Warren, you’ll love Alan Grayson.” In a July 3 email, Grayson asked supporters who wanted him to “join Elizabeth Warren and other good Progressive Democrats in the Senate” to vote with their checkbooks in the next 24 hours, and they did, contributing $110,000, which later rose to $133,000.

“We’re going to be running an Elizabeth Warren-type campaign,” he told me in a telephone interview this afternoon, “and I think that Elizabeth deserves more support in the Senate for what she’s trying to accomplish. For me, the way to do that is to run as an unapologetic progressive.”

While Grayson may share many positions—and a Harvard connection—with the Massachusetts senator, their personalities are polar opposites. And yet, unlikely as it sounds, there is actually a chance that this unabashedly left-wing, loud-mouthed, Bronx-born son of two Jewish, teachers’ union members may replace Marco Rubio in the U.S. Senate. In the process, Grayson could tip the Senate majority back to the Democrats and become Florida’s first Jewish senator since Richard Stone, another New York native who grew up in Miami and who served one term in the 1970s.

There was also a Jewish senator in antebellum times, David (Levy) Yulee, after whom one Florida county and one city are named. Yulee was as outspoken in his time as Grayson is today, although the two were opposites. Yulee was a defender of slavery before the Civil War, and of white supremacy after. “Judaism offers timeless principles,” Grayson said, “but different people have found different meanings at different times. In my case, the religious principle tikkun olam inspires my work.”

Grayson estimates that the Democratic primary will cost him $5 million-$10 million, and the general election up to $25 million more. Some of this may come from his personal fortune, but the bulk is expected to come from his donor base of 100,000 small contributors. If his campaign strategists have their way, Grayson’s approach in the upcoming Senate run may be less hard-edged and bombastic, distancing himself from his wild-man image. Given the Sunshine State’s distinctive Democratic mosaic, Grayson’s approach could work, at least in the Democratic primary, as he told a local Fox TV affiliate. “I have the Hispanic vote,” he said. “I have the black vote. I have the Jewish vote. I have the labor vote. I have the vote of liberals all around the state. These are the pillars of the Democratic Party.” He also has strong backing from the gay community—he served as a ring bearer at a mass gay wedding on the steps of the Osceola County Courthouse last January—and seniors, who are a significant constituency in the state.

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Florida’s August 2016 Democratic senatorial primary will also be a bellwether battle—in a critical swing state—between the Democrats’ progressive and centrist wings. In the primary, Grayson, 57, will face Rep. Patrick Murphy, of Palm Beach, a former Republican who has emerged as the preferred candidate of establishment Democrats and Wall Street donors. In a June 22, Quinnipiac University poll, which echoed three earlier polls, Grayson and Murphy were within the margin of error in matchups with the three most likely GOP candidates. A Gravis Marketing poll of 881 registered Democrats, released July 2, found Grayson well ahead of Murphy. However, Peter Brown, assistant director of the Quinnipiac Poll who handles Florida surveys, urged caution at this early date. “The vast, vast majority of Floridians and the vast majority of primary voters outside Central Florida don’t have a clear picture of who Alan Grayson is and what he represents,” Brown told Tablet. Early in May, the Democratic Senate Campaign Committee endorsed Murphy over Grayson, saying that Murphy is more electable.

Grayson is confident, rejecting the notion that he is too liberal, or too Jewish, or too much of a Northeastern outsider to be elected statewide. “There is no ‘typical Floridian,’ ” he said, during a lengthy interview in Orlando, several weeks before his announcement. “That person doesn’t exist. If it’s possible to find a way to win, I will find a way to win. The real questions are, ‘How do I win? How do I get things done? How do I show that a Democrat can change the law and make the world a better place?’ Democrats want an action figure from among their elected officials.”

If Grayson wins the primary, the general election will be an even tougher sell—but again, not impossible. While it has had two, two-term, Republican governors (Rick Scott succeeded Jeb Bush) and a GOP-controlled legislature, it has gone twice for Barack Obama and, arguably, once for Al Gore. Two Republicans have entered the senatorial race, Jacksonville Congressman Ron DeSantis, backed by the Tea Party, and Lt. Gov. Carlos Lopez-Cantera, a Cuban American. Stronger Republicans have stayed out of the race, concerned that if Marco Rubio’s presidential campaign collapses, he will reenter the race.

‘Whether Jews will support Alan Grayson’s bid for the Senate is a great test for how Jews in Florida balance their politics and their religious identities.’

There are several question marks for Grayson in the upcoming race. Chief among them is the charge that in 2011, while out of office, Grayson set up a number of personal hedge funds in the Cayman Islands. When a Tampa reporter asked Grayson about it, the journalist was subjected to a stream of curses, later explaining that the funds were never used. However, citing the Cayman Islands funds, and the two complaints recently filed with the Office of Congressional Ethics, liberal Democratic state Senator Eleanor Sobel of Broward County said on July 7 that Grayson was “embarrassing my party and my state,” and so was endorsing Murphy. Another is what impact, if any, the recent, acrimonious breakup of his second marriage will have. Charges and counter charges filled the local newspaper and blogosphere, but nothing so far has stuck to Grayson, except his reference to his estranged wife, who is not Jewish, as a “gold digger.”

Yet for all his disheveled bluster, Grayson is a canny, strategic thinker, planning many moves ahead, like the high-school chess-club veteran he is. A Bronx High School of Science graduate, Grayson worked to pay his way through Harvard, earning a bachelor’s degree in economics, a master’s degree in public policy, and a law degree. In the ensuing decades, he made three small fortunes—today estimated at about $30 million—in telecom, in the stock market, and by suing profiteering defense contractors on behalf of whistleblowers during the Iraq War. The latter led to favorable profiles in Vanity Fair and the Wall Street Journal and gave him the idea of entering politics in Orlando, where he moved in 1996.

In his first run for Congress in 2006, he lost in the primary to a traditional, moderate Democrat, firmly rooted in the community. Grayson came back in 2008 with a vigorous anti-Iraq war, anti-corporate campaign in the swing district. He largely self-financed that winning effort with personal checks and loans for $2.62 million of the $3.2 million spent on the campaign.

In his first term in Congress, Grayson was the perfect example of the adage that, in politics, timing is everything. On Sept. 29, 2009, when the Democrats were most frustrated in the fight over President Obama’s Affordable Care Act drive, the six-feet-four Grayson shambled into the well of the largely empty House floor. Standing next to an easel holding a series of posters, he angrily proclaimed: “If you get sick, America, the Republican health-care plan is this: Die quickly! That’s right. The Republicans want you to die quickly if you get sick.”

The ensuing notoriety, followed by similarly sharp-edged comments—comparing Dick Cheney to a vampire who turns into a bat, and describing a female K Street lobbyist as a whore—made him an instant champion of the Democratic base. Like supporters of Grover Cleveland, they loved him for the enemies he made. One of Grayson’s favorite lyrics, he told me in a 2009 interview in his Capitol Hill office, was from a Billy Joel song: “I just may be the lunatic you’re looking for.” More seriously, he says his lifelong commitment to helping the poor and the powerless is rooted in Jewish ethos and tradition.

Back in Central Florida, some were scratching their heads, thinking that this national notoriety was a double-edged sword, making Grayson a prime target of the conservatives like the Koch brothers and Karl Rove.

“I thought he was becoming so outrageous it would not help him get reelected,” recalled Aubrey Jewett, professor of political science at the University of Central Florida. “It was not a good campaign strategy. It was just him being him.”

Sure enough, in 2010, Grayson was unseated in the Tea Party surge. Although pronounced politically dead by right-wing radio hosts, he came roaring back in 2012. Running in a redrawn, largely Hispanic and Democratic district next to his old one, he won by an unprecedented marginal swing. In that race, his Anglo Republican opponent said he was “the most anti-Christian congressman probably we’ve ever had in our history.” But, in a departure from his previous firebrand rhetoric, Grayson didn’t rise to such baiting in 2012.

Returning to a House under Republican control Grayson racked up an enviable record—noted by Slate and Time magazine—of maneuvering more than 30 amendments to passage on the House floor, all the while, he claims, relying on guile rather than compromise. But to constituents back home, it appeared that a new, more pragmatic Alan Grayson was emerging.

“He is capable of learning,” said UCF’s Jewett. “He doesn’t like to admit that he makes mistakes, but he learns from them.”

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One problem for progressive Democrats—nationally, in Florida and on Capitol Hill—is that Grayson has a way of rubbing people the wrong way. While they agree with almost all of his positions, domestically and internationally, they can’t stand him, although no one will say so on the record. “There is no love lost for him personally or politically in our office,” said one liberal lobbyist.

It is also hard to tell to what degree Grayson’s Jewishness may factor into the race. Grayson says his original, Jewish family name—which he won’t disclose—was changed in an earlier generation. He went to Hebrew school, observed the Jewish holidays, and had a bar mitzvah. On the Judaism spectrum, he now puts himself about midway between secular and observant, but he did send his children to a local Chabad school. In his campaigns, he neither hides nor emphasizes his heritage, except when meeting with Jewish groups and donors. One 2014 campaign event was even held on Rosh Hashanah.

“Unlike Sandy Koufax,” he said, over a lunch that included bacon, “I feel like I sometimes have to bend the religious rules a little in order to do my job properly and meet my responsibilities to the general public.”

Israel was always part of his family’s conversations in the Bronx, and one set of grandparents were ardent Zionists. In his three terms in Congress, Grayson has been one of those Jewish Democrats who is strongly, consistently—even flamboyantly—liberal on most everything but Israel. A member of the House Foreign Affairs Committee, he didn’t boycott Prime Minister Benjamin Netanyahu’s controversial speech last year to a joint session of Congress. While he parted company with AIPAC on U.S. intervention in the Syrian civil war, he returned to the fold to oppose the proposed Iran nuclear agreement.

“I’m concerned [the agreement] is not going to be comprehensive enough—if there is a deal,” he said in the telephone interview Thursday. “Rather than a pause in their nuclear program I would want to see it eliminated. Also, there’s been no discussion at all about Iran’s intercontinental ballistic missile program. And it leaves the Iranians with no real pressure regarding their support for terrorism in the Middle East.”

In particular, he questioned the proposed $150 billion “signing bonus” for Iran, saying there is no way to ensure the funds won’t be used to support global terror and the Assad regime.

Grayson is also troubled by the suggestion that the United States should be fighting ISIS in Iraq alongside Iran. “It’s a Sunni Arab problem, and there should be a Sunni Arab solution. I would support an international force that doesn’t include U.S. troops. It needs to be Muslim forces fighting back against Muslim extremists. U.S. intervention would only further inflame the sectarian divisions within Iraq and also within Syria.”

He is adamantly opposed to opening a dialogue with Hezbollah, Hamas, or the Muslim Brotherhood, although he doesn’t think it is necessary to provide any additional aid to the Al-Sisi regime.

Grayson’s trip to Israel in early May, sponsored by an AIPAC-affiliated group, was his third. This time, with other lawmakers, Grayson met with Netanyahu and President Reuven Rivlin, visited Yad Vashem, and was briefed by IDF officers at military headquarters. He also met with Palestinian Authority leaders.

Over the years, whenever I questioned him about his unwavering support for specific Israeli government policies, he seemed uncomfortable and brushed me off. The question of settlements, Grayson says, is “a loaded one,” and he refuses to say that they damage the efforts to find a two-state solution, which he says he supports.

If Grayson is supported by AIPAC members in his senate run—the organization does not make candidate endorsements—it remains to be seen whether he will also get support from  progressive Jewish groups. The new, more liberal Bend the Arc PAC, supported by Alex Soros, makes its endorsement solely on the basis of domestic positions. It tends to steer clear of contentious primaries like the one expected in Florida. Should Grayson win the Florida primary and make it to the general election, “We would have to dig into his record,” said Hadar Susskind, Bend the Arc’s director. “But it’s likely that he fits our issue profile pretty well.”

About 10 percent of Florida’s Democratic primary voters are Jewish. Most of them—and the strongest Israel backers—are in South Florida, where Grayson is little-known, so his AIPAC ties may help there. In the general election, 3 percent to 6 percent of the state’s voters are Jewish, about 500,000. Grayson has been a constant media presence in the area around his congressional district, which is largely Hispanic, African American, and working class. Yet this may not have helped him among middle-of-the-road Jewish voters, who may disagree with his more leftist positions and find his bombastic style distasteful. When asked their opinion of Grayson, what seems to be on the tip of these tongues is the old Yiddish expression, “shanda fur die goyim,” an embarrassment in front of the gentiles.

“Grayson will lose some of the Jewish vote from those who don’t care for his arrogance and overbearing personality,” said Rabbi Steven Engel, of Orlando’s Congregation of Reform Judaism. “They will cringe at this as only reinforcing a bad stereotype of a Jew, rather than a serious candidate for the Senate.”

Even among some single-issue, “Israel-first” voters, the unofficial AIPAC imprimatur may not be enough.

“The position on Israel for most candidates is not going to be the determining factor for how Jews vote,” Ira Sheshkin, director of the Jewish Demography Project at the University of Miami, recently told the Tampa Bay Times. “Jews vote on social issues.”

And on economic issues, especially Jewish doctors angry at Grayson’s energetic support for Obamacare.

“When I cast my vote, I consider multiple factors,” said Dr. Stan Sujka, a strong Israel supporter, and a registered Republican, who lives in Winter Park, a tony suburb outside Orlando. “Israel is a very important issue for me, but it’s not the only issue to evaluate a candidate. Domestic issues are much more important, since I feel that only a strong America can help to guarantee a strong Israel. Mr. Grayson has a lot of negative factors associated with him and that one positive factor of being a supporter of Israel, is not enough to sway my vote.”

But this could also redound to Grayson’s benefit.

“As a liberal Jewish voter, uncomfortable with AIPAC and Likud, I’d still back him because of his liberal views,” said Cathy Lieblich, a social worker and liberal Democratic activist. “That is, if I didn’t like the alternative and I thought he could win the general election.”

“Whether Jews will support Alan Grayson’s bid for the Senate is a great test for how Jews in Florida balance their politics and their religious identities,” said Rabbi Engel, who also hosts a weekly interfaith show on public radio. “Their Jewish side will certainly like him for his support of Israel and his liberal position on social issues. However hawkish his Israel position is, I think this will be forgiven given his liberal domestic agenda. As far as their political side is concerned, Grayson will lose that part of the Jewish community that will not support a liberal candidate, no matter what his position on Israel might be.”

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