Rick Brand is a longtime Newsday reporter who writes about politics and government on Long Island.
Call them the rebound boys.
His opponent is party newcomer Doug Segall, a Democrat only since 2008 who, despite the backing of former County Executive Robert Gaffney and state Sen. Kenneth LaValle, was trounced a decade ago in a bid to become the town's GOP chairman.
Political insiders say Alessi, 34, has the edge for the unpaid party job because of his decade of experience in Albany and as a political operative for major Democrats, among them Hillary Rodham Clinton and former State Comptroller H. Carl McCall along with the Civil Service Employees Association.
Segall disputes that assessment though, ironically, the two are friends. Segall spent Election Day driving Alessi door-to-door in a final campaign blitz.
Alessi, who announced his bid three weeks ago, said he has called all 220 party committee members in Brookhaven - and has the backing of Suffolk Democratic chairman Richard Schaffer and encouragement from Town Supervisor Mark Lesko. "Before I was elected I ran campaigns for 10 years," said Alessi, of Shoreham, a lawyer with the Nassau firm of Jaspan Schlesinger. "I have the organizational skills and have built up a Rolodex that can help build the party and raise funds."
Segall, 53, of Farmingville, has been campaigning since December. He's already sent out three mailings and held a reception at this home Jan. 2 for party committee members. Backers include Brookhaven Town Board member Connie Kepert and Town Clerk Patricia Eddington.
"I was the first one out of the box . . . and I've proved I can get the committee energized and involved," said Segall, vice president of Perception Imaging, which does direct mail work for Democrats. Segall said he's worked more years as a political operative than Alessi and that he has "a longer history in the business community and a different skill set for raising money."
GOP once dominated
The new leader's job will be to solidify Democratic gains in the town, which Republicans dominated for decades. He'll face thorny issues including redistricting of town board lines, infighting among Democratic officials and Lesko's alliance with GOP town board member Kathy Walsh.
Brookhaven also will be a key battleground in the upcoming legislative and county executive races.
Some party veterans raise concerns about Segall's late conversion in 2008 and the conflict that could arise from his firm's printing work for the party.
Others worry that Alessi's recent loss could tar the party and that his young family and work for a Garden City-based law firm may cut into the time he can spend as leader.
Jesse Garcia, Brookhaven Republican chairman, said it doesn't matter whom Democrats pick "because we defeated both of them," and town voters have turned back to Republicans.
But Schaffer said Alessi's experience as an operative and lawmaker make him perfect for the town post. "He's a low-maintenance guy and he knows how to deal with the drama," said Schaffer. "And because of his age I think he will be able to attract more young people to the committee . . . He reminds me a lot of myself."
Despite his defeat in November, Alessi said, "Republicans may rue the day that [they] stopped my being a policymaker and made me a political leader."
Segall says he sees no animosity in the contest. "No matter what happens the party will wind up with a top-notch leader," he said.