As supporters and critics traveled from near and far Wednesday to bid adieu to U.S. Sen. Joseph Lieberman, the question loomed: Could he have won re-election in 2012?

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We won’t find out. The four-term senator announced Wednesday, as expected, that he won’t run for re-election.

That doesn’t stop people from speculating about his reelection prospects—people, including Lieberman himself.

Surrounded by his family as he took the stage at the Stamford Marriott, Lieberman was greeted warmly by the crowd of supporters, many of whom worked on his campaigns and others were those with whom he has consulted over the past few months in trying to reach his decision to retire in two years.

Matthew Hennessy, managing director of Tremont Public Advisors, said the senator has been weighing his options about whether to run and whether he could win if he ran as an Independent.

“There was definitely a path to victory, ” Hennessy said Wednesday. “But the bigger question was, did he want to campaign for two years to win another six, or did he want to make the most of the next two years?”

Lieberman addressed the issue head-on in a 20-minute speech.

“I know that some people have said that if I ran for re-election, it would be a difficult campaign for me. But what else is new?” Lieberman joked.

“I’ve never shied from a good fight and I never will,” he said. “The reason I have decided not to run for re-election in 2012 is best expressed in the wise words from Ecclesiastes: “To everything there is a season, and a time to every purpose under Heaven.”  At the end of this term, I will have served 24 years in the U.S. Senate and 40 years in elective office. By my count, I have run at least 15 full-fledged political campaigns in Connecticut.

“For me, it is time for another season and another purpose under Heaven,” he said completing the reference to scripture.

Hennessy said the “don’t ask, don’t tell” victory proved to Lieberman that he can still get things done. Lieberman led the charge to repeal the military’s policy preventing openly gay and lesbian soldiers from serving.

The event Wednesday also drew Lieberman critics—including people who worked hard to unseat him in 2006 by supporting Democratic candidate Ned Lamont. Lamont defeated Lieberman in a party primary, but Lieberman kept the seat by winning the general election as an independent. The tough fight has left him smarting ever since.

Al Robinson, who blogged under the name “CT Blogger” in support of Lamont and in opposition to Lieberman, was in the back of the room Wednesday.

“If it wasn’t for Ned Lamont, we wouldn’t have this,” Robinson said. “We forced him to run as an Independent. But what he did after the election proved he was not the progressive he claimed to be.”

Robinson said it was worth the trip to Stamford to watch Lieberman announce his retirement. He said Lamont deserves some credit for Lieberman’s announcement Wednesday.

When Lamont won the Democratic primary in 2006, it forced Lieberman to run as an Independent. But that became a position Lieberman later embraced going as far as supporting Republican Senator John McCain in the 2008 presidential contest. The move seemed to be the last nail in the coffin for Democrats in Connecticut.

“Along the way, I have not always fit comfortably into conventional political boxes—Democrat or Republican, liberal or conservative,” Lieberman said in his speech Wednesday. “I have always thought that my first responsibility is not to serve a political party but to serve my constituents, my state, and my country, and then to work across party lines to make sure good things get done for them. Whatever the partisan or policy differences that divide us, they are much less important than the shared values and dreams that unite us and that require us to work together to make progress for all.”

But being an Independent-minded Senator hasn’t always been easy for Lieberman, who did not relish the idea of putting his family through another campaign. Unlike in 2006, he doidn’t stand to have Connecticut Republicans united behind him in 2012. He also, according to polls, had lost the support of many Democrats who voted for him in 2006.

Dan Gerstein, his campaign advisor in 2006, attended Wednesday’s announcement.

Gerstein said he understands that Lieberman may have alienated some Democrats over the years and he “paid a political price for his independence.”  It wasn’t the prospect of a tough campaign or the chance he could lose, but “2006 was a grueling experience,” Gerstein said, adding that with 10 young grandchildren and the 11th on the way, it wasn’t something Lieberman wanted to do.

“I take him at his word when he the prospect of being in a tough campaign and potentially losing was not the ultimate deciding factor,” Gerstein said.

Some veteran political figures in the state such as AFL-CIO Chairman John Olsen and New Haven Republican Chris DePino said they came Wednesday to pay their respects to Lieberman and the lifetime of public service he’s accomplished.

“Love or hate his politics, he’s just a good guy,” DePino said.

Olsen said he may not always agree with Lieberman’s positions, but he respects him. Lieberman’s announcement which comes on the heels of former U.S. Sen. Chris Dodd’s retirement from the Senate after 30 years means Connecticut will be losing all of its seniority in that chamber.

“Unfortunately, seniority is very important in the Senate. We’ll do the best we can to climb back up,” Olsen said.