President Barack Obama is introduced by campaign manager Jim Messina before he speaks at a campaign fundraising event at The Town Hall in New York, Wednesday, April 27, 2011. (Charles Dharapak/AP)

At 6:30 on Monday evening, Obama 2012 campaign manager Jim Messina walked up Fifth Avenue on the Upper East Side of Manhattan, dressed as the spitting image of the Wall Street bankers he hoped to impress.

“Do you like this?” he said smoothing down his red striped tie. The rail-thin operative wore a dark suit and was accompanied by an aide swinging a tautly wrapped umbrella. “I think it looks pretty good!”

Messina then turned toward the red brick townhouse of millionaire Wall Street hedge fund director Marc Lasry, where, for the third time that day, he made a fundraising pitch to investors whom his boss once vilified as “fat cats.”

Messina’s visit to Lasry’s home is a clear sign that the fundraising season for President Obama’s reelection campaign has begun in earnest and that his team is operating in a markedly less sensitive political climate than last year. These days, the object is to raise $700 million, and Messina is not as discerning as he once was about where it comes from.

Last summer, the White House political team, which Messina ran, sensed a political odor emanating from the crystal chandeliers and European masterpieces of Lasry’s home and pulled the plug on a high-dollar fundraiser for Obama there. But with campaign 2012 on the horizon, Messina and company are apparently more willing to hold their noses and pass the hat on Wall Street, especially to Hillary Rodham Clinton’s 2008 donors in the crowd.

Monday’s meeting at Lasry’s home was expressly organized as an opportunity for Messina to reach out to erstwhile Clinton supporters, a group the administration hasn’t exactly showered with attention.

“Everyone’s pumped up,” said Messina as he backed toward the house and ducked into the foyer. “We’re going to get this guy elected!”

A different landscape

Democratic officials speaking on background and potential donors and fundraisers who met with Messina at Monday’s numerous meetings had a more clear-eyed view of the campaign manager’s immediate goals and how they contrast with his former aversion to the Lasry manse.

“The difference between then and now is they need you more,” said one attendee of the Lasry event, which was billed as an outreach to former Clinton supporters. The donor, who spoke on the condition of anonymity to discuss the thinking of top fundraisers, said that Messina’s meetings in New York mark the beginning of a courting process that will culminate in a major date with Obama at the upscale Manhattan restaurant Daniel in June. Fundraisers expect that event to rake in millions.

A senior Democratic Party official with intimate knowledge of the campaign’s fundraising efforts confirmed that there was “an appropriate need to be careful” last year about seeming too close to Wall Street as the president pushed financial reform on the Hill. Now that the majority in the House has been lost to Republicans, the official said, “this is no longer the season to move legislation.”

According to several recipients, Lasry sent e-mails to former Clinton fundraisers, including prominent Clinton donor and confidant Alan Patricof, inviting them to the Monday event at his home. (Patricof did not attend because he was traveling on the West Coast.)

There was no admission fee for potential check-gatherers, known as “bundlers,” which made sense, because many of the Wall Street power brokers in attendance weren’t thrilled about financial reform and had preferred Clinton as a candidate to Obama. After the 2008 Democratic primary, however, many Clinton stalwarts donated to Obama in the general election.

But Messina’s goal, the attendee said, was to make them “huge supporters of Obama. The question is: Are you going to give, or are you going to go out and raise a half a million or a million bucks?”

There is no better place to forge an alliance than at Lasry’s townhouse. It is considered neutral ground by the Obama campaign, which counts Lasry as a committed supporter, and former Clinton backers. Lasry, a founder of the hedge fund Avenue Capital Group, which once employed Chelsea Clinton, has unassailable Clinton credentials and connections.

“Lasry has a network that the president didn’t get to tap into that aggressively last time because of the protracted primary,” said the senior Democratic official. “He’s seen as an honest broker by others in that world, and he is seen as something of a thought leader in this work. And he has a reach beyond New York.”

The Obama campaign was at pains to play down any suggestion that it was targeting Clinton donors or returning hat in hand to the Wall Street moguls it attempted, with mixed success, to chasten.

“There are many individuals in the financial sector who support the President and his efforts to get the economy back on track,” Katie Hogan, a spokeswoman for the Obama campaign, said in a statement. “And to put in place the protections necessary to ensure that the financial crisis will never reoccur.”

Sense of urgency

Before the Lasry event, Messina had several meetings with more enthusiastic audiences. In the afternoon, Jane Hartley, chief executive of the consulting firm Observatory Group, who has emerged as a top Obama fundraiser in New York, held an event for Messina at the University Club attended by the original cadre of the state’s Obama supporters. That group included Orin Kramer, an investor at Boston Provident; James Torrey, an investor at Torrey Funds; and relatively new arrivals such as Roger Altman, chairman of Evercore Partners, and Vincent Mai, chairman of the board of Sesame Workshop. They listened to Messina talk about the campaign’s plan to stress infrastructure and job-creation programs.

Messina also discussed campaign strategy. According to one attendee, he said that the target number for the campaign was not $1 billion, as has been reported, but closer to $700 million. The campaign expects to hire 4,000 to 5,000 paid staff members compared with 3,000 last time, Messina said, according to the attendee.

He also sought to pump up the group, saying the campaign would not let the Republican field’s attacks on Obama during the primaries in Iowa, New Hampshire and South Carolina go unanswered. Instead, according to the attendee, Messina quoted his “favorite philosopher, Mike Tyson,” saying, “Everybody’s got a plan until I punch him in the face.”

At an earlier event with investors in Midtown Manhattan, Messina explained to executives from the city’s financial, industrial and media sectors why they should raise cash for the president, according to one attendee. Significantly, the gathering was held by Josh Steiner, a co-founding partner of the hedge fund Quadrangle Group with Steven Rattner, the Obama administration’s former car czar. Rattner, who has since left Quadrangle and become ensnared in a pension fund scandal, was once half, with his wife, Maureen White, of the first couple of New York fundraising. Their palatial apartment was a frequent Clinton haunt.

On Tuesday, Messina met with more investors at the office of Clinton fundraiser Blair Effron, co-founder of Centerview Partners, and Lasry’s brother-in-law.

The constant at all the New York events was Messina’s effort to imbue potential bankrollers with a sense of urgency. That is no easy task. The Republican presidential contenders, ultimately, could be the Obama campaign’s greatest fundraising challenge.

“The problem is that when you look at the Republican field, there isn’t that anxiety level,” said the attendee at the Lasry event, who explained that the lack of a looming threat translated into a lack of immediacy that made it more difficult to collect checks for the president.

“It’s not that scary.”