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If you wanted to conjure up an unlikely photo op—something along the lines of George W. Bush in a loving arms-around with Dennis Kucinich—you might try putting skinny Barack Obama in a happy embrace with burly Teamsters union leader Jim Hoffa Jr.

These are not exactly birds of a feather. But there they were last week, grinning and gripping in San Antonio, as Hoffa vowed to put DRIVE—the union's powerful political-action committee—in gear for Obama in the upcoming campaigns.

It's an odd-bedfellows alliance that represents a major shift for the union, as well as one more indication that Obama-mania can jump all divides.

Just a few months ago, the surest way to find a passionate Obama supporter was to head for the nearest WiFi-enabled coffeehouse. If there was a Teamster around at all, he was probably out back delivering a truckload of latte cups. Hoffa's 1.4 million members wear the bluest of America's collars. They're freight drivers, warehouse workers, trash haulers, even cops. If they went looking for a Democrat in the early primaries, they were more likely to go for John Edwards, who at least tried to speak their language.

And when it comes to Teamsters, the Democrat part is hardly a given. This is the union that backed Richard Nixon and Ronald Reagan. A short-lived liberal era under ousted reformer Ron Carey ended abruptly with Hoffa's election in 1998. The new union chief made a big point of saying that the Teamsters would no longer be an "ATM for the Democratic Party."

Hoffa gave a late and half-hearted endorsement to Al Gore in 2000. But by Labor Day 2001, Bush and Hoffa were chummy enough for the president to chow down some ribs at a big Teamsters Labor Day barbecue in Michigan. There, Bush praised the union leader, who was helping lobby Congress for a pet GOP project to allow oil drilling in Alaska's Arctic National Wildlife Refuge.

But that was then. Bush's refusal to heed the union's complaints about allowing low-paid Mexican truckers to haul NAFTA-spawned goods across the border soured relations badly.

Hoffa went looking for a winner in 2004 with his friend, ex-Missouri congressman Dick Gephardt (whose old man was a Teamster milkman), then signed on with John Kerry after Gephardt faltered. But again, there was no full-court press by the union.

This time, with an endorsement right on the eve of crucial primaries in blue-collar-heavy states, the Teamsters finally seem to have settled on someone they actually like. And wouldn't you know it, the union that's long served as a national stereotype for beer-drinking Archie Bunker types has picked a jug-eared black lawyer from Harvard who looks like he couldn't find the air brake in an 18-wheeler.

And if that kind of irony gets you giddy, consider that Obama's most constant comparison these days is to the Kennedy brothers: That would be Robert F., who once tried to take a swing at Hoffa's dad outside a Senate hearing room and later helped send him to prison, and John F., whose assassination, according to claims by Hoffa Sr.'s own late lawyer, was co-engineered by the late Teamsters big.

Not that anyone believes that stuff.

Whatever the unlikelihood of this labor-latte alliance, Obama's 10 straight wins and his rock-star rallies have made Hoffa a believer. "He is the candidate in the best position to lead our movement to restore the American dream to working people in this country," said Hoffa last week.

An unspoken factor in the endorsement may also have been some lingering suspicion among Hoffa and his aides from the days when the Clintons were closely aligned with Carey, Hoffa's hated predecessor, who was forced out in a campaign-funding scandal. There was also pressure to make a clean sweep of the big unions that, along with the Teamsters, broke away from the AFL-CIO three years ago to form the rival group Change to Win. SEIU, the service employees' union, has already gone for Obama, as has UNITE-HERE, the clothing and hotel workers' union, along with the United Food and Commercial Workers.

But Hoffa insisted that the endorsement followed the results of internal union polling that showed Obama was well-liked by his members. The union declined to give specifics, but several people familiar with them said the surveys found that local officers went heavily for Obama and the membership gave him more than 60 percent approval ratings. Both McCain and Clinton registered substantially lower.

Still, the decision wasn't easy. "I gotta tell you, there was a fierce debate on the executive board," said Dan Kane Jr., who heads a Bronx trucking local. "It wasn't anti-Hillary—she's our senator, and we've supported her before and will again. It was just who we thought could win." Kane, a second-generation Teamster whose father is a close Hoffa aide, said he wrestled with his own vote in last month's primary, ultimately opting for Obama. "I am thinking the only times the Democrats have won has been when someone energetic ran. I think we need some excitement now. If the young people show up for this one, I think we have a good chance."

Gregory Floyd is the new leader of Local 237 in Manhattan. His is the largest Teamster local in the country, with 24,000 members, many of them city employees, and another 8,000 active retirees. As with most New York labor unions, Hillary Clinton looms large in his world, but he said that his local was still going with Obama. "We know that we need to defeat the Republicans and turn the country around," said Floyd last week. "The endorsement of Barack Obama is a good one. We are going to be a political powerhouse in this fight."

The endorsement has also bridged the Teamsters' long-standing divide between those who once backed Carey and the Hoffa forces. Sandy Pope, leader of a Queens-based local that represents warehouse workers, ran two years ago on an anti-Hoffa slate. But last week, she praised his endorsement in the presidential primary. "I think it's great," she said. Pope noted that Obama had proved himself with wins in states like Wisconsin, Missouri, and Minnesota where the Teamsters have many members. "My argument to Teamsters is that when you see the states Obama took in the Midwest, it makes a stronger argument for winning our members in places like Ohio and Pennsylvania."

The union is no small presence in those battleground states. It has some 60,000 members in Ohio, which votes on March 4. Assuming that the race is still on by April 22, when Pennsylvania votes, the union has 80,000 members there, along with a long tradition of playing a big role in local and statewide races.

Despite the union's endorsement, Clinton still retains the loyalty of New York's most powerful Teamster, Gary LaBarbera, who heads both the council overseeing local Teamsters affairs as well as the million-member New York City Labor Council. "He's sticking with Hillary Clinton, who he thinks is a great leader," said Carolyn Daly, a council spokeswoman.

Members of LaBarbera's Local 282 haul construction material and debris, and last month, the union's name surfaced in the big Gambino crime-family case in Brooklyn. Some of the schemes charged in the indictment stem from trucking employers who allegedly used mob muscle to scam the union out of benefits owed on behalf of employees.

But unlike the bad old days when John Gotti's gang ruled the roost at the local, LaBarbera helped squelch the scammers. He did so by retaining an independent, court-supervised investigator who helped break the case. The investigator, Robert Machado, was first to spot the schemes, tipping off federal investigators at the Office of Labor Racketeering. "I got nothing but cooperation from LaBarbera," said Machado.

Like this year's presidential race, it's another one of those things that would baffle Bobby Kennedy and Jimmy Hoffa Sr. if they were around to watch.