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Flynn is everything Kerry is not. He is an Irishman who still lives in the same South Boston house he bought in 1968. His mother cleaned offices, and his father was a union dockworker. When he was mayor in the 1980s, about 10 of his relatives were on the city payroll. In 1993, Flynn got injured trying to defuse a racially charged fight at South Boston High. Flynn was known for his way of talking quietly to people and listening just as intently. In the midst of Flynn's third term, President Clinton made him the U.S. ambassador to the Vatican.
When Kerry returned to politics in 1982 to run for Lieutenant Governor, the two men hardly knew each other. In the days leading up to the race, Kerry was worried that he would lose, according to John F. Kerry, the 2004 biography written by Boston Globe reporters. At a Labor Day festival in Boston shortly before the primary, the two men had their first conversation, Flynn says. At the time, Flynn was an enormously popular city councilman. And he knew only that Kerry had gone to Vietnam. "I just felt that, hey, this was a rich kid who could've avoided military service, and he didn't. It was no more complicated than that," Flynn says. "I said, 'I admire your service to your country. I don't know if you're going to win or not--probably not. But if you want me to support you, I'd be happy to do it.'" That day, Kerry's campaign held a press conference to announce Flynn's backing. Flynn sent his supporters into the streets on Kerry's behalf. "That was the end of it. He won, obviously," says Flynn, taking a sip of his cocktail.
Two years later, when Kerry catapulted into a Senate race, he got Flynn's support again--and it was even more crucial. Flynn campaigned for Kerry against the wishes of labor unions and his old friend Tip O'Neill. Flynn says he supported Kerry out of loyalty. The relationship was straightforward and pragmatic, as Kerry's tend to be. "We've never been out to dinner, never sent each other a card," says Flynn, sounding a little mystified.
By this time, Flynn was Boston's mayor, which meant he could send some 7,000 of his supporters into the streets to campaign for Kerry. Two weeks before the primary, Flynn introduced Kerry to union leaders at their annual breakfast at the Boston Park Plaza Hotel. He also escorted Kerry to the city's Irish pubs at happy hour. "It was a bit awkward for him. It's not exactly the place where he would hang out," Flynn says. "But people just needed a little reassurance." Kerry won the primary, just barely. In 1984 he was elected to the U.S. Senate.
After all these years, though, Kerry may have lost the backing of Ray Flynn. Citing his opposition to Kerry's support of abortion rights, Flynn says he is not sure whom he will vote for this year. And the more he talks, the more it sounds as if he still does not know who Kerry is. "John never went out of his way to talk to people that don't agree with him or do anything that didn't fit into his grand plan," he says at one point. Yet later on, he relates how Kerry quietly brought pizza and sports books to his son Ray Jr. when the young man was hospitalized with severe depression.