The Bill Weld who governed Massachusetts from 1991 to 1997 fits the profile of the type of Republican you might expect would jump ship and endorse Barack Obama — something that Weld is set to do this morning.
In his 1990 campaign, he actually ran to the left of his Democratic opponent, the combative former president of Boston University, John Silber, scoring points with Massachusetts’ socially liberal suburbanites by stressing his pro-choice, pro-gay-rights, and pro-environment views. (Only on taxes did Weld strike a more conservative posture than his opponent.)
And once elected, he earned stratospheric popularity by defining himself in opposition to the cultural conservatism of the national Republican Party. Weld used his speech to the 1992 Republican convention in Houston to attack the party’s anti-abortion plank, a tack that earned him loud boos in the hall — and better poll numbers in Massachusetts. He also proudly appeared on the cover of a gay magazine in 1993 under the headline, "The most pro-gay governor in the country," and as national Republicans lustily pursued investigations of the Clintons, Weld thumbed his nose at them and offered to appear as a character witness for Hillary Clinton. When Bill Clinton nominated him as ambassador to Mexico in 1997, Jesse Helms single-handedly blocked the nomination. (Not that Weld minded too much; he’d merely been looking to escape the governorship, which he resigned when he was nominated, and liked the publicity he received from fighting Helms.)
It’s entirely consistent with this Bill Weld’s history to endorse Obama over John McCain. Weld’s move is only a surprise in the context of his jarring moves to the right earlier this decade, when he got it in his head that he could be elected governor of New York, where he moved after leaving his family in Cambridge in 2000. In Massachusetts, home to a virtually nonexistent Republican Party, he was able to run as a moderate and claim the ’90 gubernatorial nomination with independent (and liberal Republican) votes. In New York, though, he needed conservative Republicans and the Conservative Party itself.
So, very awkwardly, the man who once matter-of-factly talked about all of the gay weddings that he’d attended tried to back-pedal and curry favor with the pro-life and anti-gay-rights wing of the party. This was, of course, a miserable failure; conservatives weren’t about to forget how Weld had built his Massachusetts career by defining himself against them.
Now, at 63, Weld is almost certainly finished in elected politics. Residual loyalty to Mitt Romney (back when Romney was a pro-choice moderate, Weld helped recruit him to run for the Senate in Massachusetts in 1994, and Romney returned the favor by raising money for Weld’s 1996 Senate campaign) compelled Weld to support his presidential campaign earlier this year, but he has no such ties to McCain, nor does he have any need to pretend to pretend to be a social conservative anymore. So the old Bill Weld is back, and he’s endorsing exactly who you would expect the old Bill Weld to endorse.