Why Curt Schilling Could Win Teddy's Seat

There were a lot of smirks adorning the faces of Bostonians yesterday morning, presumably a collective judgment on the revelation that retired Red Sox pitching ace Curt Schilling is contemplating a run for the late Teddy Kennedy’s Senate seat. Of course, those are probably many of the same folks who gave up the ghost back in 2004 when Schilling, bleeding team colors from an ankle tendon that had been stitched up in Rube Goldberg fashion, limped out to the mound against the New York Yankees in a desperate moment on Boston’s path to its first championship in 86 years. So could Schilling’s path to Washington and Congress be any more improbable than that?

It has long been assumed that Schilling, 42, with his outspoken activism including high-profile campaigns to raise money to fight ALS and to boost awareness of the dangers of skin cancer, harbored political ambitions. But most believed he would run for the Senate from Arizona, where he also pitched a team to a World Series title and where his strident conservatism and born-again faith would be more in fashion with voters than in the blue-state bastion of Massachusetts. But Arizona appears blocked, with Jon Kyl ensconced as Senate minority whip and John McCain showing no sign of wanting to retire to any of his homes. Massachusetts has the obvious virtue of an open seat with no obvious successor to Kennedy. So far Schilling has only allowed─on his popular blog, 38pitches.com─that he is considering the possibility of a Senate run, but that “many, many things would have to align themselves for that to truly happen.”

That cryptic sentiment is rather strange for the shoot-from-the-lip Schilling, who is famous for firing verbal brickbats at reporters, drug cheats, and anybody else who riles him. Still, most political pundits would recognize it as a euphemism for requiring serious money to finance a significant campaign. It’s hard to imagine that would prove a problem. Schilling curried favor with the national GOP by campaigning for McCain in last year’s presidential election and, even more notably, for George W. Bush against Bay State Sen. John Kerry following the 2004 World Series triumph. Moreover, it would be hard to imagine a bigger blow to the Obama administration agenda than seeing the man eulogized as the heart and soul of the Democratic Party replaced in Washington by a conservative Republican.

Beyond any bankroll, Schilling possesses significant assets in what will be little more than a four-month campaign. Unless one of the Kennedys─most likely Teddy’s nephew, former congressman Joe Kennedy─wants to claim the family mantle, Schilling would be the biggest name in the race, and he has already established a legacy in the heart of Red Sox Nation that no other candidate can rival. Just by entering the race, he would challenge Sarah Palin’s status as the nation’s most prominent Alaska Republican. (Schilling is from Anchorage.) And he is both brighter (though he never graduated from college) and far more articulate than Palin, as well as exceptionally savvy about both traditional media and new technologies that enable him to reach his audience directly.

Nor is Schilling quite as mismatched with Massachusetts as its liberal reputation might suggest. The state has long boasted a prominent stripe of conservatism─Reagan carried the state in both 1980 and 1984─and before the current governor, Democrat Deval Patrick, four different Republicans, including Mitt Romney, held the office for 16 years. Until the national stage propelled him rightward, Romney demonstrated that a conservative stance on economic issues coupled with a moderate, hands-off approach to social issues was a powerful political formula in Massachusetts─and one that Schilling likely would mimic. With Patrick’s poor approval ratings and simmering voter resentments against the Democratic stranglehold on state offices, a backlash could bolster Schilling’s surprise candidacy.

Yesterday Schilling told Boston’s WEEI radio that apart from “the whole media-spotlight crap,” a Senate “fight” would be “a lot of fun.” Not half as much fun as it would be for the rest of us.