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Interesting read — Jeb Bush, prep school rebel

David Margolick from Vanity Fair recently revisited some earlier work he’d done on Jeb Bush’s days as a difficult-to-pigeonhole tennis team captain and small time rum-runner back at Phillips Academy Andover, the prestigious Massachusetts boarding school that the patrician — yet Texan — future Florida governor called home from 1967 to 1971:

“There was a kind of arrogance to him,” one of them told me, describing Bush’s membership in a “clique of wealthy kids.” “I remember him smoking a lot of dope,” he added.

But bring up Jeb Bush to him and other classmates now and they’re considerably more reticent, either because the stakes, or the level of Bush fatigue, have grown so much greater in the meantime. “You’re certainly a pal,” this fellow, whom I knew independently, e-mailed the other day. “However, I think I’d like to skip Jeb this time.” I pressed him. “Last week I found myself getting a headache talking with someone in the same context for 20 seconds,” he replied. Then he went silent.

I hadn’t thought much about my 2001 piece, “Brother Dearest,” until I recently encountered a 2013 posting about Jeb on Capitolhilloutsider.com by former Republican Congressman John LeBoutillier, in which LeBoutillier claimed Bush had ratted out one of his partners in a campus rum-running operation to save himself. LeBoutillier says he picked up the story at a Harvard reunion from one of Bush’s Andover contemporaries, and later confirmed it with another. (Also involved in the operation, he incorrectly told me, was Bill Belichick, the current head coach of the New England Patriots, who was then spending a post-graduate year at Andover.)

LeBoutillier got a few, key details wrong, according to one of the organizers of the endeavor: The Andover “distributorship” was only for booze, and Bush’s role in it was peripheral. Belichick had absolutely nothing to do with it. And since the perpetrators never got caught, there was no one to rat out. But LeBoutillier appears to be getting his wish: the Boston Globe is now on Jeb’s case. In the meantime, accepting LeBoutillier’s dare, I’ve tried to refresh my story from 13 years ago. It’s not been easy.

For a politician who never got the same effete reputation as his equally blue-blooded father, one gets the idea that Jeb’s time at Andover was both familiar and uneasy. Margolick sees a comparison to fellow GOP pol with plutocratic roots:

Though they had more pressing matters to discuss—like how they can run for president simultaneously without knocking one another out—perhaps Bush and Romney swapped prep school stories during their powwow in Utah this week. But while Romney famously forgot the hair-cutting episode, Bush seems to have some insight into his former preppie self. “I was,” as he once put it, “a cynical little turd at a cynical little school.”

Written By

Ryan Ray covers politics and public policy in North Florida and across the state. He has also worked as a legislative researcher and political campaign staffer. He can be reached at ryan@floridapolitics.com.

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