Roger Stone is one of the last guys on Earth one would expect to feel guilty over an episode of rough and tumble politicking. As a self-admitted hit man for the GOP, Stone has had a hand in everything from Nixon's dirty tricks to Eliot Spitzer's resignation to spreading discredited rumors of a Michelle Obama “ whitey” tape during the 2008 Democratic primaries. You might call Stone the Forrest Gump of scandal, popping up to play a bit part in the most notorious negative campaigns in recent history.
The capstone of Stone’s career, at least in terms of results, was the “Brooks Brothers riot” of the 2000 election recount. This was when a Stone-led squad of pro-Bush protestors stormed the Miami-Dade County election board, stopping the recount and advancing then-Governor George W. Bush one step closer to the White House. Though he is quick to rebut GOP operatives who seek to minimize his role in the recount, Stone lately has been having second thoughts about what happened in Florida.
When I look at those double-page New York Times spreads of all the individual pictures of people who have been killed [in Iraq], I got to think, 'Maybe there wouldn't have been a war if I hadn't gone to Miami-Dade.’
"There have been many times I've regretted it,” Stone told me over pizza at Grand Central Station. “When I look at those double-page New York Times spreads of all the individual pictures of people who have been killed [in Iraq], I got to think, 'Maybe there wouldn't have been a war if I hadn't gone to Miami-Dade. Maybe there hadn't have been, in my view, an unjustified war if Bush hadn't become president.' It's very disturbing to me."
Stone voted for Bush in 2004 as well (“John Kerry was an elitist buffoon”) but he pulled no punches in his assessment of the last eight years. Stone's own political philosophy is libertarian, and he says it conflicts with Bush's penchant for expanded executive power.
“I think across the board he's led the party to its current position, which means losing both houses of congress and now the White House,” Stone said. “How can you be conservative and justify wiretapping people without a warrant? We're supposed to be the party of personal freedom and civil liberties. Big brother listening in on your phone calls—I got a problem with that.”
That Stone joins Matthew Dowd, Scott McClellan, and Colin Powell in the group of disaffected ex-Bushies shouldn’t come as a complete surprise. Stone advised Donald Trump on his prospective bid for the presidency in 2000. According to Stone, he didn't even want to get involved in the 2000 race at all until the GOP's recount head, James Baker III, called him up and asked him for his help. Stone said that Baker had helped him out in 1981 by getting Reagan and Bush to lend support to New Jersey Governor Tom Kean, whose campaign Stone ran. He owed him a favor.
“In this business, if you don't pay your debts you're finished,” Stone said.
Nor does Stone regret dirty politicking. Stone still offers his services as a no-holds-barred strategist to domestic and foreign politicians alike, and claims his client list is full. Ironically one Florida race this year even hinged on his role in the 2000 recount. In a hard-fought campaign for Broward County sheriff, the Democratic candidate, Scott Israel, flooded the airwaves with over-the-top ads attacking his Republican incumbent Al Lamberti for utilizing "the same Bush hatchet man who tried to steal the 2000 election." Obama carried Broward County by 243,567 votes, the biggest margin of any county in Florida, but incredibly, Israel lost to Lamberti by 15,400 votes, a rare Republican upset in an overwhelmingly Democratic year. Stone may be paying a price for the 2000 recount in his conscience, but he didn't pay one at the ballot box.
Benjamin Sarlin covered New York City politics for The New York Sun and has worked for talkingpointsmemo.com.