The calculation was clear -- try to turn the potential negative into a positive, a strategy used by many a politician, including Al Gore during his 2000 presidential campaign.
But Gore's problematic trait was stiffness, not size. And by Wednesday, Christie had undercut his own strategy, saying a former White House doctor who expressed fears that his weight could be life-ending if he were president "should shut up" since she hasn't examined him and doesn't know his medical history.
The Letterman appearance was the clearest sign yet that Christie is well aware that his girth presents a potential obstacle in 2016, if not with voters than with the media. But by bringing it up as a joke, Christie effectively signaled it's acceptable to discuss it.
Despite his impressive skills as a politician, it remains to be seen whether he's ready to fully engage those who laugh about his appearance, which he insists he's working to alter through diet and exercise.
"I thought it was great to go on Letterman," said Paul Begala, a longtime friend and adviser of Bill Clinton, who was famously mocked by a cheeseburger-eating Phil Hartman on "Saturday Night Live" for his love of junk food. "Joking about one's shortcomings is always appealing and disarming. But then blowing up at [former White House doctor Connie Mariano] was a missed opportunity. She is a great doc and a great human being, and she was only saying what half the country was thinking."
Conservative commentator Bill Kristol, long an admirer of the New Jersey pol, was more pointed: "Christie's a very impressive pol. If he has a biology-related problem (and I'm not sure he does), it may turn out to be more his thin skin than his ample girth."
Christie, and Clinton, are not the only politicians to deal with weight struggles at a presidential level (Christie is seen as laying the groundwork for 2016 but has yet to say whether he'll run). Mike Huckabee, the former Arkansas governor and Iowa caucus winner in 2008, wrote a book about his weight struggles called "Stop Digging Your Grave with a Knife and Fork."
Yet Christie's weight struggles are far greater -- his size has prompted questions, and attacks, since his first successful election in 2009 against Democratic Gov. Jon Corzine. He stood out for telling Corzine to "man up and call me fat" after a TV ad with images that seemed to amplify his size.
And his Letterman appearance is not the first time he's used humor to defuse the issue -- he used a similar approach with Don Imus in 2009. But the use of the doughnut as a prop was different -- and refocused the discussion in a new way.
When asked by reporters at a press conference Tuesday, he soberly acknowledged his struggles with his weight and said he wants to shed pounds. He's well aware of the underlying concerns about his well-being, sources close to him say -- and his frustration with Mariano's remarks were rooted in his kids hearing that their dad faces serious health risks.
Regardless, it's less clear that joking about the weight, as opposed to losing it, will suffice in a modern-era presidential campaign -- a grueling marathon of plane rides, rubber-chicken dinners and sub-zero rallies.
"Gov. Christie is so talented and he has an Everyman appeal," Begala said. "But jokes alone won't get it done. My counsel would be to at least try to lose weight: work out, go on a diet. Mike Huckabee not only lost 100 pounds, he got a book deal out of it.
"President Clinton famously worked on his weight -- and seems to have won the Battle of the Bulge. Folks would be rooting for Gov. Christie and would empathize with his effort, even if he fell short. But you ought not attack a former White House doc and Navy admiral for expressing concern."
Sources in Christie's world point out that people are talking about his weight whether he jokes about it or not, so he attempted humor. They also push back on the health questions, noting he campaigned rigorously for months on Mitt Romney's behalf ahead of Hurricane Sandy. And after the storm, he was constantly in motion around the state, putting in 18-hour days, he later told ABC's Barbara Walters when she asked if he's too fat to be president.
"I'm the healthiest fat guy you'll ever meet," he told Letterman.
Huckabee, who has struggled with weight since losing it initially, downplayed Christie's problem as a potential campaign issue in a statement to POLITICO.
"I don't think it should be an issue unless it is for him," Huckabee said. "I was Governor when I was overweight and when I was thin -- I felt better, but I don't know that I was a better governor because of how much I weighed or didn't weigh. We have a President that smoked and openly admits to have used drugs. Why isn't that as big a deal as how many donuts Christie eats?"
Even if presidential politics are not Christie's immediate concern -- he is running for reelection with high post-Sandy approval ratings this year -- it's on the mind of his advisers.
To wit, Steve Grubbs, an Iowa-based political operative who worked for Herman Cain in 2011, said he just received a fundraising appeal for Christie's 2013 race. Still, Grubbs shared Huckabee's view that weight shouldn't be seen any differently than President Obama's nicotine habit.
"I think generally people see these personal vices as personal and I don't see it affecting the way people vote," he insisted. "If it exists out there, it's hard to measure and it's hard to get people to admit. The days of Taft are over ... People either love Christie for his frankness and how clear he is in what he believes or they're disconcerted by [his praise] for Obama ... I've literally never heard anybody say anything about his weight."
Chris Lehane, a former Gore adviser who helped devise the strategy to try to turn the vice president's renowned boring demeanor into a sign of his gravitas, said that making a positive of the negative is often the best option.
"At a certain level, smart politicians realize that it's often better to embrace a challenge ... if for whatever reasons he can't lose the weight, the next best option is to lean into it," Lehane said, recalling that at a certain point in the 2000 race, the decision was made to do just that with what was seen as Gore's deficient personality traits against the more charismatic George W. Bush.
Lehane called Christie one of the most talented politicians around and suggested he could end up making his girth an asset. The governor has dieted on and off over the past three years and has declined to join fellow Republicans who took shots at Michelle Obama's "Let's Move!" initiative.
Still, former Huckabee aides recalled vividly the extent to which the issue was discussed in 2008, at a point when the pol had already shed a lot of pounds and run a marathon.
"People constantly talked about it and they joked about it nonstop on the other side -- if there were cupcakes in the room or fried chicken," said Huckabee's 2008 campaign manager, Chip Saltsman.
One reporter, writing one of his first stories on the campaign, even asked to look in Huckabee's refrigerator, Saltsman said. The reporter opened the fridge and found a Reese's peanut butter cups package -- -- -- -- which Saltsman quickly claimed ownership of.
"Even if [Christie] lost 200 pounds tomorrow," he said, "it's going to be a constant conversation if he runs for president."
"Clearly he's trying to have a conversation with the American public about his weight issue, and I think the first person he needs to have that conversation with is himself," the GOP operative added. "He just needs to understand that if he kind of moves toward maybe running for president, that's the conversation people are going to have and the first person that needs to be comfortable with that conversation is him."
Ed Rollins, Huckabee's general consultant in that race, thought it was a mistake for Christie to continue drawing attention to it.
"He keeps raising the issue," Rollins said, noting that Huckabee did something similar by publicly celebrating his own weight loss after a doctor told him he had to because of diabetes, thus assuring follow-up stories when he started gaining weight again.
"There's no doctor [who's] basically going to say, 'You're in perfect health,'" Rollins said. "It doesn't work when you sit there eating a doughnut ... [it's] just a reminder of how fat you are."
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