Heilemann Talks to Wolfson About McCain’s Dismal Campaign and How KT Tunstall Might Have Won It for Hillary

Wolfson
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As the communications director for Hillary Clinton's presidential campaign, Howard Wolfson earned a reputation as aggressive, combative, gruff, and relentless — all qualities that will serve him well in his new job as a political commentator for Fox News, where he will often be paired with none other than Karl Christian Rove. But in reality Wolfson is a more complex figure than the caricature that formed during the brutal Democratic nomination battle between his boss and Barack Obama. An alt-everything music freak, a gourmand and collector of vintage watches, a history buff (his obsession with Bobby Kennedy is vast and intense), and a fashionista (alright, alright, we're kidding about this one, as anyone who remembers the sweater he wore on national TV on the night of the New Hampshire primary knows all too well), Wolfson is still recovering from Hillary's loss, which he took hard. That came through at times in an IM conversation on Thursday morning with New York's John Heilemann, but so did Wolfson's fierce loyalty to the Democratic cause — even though his party's ticket is being led by a man he did everything in his power to take down.

J.H.: So congratulations on your vacation and on your new Fox gig. How does it feel to be working at the heart of the vast right-wing conspiracy? And do you think it's going to be more fun butting heads with Karl Rove than with Mark Penn?

H.W.: LOL. (1) I watched an enormous amount of cable news during the last eighteen months and can say with great certainty that Fox was very fair to us during the primary. (2) They have cable's largest audience — an audience that progressives and Democrats need to talk to and make our case before. I have been fighting for Democratic causes and candidates for twenty years, and I certainly don’t intend to leave my politics at the door. (3) I think Karl may be slightly to Mark's left, so the arguments may be easier. (That was a joke.)

J.H. aside: No, it wasn’t!

J.H.: You and I have talked in the past about McCain's staggering weakness as a candidate. Can he win the general election if his performance remains so dismal?

H.W.: No. He is making the Bob Dole campaign of 1996 look well run. I think he has a case to make, but he sure isn’t making it.

J.H.: What would that case be?

H.W.: That he has spent his whole life in service to country, not party. That he has always been willing to take on Republicans when he thought they were wrong and reach across party lines to get real results and real reforms. Then he would have to provide some contemporaneous proof that he would do something different than George W. Bush has done. The country believes that Bush has failed — they are not interested in four more years of the same policies.

J.H.: The notion that McCain's case matters flies in the face of what some people (including me) believe about the fall campaign: that it's going to be a referendum on Barack Obama. Do voters believe that he's up to the job? Can they get comfortable with him and all he represents? Etc. Do you buy that argument, or do you really think it's a choice election?

H.W.: I think McCain has a case to make and he has not made it. I also think that Obama has to convince voters he can do the job, especially as it pertains to national security. Which I think he will do.

J.H.: How?

H.W.: I think this trip overseas will help. Speeches like he gave yesterday. They know what they are doing over there [in the Obama campaign].

J.H.: During the primaries there were a number things that HRC said that critics claimed would buttress McCain's case that Obama wasn't up to being commander-in-chief. (Specifically I’m thinking of the quote about how she and McCain have years of experience, while Obama has a speech.) Now that the Democratic war is over and Unity is felt throughout the ranks (ahem), do you wish that your former boss hadn’t said those things? Or do you think the critics were, and are, off base?

H.W.: There were points during the primary when Senator Clinton critiqued Senator Obama and vice versa. That’s how elections work.

J.H.: How would you advise Obama to deal with the situation if, say, McCain uses one of those HRC quotes against him in a debate this fall?

H.W.: He can say, "Senator, on the biggest foreign-policy decision since Vietnam you were wrong and I was right" — a line he used to good effect against HRC, if I recall correctly.

J.H.: You mentioned the foreign trip. As a message guru, can you lay out the risks and rewards that Obama faces while he's abroad?

H.W.: The rewards are high: Obama on a big stage, meeting with world leaders, looking presidential, greeted by cheering crowds waiting to fall in love with America again. The risk is if he trips up and says something that offends an ally — but I don’t think that’s likely to happen.

J.H.: Do you think he had no choice but to go to Iraq?

H.W.: He was getting hit on it — it was important to go, and he couldn’t go abroad and skip it. It’s an interesting bet that I think is a smart one. Imagine if John Kerry had gone to Europe and been greeted by adoring crowds — the GOP would have used it against him. Team Obama is betting that Americans want to see that the rest of the world is ready to like us again, and I think they are right.

J.H.: Would you have advised him to do his big Iraq speech before going or after?

H.W.: Probably after — but not a huge deal either way.

J.H.: This morning we got Obama's June fund-raising numbers, which were pretty impressive, if you ask me. Still, there were obvious tradeoffs in his decision to opt out of public financing. Given what we know now about the pace of fund-raising on both sides (by the campaigns and the parties), do you think Obama was wise, all things considered, to bail on the public system?

H.W.: Absolutely. Not even a close call.

J.H.: Even if it contributes to the burgeoning GOP argument that he's an expedient, unprincipled, flip-flopper?

H.W.: Yes. He’ll have a lot of money to counter that charge.

J.H.: So you think that, in the end, all sources of cash accounted for, Obama and the Democrats will have a significant and meaningful edge financially this fall? (This would have been a dum-dum question a month ago, but lots of people wonder now.)

H.W.: Yes. Now that the Clinton money is available to Obama, $50 million a month is the floor, not the ceiling.

J.H.: But the Clinton donors (at least at the high end) still seem pretty, er, unenthused about Obama. Do you think they will get onboard in a big way? And if so, what evidence would you cite?

H.W.: There is no way that Obama could have raised $50 million last month without at least some Clinton donors coming aboard. He won’t get all of them, but he will get a lot.

J.H.: The New York Times had a big front-page story on race and support for Obama yesterday. If you were working for his campaign, would the numbers in that piece about how white voters feel about him have freaked you out?

H.W.: They know they have work to do in that area, so I doubt it was a surprise to them. Having said that, every Democrat has work to do with white male voters.

J.H.: Certainly he has more work to do, given some of the stereotypes and misconceptions out there about him. Which brings me to this week’s New Yorker cover. What did you think? And do you believe that the Obama campaign's outrage was heartfelt or tactical?

H.W.: What seems satirical on the Upper West Side doesn’t always feel that way west of the Hudson. Both.

J.H.: Let’s talk about the V.P. question and then a final one on a topic close to your heart. On veep: (a) You said recently that HRC wasn't being vetted — is that still true to your knowledge? (b) Apart from her, who do you think would be Obama's best choice? (c) Same question for McCain.

H.W.: (a) I haven’t checked in the last couple of days; (b) Hillary; (c) Condi Rice.

J.H.: On (b), I said apart from Hillary!

H.W.: Can’t think that way.

J.H.: Fair enough. I think I know your arguments for Hillary — but why Condi?

H.W.: She is very popular, dynamic, and the choice would make history in its own way. And would help McCain compete for women and moderates.

J.H.: So you think he needs a game-changing pick?

H.W.: It couldn’t hurt.

J.H.: Okay, final questions. As a hard-core music aficionado of superb and eclectic taste, when you play the soundtrack for Hillary’s campaign in your mind, what songs do you hear?

H.W.: I stopped listening to music during the campaign. What I hear are the sounds of cell phones ringing and BlackBerrys vibrating — discordantly.

J.H.: So what are you listening to these days? New Age sounds of crashing surf and chirping crickets?

H.W.: BLK JKS, Glasvegas, Wild Beasts, Grizzly Bear, TV on the Radio, Beirut, Bon Iver, Julie Murphy and Fernhill, and Alina Simone.

J.H.: So how deep was the pain you felt when HRC’s supporters selected a Céline Dion track ("You and I") as her official campaign theme song?

H.W.: I was disappointed — I was pushing for KT Tunstall. I like to think we might have won had we gone with KT.

For a complete and regularly updated guide to presidential candidates Barack Obama and John McCain — from First Love to Most Embarrassing Gaffe — read the 2008 Electopedia.