The Strategist: How to Win Elections with Jim Messina

In an exclusive Mace interview, William Cash talks to Jim Messina, the man known as The Fixer for his success in both Obama and Cameron election campaigns.

Photo by Charles Dharapak/AP/Shutterstock (5955960a)
Photo by Charles Dharapak/AP/Shutterstock (5955960a)

There was a time when Jim Messina was described in the media as “the most important man in Washington you’ve never heard of”. But such anonymity is no more.

Today, thanks to turning around the flagging Obama campaign of 2012 and pulling off a similar miracle for Cameron in 2015, Messina is right up there in the Olympian clouds of the DC Beltway election campaign manager hall of fame. And he’s only just turned 50.

Messina began his career as a college senior in 1993 when he managed the successful reelection bid of the mayor of Missoula in Montana. Today he has a track record that has elected 12 presidents and prime ministers around the world.

Has politics become more glamorous since the days of his early dawn-to-dusk battle busrides? “Absolutely,” he jokes. “People are now making movies and TV shows about idiots like me.”

Only the self-effacing Messina – a political junkie since he was 10 – is no such thing. He’s the first US campaign manager to turn his data-driven “playbook” – focused on aggressive digital messaging and a relentlessly professional “ground game” – into a successful global corporate strategy business. On leaving the White House, he founded The Messina Group (TMG), which now has over 300 international clients and offices in DC, London, LA, San Francisco and Denver.

As Messina’s face comes into view on myZoom screen – despite being a Democrat, he reminds me of a young William Buckley Jr debating Gore Vidal – I can see he is bunkered up in in what looks like a large, rustic cabin-like house, a sort of Camp David of TMG. Due to the fires, a strange, chalky white smoke is visible in the cabin’s windows.

Messina’s location may make him seem isolated, but he does in fact rank alongside other iconic US strategists such as James Carville (aka the Ragin’ Cajun of The War Room fame and the man behind Clinton’s 1992 White House win), David Axelrod (chief strategist of the 2008 Obama campaign), Ed Rollins (manager of Reagan’s 1984 campaign) and his protégé Lee Atwater who died of brain cancer aged just 40 but was the Machievellian architect of George HW Bush’s 1988 victory, famed for his “dirty tricks” campaign of racial messaging against Michael Dukakis.

But when I mention this roll-call of maverick legends, I point out that none of the above went on to found a global corporate strategy business, with clients ranging from Uber to Google. What makes him different?

“You know, Carville’s now one of my best friends, but he just has no interest in the business side. And I studied Lee Atwater but he had no interest [outside of politics]. And a lot of these guys just think I’m fucking crazy because I can do whatever I want in politics and I’m out there talking to tech guys that they think are assholes. But you know, it’s just a different thing for me. I’m just incredibly fascinated by innovation.”

He is known as The Fixer, winning what he calls the 2012 “dream race”, largely thanks to embracing technology as well as heavily investing in an innovative social media digital strategy that won votes online as well on TV. He has never wanted to do anything else since the age of ten (other than be quarterback for the Denver Broncos). With a smile, he says there are “only 13 drinking days left until the first TV debate”, an event he can hardly wait to watch (Messina has a waspish sense of humour and a colourful vocabulary).

With the slogan “Good fights are in our DNA”, TMG advises global business leaders, FTSE 100 CEOs and is feted at Davos. Messina is one of the world’s most in-demand campaign strategists. After starting in 2013, with just two former staffers, and operating out of what he calls a “borrowed, windowless office” the group now has a track record of having elected more presidents or prime ministers than any other strategy outfit in history.


London callingOne of his very first calls after deciding to launch his new consultancy back in 2013 was to David Cameron. He had first met Cameron in 2009 during Obama’s first state visit to Britain during a bilateral meeting.

Despite Cameron being an Eton educated Conservative and Messina a die-hard Democrat (“from the wrong side of the tracks,” as he says), they just clicked. “David had yet to win in 2009. He was in an opposition meeting with Obama so we met and talked for a while. And I was super impressed with Cameron. Really smart. And I was like, oh, that’s interesting.”

Then Cameron’s team called Reggie Love, Obama’s assistant at the White House, and said they wanted to meet with Messina. So in early 2013, Cameron’s team flew over to DC, among them Lynton Crosby, the Australian strategist who had masterminded Boris Johnson’s winning mayoral campaign, and Andrew Feldman, Cameron’s old Etonian tennis partner and former chairman of the Conservative party. The Cameron-Messina courtship began to get serious.

“And then my wife and I flew over and Cameron cooked dinner at Number 10 which was funny as I didn’t realise Downing Street isn’t like the White House. David actually had to cook dinner. He was making me pasta. And he said, ‘Jim, I got you beer’, and he handed me a Budweiser which I thought was funny because nobody in America drinks it! And then we spent a long time talking and I really appreciated his vision of what he was doing for the Tories in terms of modernising them – and the stand he took on same-sex marriage, all those things”.

Didn’t you think it strange, as an American Democrat, to be flirting over pasta with a posh public-school Conservative?

“I think I heavily underestimated the reaction in America: an Obama guy working for the Conservative Party. But that’s another story. Because, you know, in some ways Tories are just moderate Democrats, right? American politics is so much more conservative that, you know, I just didn’t have any problem with the things he stood for. They all were very Obama-like things. He used to tease me that he was more liberal than Obama was on climate change and other things.”

What became clear was that Cameron’s inner circle – including George Osborne – wanted to hire him to apply the US campaigning methods of the extensively tried-and-tested Messina playbook. This goes back to fourth grade when he wrote a paper saying that when he grew up he wanted to be the president’s campaign manager. “I always was going to be in politics,” he says. “I went to school and got dual degrees in politics and journalism.”

The Trump card

The day he left the University of Montana, Messina was named political director of the state Democratic Party. He soon was being described as “the Orca whale you don’t see”. In The Bonfire of the Vanities era when 95 per cent of college graduates wanted to work in Wall Street or the City, nobody wanted to work for peanuts on some congressman’s campaign team. But today, he says, that has all changed. Working in lobbying in Westminster or the Beltway is where the smart kids can be found applying for jobs.

“For the first time I have people coming up to me and saying they want to be a lobbyist. And I’m like, no one wants to be a fucking lobbyist. Lobbyists don’t want to be lobbyists. And yet, you know, that’s what the cream of graduates are doing.”

Messina is known as a master of turning around what campaign staffers call the “shit sandwich”. Which is one reason he is cautiously optimistic that Trump won’t land a series of bare-knuckle knockout punches against Biden in the first TV debatee.

Incumbent presidents often fail in their first TV debate. An exception was in 1976 when Ford got the better of Carter but he then lost the second on foreign affairs.

“Obama did terrible in his first debate, Bush did super bad at his, Clinton was horrible in his – it’s just true in all these debates,” says Messina. “Trump’s other problem is he hates rules, right? And so I watched him the other night in a town hall. Trump was pathetic because, you know, George Stephanopoulos just wailed away on him. And he just looked there stunned because no one ever gets to question him. And that’s going be what the first debate is. Just two-minute answers. So I’m super interested”.

The debates, Messina adds, are going to be much more important than traditional American debates because normally the US campaigns kick off with the conventions. But this year, because of Covid, “no one watched the conventions”, especially swing voters in the battleground states. When I mention that Peter Mandelson – campaign manager of Tony Blair’s 1997 UK election victory – has written in his Mace diary that Biden “needs to take the gloves off”, Messina reminds me that in 2012, it was Biden’s bullish performance in the vice president debates that helped drag the Obama campaign back on track. He can be good at “one-liners”. To do well against Trump he needs to punch back in an “authentic way and that’s harder”.

“Trump has spent six months saying Biden can barely get a sentence and his ads are saying he’s a doddery fool. Biden has to do two things to come out well. His campaign message is all about how he’s going to return this country to stable government. So he has to come across as the normal guy who gets tough and he can’t be a crazy lunatic.”

America is different from the UK, he adds, in that there’s “way less emphasis on swaying swing voters. In the UK, there are between 20 and 35 per cent undecided voters, and you can vote for two or three major parties. But in the US electorate, there’s only eight to 10 per cent of swing voters who might vote for either and that’s it. And those people think about politics for four minutes a week.”

It was this insight that helped Obama win in 2012, and it was these insights along with spending 2014 building the Conservative Party’s hopelessly inadequate data modelling systems that led to Messina shaking up the 2015 Conservative election machine

‘‘You don’t hire an American political consultant like me because I’m so much smarter than everyone else. Because Lynton Crosby is just as smart as I am. You hire an American political consultancy because we have a billion-dollar system and we’ve tried everything and we have gone through everything. So a lot of the things we had done in the Obama win, the Tories had just never done before because they didn’t have the money, or it just wasn’t the way you did it in UK politics. It was also a partnership because you had a campaign manager in Lynton who wanted to do some new stuff and didn’t feel territorial’.’

Nuts in May

His “one big regret” in politics is working on the Theresa May campaign in 2017. Speak to those in DC who know him and they will say: “You win if you follow Jim’s rules – they are proven.” May is the anomaly in that she did not follow the rules, and he was also not fully in charge. The people around May, Messina says, “didn’t understand anything about modern campaigns” and wanted to “go to war all the time and spent the entire time making the whole thing harder than it had to be.”

His regret – and he says it’s a mistake he’ll never make again – is that he took the job after a call from Crosby but never actually “sat down with her” beforehand to figure her out. “I didn’t do all the things I always do. I thought it would be just the same as Cameron. But it wasn’t, and it makes me incredibly rigorous in who I work for now.”

Goodbye to all that

The success of TMG – whether the campaigns are virtual boardroom, class action legal battles or vote-chasing on the campaign trail – is bound up with harnessing the power of data-driven strategies. It’s backed by experts from three companies which are soon to be augmented by a new venture capital company that will invest in these firms which form part of a Triple Crown of partners within the group.

These are Greenbrier Partners, one of Silicon Valley’s leading crisis management firms, Amplify Media, which is a media-buying firm that allows clients to target voters through a sophisticated mix of traditional and digital media, and Signal Media, which is a new legal firm that is aiming to “revolutionise” class action notices using media analytics. Above all, he is interested in assisting companies in using data-driven technology to outsmart excessive regulation.

Messina doesn’t see much difference between his political campaigns and working on corporate strategy – often of the “shit sandwich” variety – for Fortune 500 companies. One of his earliest clients after leaving the 2012 Obama campaign was Uber. “I loved that,” he says. “It felt like a campaign too. These tech companies really did have mini campaigns and we had to figure out how to tell the story of a new technology that was built for regulations that were written years before that technology. I help companies all around the world try to tell that story to regulators and governments.”

Reality TV

One of the things that comes across in talking to Messina is his raw passion – even obsession – with politics. He thinks that there is more glamour and excitement in politics today than when he was cutting his teeth on the campaign circuit. It comes as little surprise that he was a fan of George magazine, which tried to mix celebrity and politics,  before it folded after the 1999 death of founder John F Kennedy Jr.

I tell him that the Mace is about the business of politics, but it also takes some inspiration from George magazine and the idea that politics isn’t only of interest to the political class. I suggest that it is mainstream in the way that Wall Street and Liar’s Poker suddenly made the greed-is-good finance mantra the holy grail of careers in the 1980s and 90s. Messina agrees that there is certainly more interest today in what’s going on in Brussels, Washington and London, rather than just one country or capital.

“I loved George magazine. It was speaking to my lifestyle,” he says, before adding that it was ahead of its time in seeing the rise of celebrity in politics today. Not just Trump but all over the world. “People who are not traditionally in politics are coming into it, and for good or bad, it’s become more of a reality show.”

As a campaign manager, is it more difficult to win with candidates who aren’t well known? He replies that one of his biggest lessons learnt in 30 years of observing campaigns is that “everything is cyclical”. After the celebrity candidate, people typically want a more wonkish sort of candidate, like the Macron type. “We’re about to have that referendum in America, right? You have a celebrity Donald Trump versus the return to normal Joe Biden. What people want is a government that does its job and shuts up and doesn’t piss us off.”

I ask if he was already thinking of launching himself as a global election campaign strategist when he was working on the Obama campaign. “It certainly was not a plan. It certainly was a love of politics,” he says, adding: “I was pretty sure that I was done in American politics after running my dream race. I had done everything I wanted to do which is why my first call was to Cameron.”

Gun for hire

We increasingly live in a political age where big campaign managers resemble football managers who are hired to work for teams in countries where they are not native. In 2015, when working for Cameron, he found himself in the odd position of campaigning against his old friend David Axelrod, who had been his colleague in the Obama campaigns.

“It was weird because he and I were so close, and I learned about that in the press, which was maybe not the way that should have occurred,” Messina recalls. “It was not a pleasurable experience, I’ll say that”.

Did it lead to a fallout in terms of your friendship, or did you make up?

There is a pause down the line and for a moment I think I am losing the Zoom signal. “No, we really haven’t spoken.”

We change the subject to money. American campaigning is different from the UK in that in the UK we don’t have people like former New York Mayor Bloomberg spending $100m on TV ads to help Biden win just one state, the all-important Florida which Trump has to win in order to keep the White House. Is it difficult to roll out the Messina playbook without the vast amount of resources available to politicians in America? Does lack of money restrain your methodology?

“No, because a lot of what you spend money on in the US is TV ads,” he says. “And so it just means you spend using social media, using digital, using traditional canvassing. But you just have to do it on the cheap. Working on European campaigns is not a growth industry as far as making money [TMG made £246,000 from working on the referendum campaign]. It was really more a labour of love and loving to do it, because you guys just don’t have the money and it’s such a short amount of time.

“And, you know, in many ways, I think the British system is better. I don’t think you need a billion dollars to run a presidential campaign.”

4th October 2020