Mark Penn is a veteran pollster and political strategist. Mark Penn has a plan.

According to Penn, in a coauthored New York Times op-ed yesterday entitled “Back to the Center, Democrats,” the party’s only pathway back to political relevancy is “to move to the center and reject the siren calls of the left, whose policies and ideas have weakened the party.” Apparently, a candidate who said one of the Democrats’ most cherished and long-held policy goals will “never, ever come to pass,” racked up the endorsement of a long list of GOP neocons, and got beaten by a guy who made his opposition to a widely hated free-trade deal that she helped create a regular part of his stump speech was too left-wing. Go figure.

Penn’s advice may not make any sense, but the fact that he’s the one giving it does: Penn’s chief claim to fame is as the architect of Bill Clinton’s mid-nineties move to the center.

Penn’s achievements were considerable: he allowed Clinton to gut welfare, pass a crime bill that destroyed black communities, deregulate the financial industry, ban same-sex marriage, and very nearly privatize Social Security. Time magazine at the time called Clinton’s post-re-election policies “a wild, drunken Republican dream.”

Bill wasn’t the only Clinton Penn would offer his services to. In 2007-08, Penn served as the chief strategist to Hillary Clinton’s campaign, an inevitable-victory-turned-desperate-comedy-of-errors almost on the scale of the 2016 edition. Penn, to whom Clinton would end up owing $2.3 million for his services at the end of the campaign, could proudly take a bow for helping torpedo her chances.

1. He thought Democratic primaries were winner-take-all while running Hillary Clinton’s 2008 campaign.

One of Penn’s many contributions to the result was running Clinton’s campaign on the basis that Democratic primaries are winner-take-all. As anyone familiar with Democratic nomination campaigns — and certainly anyone being paid to run one — ought to know, they are not. Rather, candidates win a share of the delegates proportional to their share of the vote.

Penn apparently didn’t know this.

As Time reported in 2008, at a strategy session the year previous, Penn confidently predicted that Clinton would secure the nomination with an early win of California’s 370 delegates. Longtime Clinton confidante Harold Ickes was not impressed. “How can it possibly be that the much vaunted chief strategist doesn’t understand proportional allocation?” he reportedly remarked.

To be fair to Penn, his plan may simply have been for Clinton to win 100 percent of the vote, a feat that’s theoretically possible, though one not even Kim Jong Il was able to pull off during his reign.

Despite the fact that this strategy was based on a basic ignorance of how Democratic primaries work, remarkably, it remained in place, with the campaign focusing on big state victories. Needless to say, things didn’t work out.

2. He lobbied for a trade deal at the same time Clinton was opposing it.

While running Clinton’s 2008 campaign, Penn held the dual responsibility of being CEO of Burson-Marsteller, a global public relations firm that represented drug companies, a tobacco firm, Countrywide Financial (which would soon gain notoriety for helping to detonate the global economy), and the Little Private Military Contractor that Could, Blackwater. Clinton didn’t make Penn leave the firm, and he had no inclination to do so.

This was despite — or maybe more accurately, because of — the colossal conflict of interest it represented. As Penn wrote in a private blog for his colleagues:

I have found the mixing of corporate and political work to be stimulating, enormously helpful in attracting talent, and helpful in cross-pollinating new ideas and skills. And I have found it good for business.

Penn’s extra-curricular activities proved to be his undoing when it came out that one day before Clinton had announced her opposition to a union-opposed free-trade deal with Colombia, Penn had met with Colombian officials to promote the deal. He had to publicly apologize and was swiftly demoted, while Clinton scrambled to reaffirm she would continue to oppose the deal.

3. He advised Clinton to embark on a race-baiting strategy.

Clinton’s 2008 campaign was a doozy. Not only did the entire nomination contest quickly turn ugly, but as Clinton’s chances started slipping away, it was also the occasion for one of the uglier race-baiting campaigns in recent memory.

It’s not clear how much of this can be chalked up specifically to Penn (after all, it’s not exactly the first time a Clinton decided to pull out the dog whistle). But Penn certainly tried his hardest to get his boss to use Obama’s background against him.

Way back in a March 2007 memo, Penn, who believed Obama was “unelectable except perhaps against Attila the Hun,” suggested that Clinton jump on his “lack of American roots.” Reacting to articles looking at Obama’s boyhood in Indonesia and his formative years in Hawaii, which he said were “geared towards showing his background is diverse, multicultural,” Penn wrote: “Save it for 2050.”

He went on to charge that Obama’s “roots to basic American values and culture are at best limited,” and that he couldn’t “imagine America electing a president during a time of war who is not at his center fundamentally American in his thinking and values.” To highlight this, Penn suggested that each of Clinton’s speeches contain a line that “you were born in the middle of America to the middle class in the middle of the last century,” that she talk about the “deeply American values you grew up with,” and to “own ‘American’ in our programs, the speeches and the values” because “he doesn’t.”

Later, Penn would urge the campaign to use Obama’s association with Jeremiah Wright against him as the McCain campaign would later do, writing: “Won’t a single tape of Wright going off on America with Obama sitting there be a game ender?”, and that “twenty years sitting there with ‘Goddamn America’ would make him unelectable by itself.”

4. He gave Clinton lots of other terrible advice.

All of this sterling counsel led Penn to receive by February 2008 what Mike Madden estimated as 9 percent of Clinton’s $138 million fundraising haul. But Penn’s multi-million-dollar advice wasn’t just limited to misunderstanding basic primary rules, using the campaign as his personal influence-peddling machine, and advising his candidate to get subtly racist. He also:

• told Clinton that “we are more Thatcher than anyone else — top of the university, a high achiever throughout life, a lawyer who could absorb and analyze problems,” holding up Thatcher as the “best role model” for the “tough single parent” tone Clinton should convey.
• proposed a “viral campaign among moms” about “your sons and daughters believing that they too can be president” that would involve “a video with celebrities … saying what they would do if president.”
• putting literal “Hit to Restart 21st Century” buttons “everywhere,” which Penn predicted would “appeal more to younger guys.”
• advising Clinton not to apologize for the Iraq War because it would be a “sign of weakness,” ultimately leaving her vulnerable to attacks from both Obama (who publicly spoke against it) and John Edwards (who did apologize for his vote).

Beyond this, it’s somewhat amusing how much of Penn’s advice from Clinton’s failed 2008 campaign was recycled in her 2016 run, from her use of celebrities to the portrayal of her as the “most qualified” and “most experienced” candidate in history. Even Clinton’s campaign slogan, “Breaking barriers,” seems to have come from Penn’s memos (Penn, ca. 2008: “Our positioning: experienced leadership you can count on, someone who can break barriers for you”).

5. Everyone from the campaign but the Clintons seems to hate Penn.

Given all this, it’s perhaps no surprise to find that Penn was widely blamed within the campaign for Clinton’s defeat.

Of course, there’s never a shortage of fingers being pointed in the wake of a failed campaign, particularly one as reportedly full of infighting as Clinton’s was. Still, there appears to be a strong consensus that, after Clinton herself, Penn was the chief person responsible for sinking her campaign.

“Mark Penn has run this campaign,” Ickes said in February 2008. “Besides Hillary Clinton, he is the single most responsible person for this campaign.” Ickes went on to say that Penn insisted on being referred to as the “chief strategist,” that he “shaped the strategy of the campaign” and “called the shots,” and “dominated the message in this campaign.” That message, of course, was that Clinton was the experienced, well-credentialed insider, making her easy pickings for Obama’s portrayal of himself as the outsider change-agent.

Clinton’s team reportedly hated Penn and considered him “a detrimental force whose perniciousness was amplified by his inexplicably tight bond with the Clintons.” Six years later, numerous campaign operatives and former staffers refused to work on Clinton’s 2016 campaign if he was involved.

Clearly, Penn is highly qualified to lecture the Democrats, as long as his advice is about how to sink once promising election odds and lose. You can’t say the same thing about his co-writer, though: Andrew Stein endorsed Trump.