Beto O’Rourke’s Thursday hiring of Jeff Berman, a Barack Obama and Hillary Clinton veteran, is the latest step his presidential campaign has taken away from the insurgent energy of his Senate run and toward a more centrist and corporate strategic direction.

Berman, who is joining O’Rourke’s campaign as senior adviser for delegate strategy, is perhaps most well known for his expertise in the arcane system of delegate selection, which he used to help Barack Obama win the Democratic nomination in 2008. An often overlooked part of his record, though, is his stint at law and lobbying firm Bryan Cave, a position for which he was hired immediately after Obama’s presidential campaign. (As reporter Ken Silverstein remarked in Harpers at the time: “That was fast.”) According to the federal lobbying registry, between 2009 and 2011 Berman’s clients on behalf of Bryan Cave included the private prison company GEO Group; TransCanada, the company behind the Keystone XL pipeline; and SeaWorld, which was then owned by massive private equity firm Blackstone.

Many of these clients are ostensibly on the opposite side of many of the issues that O’Rourke is campaigning on. Take, for example, immigration, a central theme of O’Rourke’s presidential run: He launched his campaign in the border town of El Paso, Texas, railing against Donald Trump’s immigration policies and stating, “For more than 100 years, this community has welcomed generations of immigrants from across the Rio Grande.” Yet the GEO Group, for which Berman’s work (along with other lobbyists) made Bryan Cave $ 60,000 in 2010, has profited handily from its business of running private prisons, including immigrant detention centers. According to reporting from the Daily Beast, the GEO Group made large donations to Trump’s campaign and has only seen its revenue soar under the current administration, earning $ 2.3 billion in 2018, up from $ 2.18 billion in 2016. Berman’s work on behalf of the GEO Group was for “outreach related to the Bureau of Prisons budget allocation in the Administration’s FY2011 budget,” according to federal filings.

O’Rourke has also been trying to shore up his climate change bonafides in response to the young activist base of the Democratic Party. After being heavily criticized for breaking his pledge to not take money from fossil fuel executives during his Senate campaign, O’Rourke made the first major policy proposal of his presidential run a $ 5 trillion plan to combat climate change. And, after much pressure, O’Rourke again pledged to take in no fossil fuel money, promising to return donations already made to his campaign by fossil fuel executives.

Yet Berman’s past work on behalf of TransCanada between 2009 and 2011 puts O’Rourke’s newest staffer squarely on the opposite side of one of the most contentious climate issues during Obama’s tenure. As HuffPost reported when the Clinton campaign hired Berman, he and other officials from Bryan Cave made the firm $ 980,000 for their lobbying work for TransCanada.

According to the filings, Berman and others lobbied to help obtain “approval for Keystone Pipeline path through Missouri tracts” and later to “monitor climate change legislation and [push for a] presidential permit process for TransCanada Keystone Pipeline.” (Other lobbying objectives were listed, but they largely mirrored these two.)

Berman made his name in Democratic politics when, under his advice, Obama successfully navigated the delegate landscape in 2008 to win the presidential primary over Hillary Clinton; at the time, Berman was termed the “unsung hero of the Obama effort.” In 2016, Clinton hired Berman as her own delegate strategist. As BuzzFeed put it, the O’Rourke campaign’s hiring of Berman “indicates that O’Rourke plans to emulate Obama in building a technical campaign machine under the surface of what he hopes will feel like a movement.”

Berman’s hire follows O’Rourke bringing on Jen O’Malley Dillon, another Obama veteran and former executive director of the Democratic National Committee, as his chief of staff in March. Just a month after O’Malley Dillon’s appointment, the Bernie Sanders alumni who helped build O’Rourke’s Senate field operation, Becky Bond and Zack Malitz, split from the campaign, signaling a move away from the progressive, grassroots organizing strategy of his Senate run. In her statement on Berman’s hiring, O’Malley Dillon said that he was “one of the first people I reached out to when I came on board because delegate strategy is so critical to our overall strategy.”

O’Malley Dillon co-founded the consulting firm Precision Strategies, which has taken on corporate clients like Pfizer, Bank of America, and Facebook, as well as Democratic political clients like the DNC and Hillary Clinton’s 2016 campaign. Berman’s mixed record is standard for the wing of the Democratic Party that sees no issue with working toward progressive political ideals, while also advising the private sector. It seems to also be the wing that O’Rourke’s campaign is now firmly pivoting toward.

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