Politics & Policy

The Chicago Way

President Obama walks with Eric Whitaker while golfing on Martha’s Vineyard.
Obama’s coterie of insiders is worth a closer look this time around.

Every president comes to Washington with a coterie of outside advisers, friends, and fixers they’ve picked up during the course of a career. Eventually one or more of them becomes controversial. Richard Nixon had Bebe Rebozo. Jimmy Carter had his brother Billy and Bert Lance. Ronald Reagan had Mike Deaver. Bill Clinton had many trailing after him — they became the menagerie implicated in Whitewater and Monicagate. But Barack Obama’s inner circle has almost completely escaped close scrutiny since he became president. That may be about to change, and the rich cast of characters making up Team Obama merits further attention.

A new biography of Obama by Edward Klein called The Amateur has rocketed to the No. 1 slot on the New York Times bestseller list. Among its explosive allegations is that after videos of Reverend Jeremiah Wright’s anti-American sermons surfaced in the 2008 campaign, a close friend of Obama’s and a fellow member of Wright’s church named Eric Whitaker approached the reverend. In a taped interview with Klein, Wright said Whitaker offered him — via e-mail, through an intermediary — $150,000 to stop preaching and appearing in the media until after the election.

#ad#After Wright turned the offer down, Barack Obama set up a private meeting with him to urge him not to speak publicly during the campaign. Secret Service logs document that it took place, writes Klein. But Wright refused to cooperate, and the meeting ended in frustration for Obama.

Efforts to discredit Klein’s book by Team Obama went into overdrive after the revelation. Certainly, Klein made errors in a previous book attacking Hillary Clinton, and his occasional sloppiness in his current book isn’t up to the standards of a New York Times Magazine editor, which he used to be. But Klein says he has tapes with Wright to back up his account, which also includes the charge that Obama relied on Whitaker to find a replacement preacher once Wright was dropped from an Obama event.

Whitaker’s role in Obama’s world is important because, as Patrick Brennan has pointed out on National Review Online, “it’s almost impossible to overstate how close Whitaker is to the president.” He’s been a friend of and fundraiser for Obama for nearly 20 years and has joined the first family on every summer and Christmas vacation since 2008. Politico reported in 2009 that Whitaker had become “a kind of gatekeeper and spokesman for Obama’s inner circle.”

Whitaker has also been involved in Illinois’s always shady politics. He became the state’s top health official in 2003 when he was appointed by then-governor Rod Blagojevich, now a resident of federal public housing after his conviction in 2011 on corruption charges. As the Chicago Sun-Times reported in 2008, Obama gave Whitaker “a ‘glowing’ reference to Tony Rezko,” who interviewed him for the job. Rezko, a friend of Obama’s for two decades and a top fundraiser for both Obama and Blagojevich, is also now in federal prison on corruption charges. Prosecutors alleged that Rezko engineered pay-to-play schemes with Blagojevich to help allies secure jobs. Neither Obama nor Whitaker was implicated during Rezko’s trial.

You might recall the name of Tony Rezko from the 2008 campaign.

Rezko was involved with Obama in a controversial 2005 land deal in which Obama bought a $1.65 million home on the same day that Rezko’s wife bought the plot of land next to it from the same seller for $625,000. Obama has strenuously denied suggestions that the same-day sale enabled him to pay $300,000 under the house’s asking price because Mrs. Rezko paid full price for the adjoining lot — a portion of which Obama subsequently purchased — but he admitted the whole deal was a “boneheaded” mistake.

One of Whitaker’s duties as Illinois’s health director was to oversee the scandal-wracked Illinois Health Facilities Planning Board. Under Blagojevich, that board was used to extract kickbacks for state contracts to expand hospitals, which financially benefited Rezko and his associates who controlled the board. During a subsequent investigation, Whitaker denied knowing anything about the wrongdoing, saying he wasn’t involved in the board’s day-to-day operations.

#page#Whitaker left his job under Blagojevich in 2007, and is now executive vice president of strategic affiliations at the University of Chicago Medical Center. He is in charge of its Urban Health Initiative, which this May won a $5.9 million federal grant. As Brennan reported, the UHI “is a microcosm of Obama’s small and incestuous corner of Chicago’s elite politics.” Michelle Obama, as an executive at the University of Chicago Medical Center, created and developed the UHI program until she took a leave of absence during her husband’s 2008 campaign. Valerie Jarrett, now perhaps the most powerful staffer in Obama’s White House, approved the program as chairman of the medical center’s board, and Obama strategist David Axelrod was hired to promote its minority-outreach efforts.

The program itself is controversial, with several medical groups claiming its efforts to shift poor patients to local clinics and away from hospitals such as the University of Chicago’s amount to a deliberate effort to dump uninsured and unprofitable patients onto clinics so that the hospitals can treat insured patients instead.

#ad#Fran Eaton, the editor of the conservative blog Illinois Review, says the Whitaker–Reverend Wright controversy is fascinating because it exposes the cozy world of the “Chicago Way” that brought Obama to power. Everyone in the drama is involved in the Richard Daley machine. Valerie Jarrett and Michelle Obama first met while working for then-mayor Daley. Obama ran for the first time for the Illinois state senate unopposed after Daley-machine lawyers knocked every one of his primary opponents off the ballot by successfully challenging the validity of their nominating petitions. Rahm Emanuel, the current mayor of Chicago, was elected to Congress in 2002 with Daley’s help and went on to serve as Obama’s White House chief of staff from 2009 to 2010.

None of this suggests Barack Obama was directly involved in the seamy underworld of the Daley machine — on the contrary, he was always protected from any hint of corruption because he was clearly being groomed for higher office. But it certainly demonstrates just how little scrutiny Team Obama got over its Daley connections during the 2008 campaign and how far removed the “hope and change” theme of his campaign was from the rough-and-tumble reality of Chicago politics.

John Heilemann, co-author of a definitive work on the 2008 election called Game Change, writes in a new piece in New York magazine that for “anyone still starry-eyed about Obama” the 2012 campaign will disabuse them of that notion:

The months ahead will provide a bracing revelation about what he truly is: not a savior, not a saint, not a man above the fray, but a brass-knuckled, pipe-hitting, red-in-tooth-and-claw brawler determined to do what is necessary to stay in power — in other words, a politician.

If the mainstream-media journalists who spent so little time in 2008 looking into the Daley machine that Barack Obama sprang from want to do more due diligence this time, they could start with a closer look at Eric Whitaker and the rest of Obama’s inner circle. It’s probably a much richer mine of stories than any investigation of Mitt Romney’s Bain Capital days or Ann Romney’s obsession with expensive horses is likely to provide. 

— John Fund is the national-affairs columnist for NRO.

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