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There’s something about the Kennedys. It could be the name and accompanying brand; it could be a real current of talent and ambition that runs in the family; it could be the enormous hoard of inherited wealth that Joseph Kennedy’s progeny continues to benefit from. Whatever it is, there’s not a decade goes by that one of the Kennedys doesn’t throw his or her hat into the ring for some form of political office. This year, it’s Chris Kennedy, Chicago businessman and son of slain former attorney general and one-time presidential candidate Robert F. Kennedy, who in February announced his intention to run for governor of Illinois. Known as “the quiet Kennedy,” Chris Kennedy for decades ignored the siren song of politics that many of his siblings succumbed to, opting instead to become a successful businessman and philanthropist. Kennedy was best known as the head of Merchandise Mart Properties Inc., the company which owned Chicago’s Merchandise Mart, the massive office building and high-end retail space in the city’s downtown, as well as for developing Wolf Point, the Kennedy family’s real estate holdings in Chicago. Among other things, he also chairs the family’s investment firm Joseph P. Kennedy Enterprises and chaired the Board of the Trustees of the University of Illinois from 2009 to 2015. (The Kennedy campaign did not respond to a request for comment for this story.) Kennedy has maintained a progressive public image over the years. He donates to and is involved in a host of different charities. He runs a nonprofit that sells affordable groceries to low-income communities, citing a “commitment to social justice” inherited from his parents. That doesn’t mean Kennedy would bring much progressive change in Illinois, though. The state has seen two incredibly destructive years under current Republican governor Bruce Rauner, whose austerity politics brought about a protracted budget impasse and starved the state of sorely needed public funds. But Kennedy is far from an ideal candidate to take on Rauner’s reign of austerity.

Straddling the Line One of Kennedy’s major assets, he says, is his decades-long experience in the business world. “I’ve spent my entire life straddling the worlds of government and politics and the economy and business,” he told Chicago’s Daily Herald. This straddling appears to have instilled in Kennedy a steadfast belief in the healing power of the private sector. “As a twenty-year-old college student, I loved the idea of combining the best of the non-for-profit world with the best of capitalism to create a new type of entity — a social business,” he told the Chicago Tribune in discussing his hunger-fighting non-profit, Top Box Foods. “I loved the idea of conjuring up market forces to help alleviate social problems.” Kennedy stressed that his venture, which involved low-income and other families buying affordable groceries, was not a form of charity. “There’s a lot of dignity in our mission,” he explained. “[The] fact that it’s a hand up and not a handout is one of the reasons so many people like to work with us.” His words suggest that Kennedy shares conservatives’ suspicion of entitlement programs — or “handouts” — that provide material help to the poor as damaging to their “dignity.” To wit, Kennedy also appears to be a firm believer in the doctrine of centrist both-sidesism: that the problem with politics is that both major parties cater to their extremes, and what’s required is a politician who will bravely walk the middle of the road. “In the sixties and seventies, it was really a fight for the middle, that is . . . undecided voters, let’s say independent voters,” he told WGN Radio in 2014. “Today it’s all about trying to motivate the extreme ends of the spectrum, trying to get hardcore liberals or hardcore conservatives to turn out, and that creates a gulf where we need a bridge.” Of course, Democrats have employed this kind of rhetoric as justification for drifting further and further to the right — despite the fact that the general population is far more inclined toward “extreme” left-wing policies than many politicians and commentators will have you believe. Kennedy’s worldview appears to be one of reflexively tacking to the center at all costs — much like another recent Democratic politician for whom that tactic failed miserably. “Every now and then, somebody emerges as a voice for folks in the middle who seems like a practical and thoughtful public servant . . . and that’s not the run-of-the-mill politician,” he added in the interview. Kennedy clearly sees himself as just this type of politician who will reflexively occupy the center to appeal to this mythical demographic.

Bill Ayers Perhaps the clearest example of Kennedy’s potential governing style can be found in his time at the University of Illinois, whose board of trustees he chaired from 2009 to 2015. During that time, Kennedy repeatedly rolled over — or even tacked to the right — at the slightest hint of controversy. Kennedy’s emails, some of which were released in past document dumps and others recently obtained through a Freedom of Information request, give some of the behind-the-scenes details of these incidents. First was the Bill Ayers episode in 2010. Ayers, a former Weather Underground member-turned-respected education professor at the University of Illinois at Chicago, became a political football when the McCain campaign used his vague acquaintance with Obama to smear the latter in 2008 as “palling around with terrorists.” Right-wing commentators took turns demonizing Ayers for acts he may or may not have committed forty years earlier. Two years later, Ayers was due to receive the largely honorific title of professor emeritus, given to “those individuals who have contributed measurably” to the university (rather than being a referendum on everything an individual had ever done in his or her life), according to the UIC faculty handbook. As per the university’s guidelines, emeritus nominations are approved by the department, the college dean, the chancellor or provost, and the president, before being approved by the board, which had never in living memory rejected emeritus status for a retiring professor. Ayers’s selection had already been approved by multiple university officials before it made it to the board, which typically acted as a rubber stamp. Kennedy, however, led the board in denying Ayers the title, on the basis that a book Ayers had helped write in 1974 while part of the Weather Underground appeared to be dedicated in part to Sirhan Sirhan, the man who had killed Kennedy’s father. Ayers says he was told by those in the know that Kennedy had based his decision on Sean Hannity segments like this one. The faculty senate criticized the decision. One professor told the Tribune she was “shocked,” given that Ayers had “a forty-seven-page resume of academic accomplishments.” Ayers told Newsweek at the time that he “felt very sad” that Kennedy and his family had to “revisit” the incident, but claimed the inclusion of Sirhan was not his decision. He explains that the page in question — a wall of hundreds of names with the dedication “to all who continue to fight, to all political prisoners in the US” — was drawn up by an artist and that Ayers didn’t know most of the names on the list. Moreover, he says, the page was meant as a criticism of the criminal justice system, the idea being that “all prisoners are political prisoners.” Ayers says the board never got in touch with him for an explanation before voting. “What would they say if they got in touch with me?” he says. “Come in and defend a book you co-wrote in 1974 when you were on the run from the FBI?”

James Kilgore Next was the case of James Kilgore, an adjunct professor at UIC in Global Studies and African Studies who the local News-Gazette revealed in 2014 had been a former member of an admittedly bizarre 1970s leftist revolutionary group, the Symbionese Liberation Army. After twenty-seven years on the run, Kilgore had been convicted for his part in a 1975 bank robbery that had left one person dead. He served a six-year sentence, during which time he was a model prisoner, was paroled in 2009, and soon after got a job at UIC, where his wife worked as an associate professor of gender and women’s studies. Kilgore eventually served his sentence, left prison remorseful for his actions, and got a job. But the university didn’t see it that way, and after the paper’s story, the administration cancelled his contract in early 2014 without reason, despite his glowing performance reviews. In May 2014, Kennedy told the News-Gazette that Kilgore was “a domestic terrorist bent on overthrowing the government by targeting the murder of police,” despite the fact that it had been more than three decades since his crime. “We’re not reacting to public pressure,” he said, and denied that it was an issue of academic freedom because “this is an hourly employee who doesn’t have tenure.” (One dissenter emailed Kennedy that he was “disturbed” by this “inane statement,” because of two-thirds of the country’s faculty were part-time, and “academic freedom is a right awarded to all faculty”). Kennedy’s emails suggest public pressure was involved. The same day Kennedy’s comments were printed by the News-Gazette, Kennedy checked with the president of the university’s alumni association whether or not alumni were supportive of his actions. She told him that “most callers are opposed to retaining [Kilgore],” with a few threatening to stop donating. In an earlier email to University of Illinois president Robert Easter about the Gazette story, Kennedy had noted that much of the university’s funding came from state taxes, which meant the university “need[ed] to be sensitive to tax payers.” “I think they are going to be offended by the notion that their taxes are going to support the lifestyle and career of a fellow who tried to overthrow the US government and targeted police officers and innocent victims for killings,” he said. “These comments may reflect my own cultural views and personal prejudices,” he added. “I freely admit to being influenced by these forces.” Kennedy registered his concern that if the university didn’t “reflect the values of the state,” angry taxpayers would deprive the school of funds. The email also demonstrated some decidedly un-progressive thinking on Kennedy’s part when it came to the issue of criminal rehabilitation. “If someone breaks the law and serves his sentence, he should be able to move forward with his life. Our country should be a land with second chances and redemption,” he affirmed. “Having said this, I am still uncomfortable with the notion that, that second chance should come from public support,” he continued. “Clearly we need to help people transition from the criminal justice system back into society as productive members, but I don’t think we need to necessarily provide lifetime employment.” So to be clear, Chris Kennedy believes ex-convicts should be rehabilitated and reintegrated into society, but not if it involves any “public support,” or if it involves them being hired by a government entity. Kennedy went on, complaining that, “given the enormous attention that Ayers received,” it was “incredible” that neither he nor the board were informed that “the University was home to another such ex-terrorist.” Complaining that the campus was plagued by a lack of “civility,” Kennedy offered that “we shouldn’t be so surprised” given that “we have held up to the students as examples people like this fellow.” Kennedy later forwarded this email to a producer at the O’Reilly Factor with the message “FYI,” at which point he was informed the show was “planning on doing a segment on Kilgore.” It’s not clear if Kennedy was already aware of this when he sent the message.