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Dart and chief deputy sheriff Kevin Connelly leave a house in Englewood after serving an eviction notice.
In the movies, the sheriff’s gut hangs over his belt, his jaw bulges with tobacco, his leather holster creaks, and he says BINGO! after he spits. It’s a cliché long discarded—these days, the big-city sheriff often looks and acts more like a ward heeler than the clichéd good ol’ boy. But vestiges of the old lawman stereotype remain: the tradition of the sheriff as a former cop with a reputation rooted in toughness.
Enter Dart. Though he was a prosecutor for a time and cochaired an Illinois prison oversight committee, he was never a police officer. Never carried a gun. Never made an arrest.
He’s never been accused of being a wimp—as an assistant state’s attorney, he was relentless in rooting out and prosecuting corruption in the Ford Heights police department. Beyond that, however, his background seems more community do-gooder than tough-guy top cop: tutoring kids at Cabrini-Green, starting a flag-football league for children he felt were too young to be in pads, state representative from a ward that was mostly African American. Even when he did ascend to the Cook County sheriff’s post, he shunned many of the office’s trappings: He has no driver, no security detail. He doesn’t plaster his name on every order, every placard. When summoned in November to testify before Congress about his eviction moratorium, he packed his three staffers in his Chevy Tahoe and drove to Washington, D.C., to save the county the airfare. He rides his bike to school each morning with his son.
“Dart is a very intellectual guy,” says Russ Stewart. “He’s not the big, bruising type of sheriff you customarily envision in the office.”
He’s aware that he’s a different breed. “That’s been reinforced to me several times,” he says. “When I meet with other sheriffs, say from Downstate, it’s abundantly clear that I’m not the norm. They laugh about it. I laugh about it.”
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Raised in Beverly, Dart and his wife, Patricia, along with their four children, live two miles from Dart’s parents. Early on, he felt drawn to politics—to the dismay of his father, who, as a lawyer in the corporation counsel’s office of Richard J. Daley, advised against that kind of career.
“He thought I’d have a much more satisfying life not having to deal with the despicable people you sometimes found in politics,” Dart says. “He thought it would be easier just to practice law and make some money.”
After earning a bachelor’s degree in history from Providence College, Dart returned to Chicago to attend law school at Loyola University. In 1987, the freshly minted lawyer landed a job as an assistant Cook County state’s attorney. Over the next five years, he prosecuted hundreds of felons, and he headed the Ford Heights corruption investigation, which resulted in the conviction of police chief Jack Davis and five other officers on charges of extorting bribes from drug dealers and abetting them in their distribution of heroin and crack.
Dart might have continued in that role, but in the early nineties, Jeremiah Joyce, a staunch ally of Mayor Daley, resigned from the state senate. Dart, who lived in Joyce’s 19th Ward (as did Sheahan), was appointed to fill the vacant seat. A year later, he ran for a seat in the Illinois House from the 28th District, a diverse swath of the South Side that included parts of Roseland, Pullman, Morgan Park, Mount Greenwood, Calumet Park, and portions of Blue Island. Dart was a long shot. His opponent, Nelson Rice, was an African American incumbent in a district that was more than 60 percent black.
But Rice was ailing and unable to campaign actively. Dart, by contrast, was tireless. “I just went everywhere,” he says. “I knocked on door after door. I also had some credibility within the African American community from things like tutoring at Cabrini-Green.”
Still, he recalls, “my father was so sure I would lose that he called me on election night to console me. I said, ‘Well, Dad, there are still some votes out there. Let’s see what happens.’ I ended up winning by a few hundred votes.”
In Springfield, Dart developed a reputation as a reform-minded legislator and a royal pain in the ass—mostly for the extraordinary number of bills he proposed. Unlike most members, he did not have a lucrative outside job, which left time to focus all his considerable energy and attention on researching and proposing new legislation. “If you pulled up the number of bills I introduced, you’d probably find yourself laughing,” Dart says. “I’d find myself reading something, a book or an interesting magazine, and I’d rip it out, research it; then I’d introduce a bill on it.”
Thus, he sponsored bills on everything from hog farming to the designation of Drummer silty clay loam as the official state soil. Much of his legislation went nowhere (the soil bill did pass in 2001), but he did have successes—namely in his efforts to bring sweeping changes to the Illinois Department of Children and Family Services.
“He was different from other reps,” says Franks. “He read everything. He worked so hard. He took his job very seriously. He was not what you’d consider the typical pol.”
He was a good interview—and telegenic. He often wound up on one of the cable television programs produced by the office of the Illinois House of Representatives speaker, Michael Madigan. One of Madigan’s staffers saw more than just an articulate policy wonk. Patricia McAdams married Dart in 2000. “There were no airs about him,” she says. “And he knew everything. People could never say a bad thing about him.”
The longer he spent in the General Assembly, however, the more he felt his returns diminishing. His bills were sometimes ignored. “After a while, I was spending more time fighting my own party than accomplishing what I wanted,” he says. “I wasn’t being productive anymore.”
At least one big positive came out of those tough times. Among the legislators with whom he commiserated was a skinny, thoughtful, well-spoken state senator named Barack Obama. “That’s how we got to know each other,” says Dart, who considers Obama a friend. “We would meet and talk about” their shared tribulations. The two partnered on child-welfare reform and criminal justice, and later Dart would help run Obama’s unsuccessful campaign against Congressman Bobby Rush.
Dart left the legislature in 2003, and after an unsuccessful campaign for Illinois state treasurer (he lost to the Republican incumbent, Judy Baar Topinka), he was appointed to serve as the chief of staff to Cook County sheriff Michael Sheahan. In 2005, he was deciding his next move—“As much as I enjoyed what I was doing, it wasn’t something I saw myself spending the rest of my life doing,” he says—when Sheahan abruptly decided not to run again. The timing, just as the Democratic Party was choosing its slate of candidates, was auspicious.
Sheahan immediately endorsed Dart, a move that infuriated Rush, who believed Sheahan was trying to shut out other possible candidates, including black and Latino hopefuls. (Rush did not respond to interview requests from Chicago.) In March 2006, Dart won the Democratic primary election by a wide margin, beating two former Cook County Jail officials, Sylvester Baker and Richard Remus. He won the general election in November 2006.
During his 16-year tenure, Sheahan had been praised for some of his early reforms, such as creating a boot camp for first-time offenders. But his tenure was also dogged by controversy, including chronic overcrowding in the jail and numerous allegations of abuse of inmates by guards.
Dart quickly instituted a number of reforms. He raised the hiring standards for Cook County guards, installed new technology in the Cook County Jail, and created a number of programs for women inmates, including a “bright space,” where soon-to-be-released women could spend time with their children in a comfortable, homelike environment. “The challenge for Tom is that he inherited an office where it’s hard to change the culture, and I would argue it’s a culture that needs changing,” says Quigley. “But I give him high marks for trying. I think he’s a nice guy; I think he’s a tough elected official. I think he’s in a tough spot.”
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Photograph: Chicago Tribune photo by Nancy Stone
2 years ago