Defending the Deplorable

Locals and outsiders alike have enjoyed peering into the viscous melting pot of politics and crime in Chicago. From Capone to “machine” politics to battles between the feds and the city, it’s not easy to mix into this bubbling brew without getting yourself cooked. Four of Chicago’s criminal defense attorneys speak frankly about what defending the deplorable is really like.

Jeffrey E. Stone, a partner with the Chicago office of McDermott Will & Emery, got an early taste of criminal trial work while at Harvard Law School by second-chairing a trial led by notable criminal defense attorney Alan Derschowitz. Stone, who now concentrates on white-collar criminal defense work as head of the trial department at McDermott, represented in the early 1990s a man who was half of a notorious father-son bank robbery team.

Apparently inspired by the Patrick Swayze/Keanu Reeves movie Point Break, John T. Hunter and his son, John T. Hunter Jr., were accused of robbing 35 banks in the Chicago area while wearing masks featuring U.S. presidents. “There was a lot of evidence against our client,” he says. “We fought incredibly hard on this case, and while our client was sentenced to a long period of incarceration, I’m very proud of the work we did,” says Stone.

The least palatable part of his job? “I don’t like losing,” says Stone. “Corporate lawyers often win because the deal closes and everyone’s happy. As a defense lawyer, the wins are terrific, but the losses stay with you forever.”

Stone strongly eschews the “D” (for deplorable) word when referring to his clients. “Our system of justice is founded on the premise that everybody is entitled to a fair and meaningful defense,” he says. “Just because the government describes the crime or the individual as deplorable, that’s not the end of the inquiry. If saying someone is deplorable was all that was necessary, there’d be no need for a trial.”

Vincent J. Connelly, a partner with Mayer, Brown, Rowe & Maw, views the practice of criminal law as a vigorous but fair fight between two opposing teams. The former chief prosecutor for the U.S. Attorney’s Office for the Northern District of Illinois switched to criminal defense in 1987. “It’s really like baseball players,” he says. “The game remains exactly the same; you just happen to be on another team.”

Connelly also handles white-collar criminal defense work, in which appearances can be deceiving. He recalls a day when he realized how working with two types of clients gives him insight into the intricacies of human nature.

“I had a situation where I was representing a fellow accused of engaging in extortion to collect illegal gambling debts,” Connelly says. The client confided from his cell that he wouldn’t testify since the accusations against him were essentially true. Connelly left the jail to meet with a company CEO accused of engaging in bid rigging. Neither client testified, but only the defendant accused of extortion was convicted.

“It was a wonderful juxtaposition,” he says, mulling over which of the two defendants the public would guess as more likely to lie on the stand to save themselves. Connelly says he wonders if most people would “choose the person accused of physically intimidating people over gambling debts or the CEO of a company.”

The Chicago native found himself drawn to criminal law while attending law school at the University of Chicago. “There’s a reason people are able to sell novels and TV shows about criminal law,” he says. “It’s so much easier to grasp and remember facts surrounding criminal cases than something obscure in the tax code.

“I only wanted to do one thing, which was to try cases,” says Dan Webb, the much-sought-after litigator who was elected chairman of Winston & Strawn in 2006. His roster of clients includes General Electric, Phillip Morris and former Gov. George H. Ryan. Not bad for a small-town Illinois kid who never graduated from college. Three years in, Webb used his already well-honed persuasive powers to convince the dean of Loyola University Chicago School of Law to admit him before he graduated.

The rest is legal history: Webb went on to become U.S. attorney in Chicago, where he successfully prosecuted Adm. John Poindexter in the Iran-Contra affair and spearheaded the “Operation Greylord” investigation into Cook County judicial corruption.

One of Webb’s few violent criminal cases involved a famous Chicago author and attorney, Scott Turow, in a famous Chicago-area case—the 1983 murder of 10-year-old Janine Nicarico. Alejandro “Alex” Hernandez was on death row for the little girl’s murder and as Webb and Turow, working pro bono, readied for trial after a successful appeal of the original conviction, the district attorney dismissed the case. “We got Alex off death row and he’s a free man today,” says Webb.

“Whether violent or white collar,” Webb says, “criminal cases that involve a person’s freedom and their future have enormous stakes. If you’re successful, the sense of accomplishment and victory is enormously rewarding.”

William H. “Bill” Hooks, founder of Hooks Law Offices, looks and sounds like a guy you’d want on your side when trouble strikes. The brawny former Marine Corps lieutenant colonel worked as a prosecutor for the Corps but ultimately switched to defense—because he felt it was a tougher job. “I liked the idea of using my own ingenuity and creativity to defend someone against an entity,” he says. Hooks uses military analogies when describing his Chicago law practice; cases are “battles” and defendants are “surrounded by the enemy.” His clients range from the indigent to high-profile media cases, like the unique technical appellate issue related to the 2003 “E2” nightclub tragedy, in which 21 people were trampled to death and dozens injured. It was speculated at the time that people panicked and stampeded to the exits after police used pepper spray to break up a fight. Hooks was not involved in the wrongful death suit, but he represented one of the nightclub managers to appeal a judge’s finding that the manager violated the judge’s prior order not to re-open certain sections of the club.

Few would mess with Hooks in or out of court, even though he is charismatic and affable. A judge once appointed him to represent a defendant who allegedly made threats against a senior public defender. Hooks’ new, burly client greeted him with a smile during their first meeting. “I told him that if he thought he was going to spread rumors about doing something to me, [that] it would be a bad thing to do,” he says. “After that, we were OK.

“I like defending the underdog,” he says. “I like looking in the face of people that feel nobody’s ever had any faith in them, and giving them the feeling that someone has faith. It doesn’t produce very much money. We’ll never be [famous Chicago attorneys] Corboy or Clifford,” he says with a laugh, “But we’ll have as much fun.”