Best Former Paratrooper and Cubs Prospect Running a State Office

Secretary of State Jesse White

Critics' Picks

Who doesn't like Jesse White? There are probably a few people, but they can't beat him at the polls. White hasn't had a serious challenge since being elected secretary of state in 1998; in his most recent reelection bid, in 2010, he received more than 2.5 million votes, the most of any candidate for any office in Illinois. White's fascinating biography doesn't hurt his cause: he had a stint in the Cubs' minor-league system; he served as a paratrooper in the U.S. Army; he founded the Jesse White Tumblers to help at-risk kids and taught for three decades in the Chicago Public Schools. What's less well known is that White is also a wily Chicago politician with the clout that comes from controlling hundreds of public-sector jobs. To those who prove their worth in his 27th Ward organization, White is unshakably loyal, which is why Derrick Smith was sent to the state legislature even after he was fired from a city job for ethical lapses—the same Derrick Smith who was subsequently indicted for bribery. But beware to those who oppose or betray White—you'll be taken out. "We play hardball," White once said to me—in the nicest, most charming way possible.