Cheryle Jackson, the head of the Chicago Urban League, announced on Monday her intention to run for the U.S. Senate seat that Barack Obama gave up when he was elected President.
I met Jackson, now 44, in the spring of 2003 when I was writing a profile for Chicago magazine of then-Gov. Rod Blagojevich. Jackson was Blagojevich's communications director at the time.
Before becoming Blago's press flack, Jackson had been Amtrak's regional vice president for communications and government affairs. David Mendell, then a Chicago Tribune reporter, wrote in December 2002 that, according to his sources, Blagojevich "specifically sought an African-American woman for the post that represents the administration to the media [because] the overwhelmingly Democratic vote totals from the black community in Chicago and the south suburbs were key to their election victory."
Jackson was impressive, strong willed and minded, and, initially, difficult.
After I called her to request face-to-face interviews with her boss, she told me, during a telephone call on May 23, 2003, that the level of access I got to Blago would depend on his getting the magazine's cover. I had also asked for an interview with the state's new First Lady, Patti Blagojevich, and Jackson reiterated that access would have to wait on an assurance that my Blago profile would run on the cover. She even had the cover shot set in her mind. She wanted her boss to pose with the cast of the soon to be released Barbershop 2: Back in Business. She explained that there would be a bill signing on the set of the movie.
A week or so later, she left a message on my voice mail accusing me of calling people close to the governor and misrepresenting myself by telling them that I was given their names and contact info by Jackson or by "the governor's office." I told her I would never do that. "I have [a long list] of names," I told her when I reached her by telephone, "and I'll call whom I want."
She backed down and we agreed "to put this behind us." She also dropped the cover boy demand. When the piece was published in the November 2003 issue of Chicago the cover was "the 2003 Dining Awards" with a line running across the top, "Governor Sunshine: the Blagojevich Story."
After that, Jackson never attempted to stymie my progress in any way. She set up face to face interviews with Blagojevich in his office in the State of Illinois Building that July and August.
She helped me arrange interviews with a few key people, including Patti, and Lon Monk, then Blago's chief of staff, who was indicted in the federal corruption case against his former boss.
She called ahead to help me land an interview with Ed Vrdolyak, for whom Blago worked early in his career. She also urged me to talk to David Wilhelm and told me that she intended to call Wilhelm, who was Blago's 2002 campaign chair, transition adviser, and member of his "kitchen cabinet," and tell him to "take my call."
When I interviewed Wilhelm that August, he told me that the three people closest to Gov. Blago were Cheryle Jackson, Lon Monk, and Bradley Tusk, then Blago's deputy governor (now running New York's Mayor Michael Bloomberg's reelection campaign).
According to Crain's political columnist Greg Hinz, David Wilhelm will serve Cheryle Jackson as a "special adviser" in her 2010 run for the Senate seat. Wilhelm had also run Bill Clinton's 1992 campaign. If Jackson was taken with Blago, she was not alone. When I interviewed Wilhem in 2003, he described Blago as "certainly among the most gifted natural politicians. ... Same ability to light up a crowd or a room that Bill Clinton has."