Jack Ryan married actress Jeri Ryan (Seven of Nine, Star Trek Voyager) in 1991. They divorced in 1999. He retired from Goldman Sachs in 2001 with enough money (hundreds of millions) to run for the Illinois Senate as a Republican in 2004.
In the middle of the Senate race against Democrat Barack Hussein Obama II, the Illinois GOP leadership demanded Ryan drop out due to some scandalous charges made in his divorce. The GOP leadership picked Alan Keyes as Ryan's replacement in the race. He lost to Obama 27% to 70%.
Correction: Ryan ran for the US Senate seat, not the Illinois Senate.
Then, after Obozo won the primary by thus disposing of Hull and attacking him as a wife beater, Obozo drew an apparently fine young man named Jack Ryan as a GOP opponent. Ryan, as you note, had been married to and divorced from Jeri Ryan (Seven of Nine). Their divorce records had also been sealed. IIRC, the Chicago Tribune (former employer of Robert Axelrod) got a California court to unseal those records which included the claim that Jack Ryan wanted Jeri Ryan to join him in performing sexual acts in front of an audience at a private sex club for exhibitionists at Harrison, New York. Assuming that charge was in some sense true, she declined the offer if any. Her father publicly vouched for Jack Ryan's character in response to those charges but again to no avail.
Jack Ryan would have otherwise been a worthy successor to retiring Senator Peter Fitzgerald. Ryan spent a lot of HIS OWN money to win the primary. His self-made fortune was probably short of your claim (namely about $40 million IIRC). He had graduated Dartmouth and been quite successful in investment banking. He had then volunteered to teach ghetto students in the Chicago public school system so that the talented among them might learn from his successful career. He was turned down because he had not appeased the public edumakashun gods and the National Edumakashun Collective or Association by obtaining that ohhhhh soooooo necessary and useful degree in edumakshun. So he went to a Franciscan Catholic high school on the South Side of Chicago (the war zone) instead and, by all reports, did a fine job there at that largely African American school.
The foregoing which led to the election of Obozo to the Senate is "the Chicago Way" as practiced by Obozo, Axelrod, Jarrett and their, ummmm, comrades.
Ultimate GOP nominee Alan Keyes would certainly have been a far better senator than Obozo. But that's easy. Charles Manson might well have made a better senator than Obozo.
AND, of course, now that he is dead, Abraham Lincoln is probably a reliable Demonrat voter in Chicago. He is but a shade over 200 years old and Demonrat voting registrations are forever in Chicago. Whoever is too busy or dead to vote in person can be voted by the Machine. That Machine is very into servicing the graveyard vote.
Illinois: where our governors make our license plates with their very own hands!