Former Chicago Bears legend and coach Mike Ditka said the biggest mistake he has ever made was not challenging then-state Senator Barack Obama for Illinois's U.S. Senate seat in 2004, saying he "probably" would have beaten Obama and prevented him from winning the White House.
“Biggest mistake I’ve ever made,” Ditka recently said at an event in North Dakota, according to the Dickinson Press. “Not that I would have won, but I probably would have and he wouldn’t be in the White House.”
Ditka decided against seeking the Republican Senate nomination in 2004 in Illinois. Obama's path to his party's nomination was made easier when details about Democrat Blair Hull's divorce came to light. Hull was a Senate candidate for whom David Axelrod had wanted to work before he signed on to Obama's campaign.
Then, details about the sex clubs that Jack Ryan, the Republican candidate, visited with his former wife Jeri were released from divorce files and sensationalized, forcing Ryan to withdraw from the race. That left Republicans with a barren field of candidates. Eventually, Obama ran against Alan Keyes, an out-of-state candidate whom Illinois Republicans chose to run against Obama. Obama clobbered Keyes in the general election by getting 70% of the vote en route to the Senate and ultimately the White House.