Washington (CNN) - He's one of Chicago's most beloved citizens, a former star player who later led the NFL Bears to a Super Bowl title as coach.
But Mike Ditka's biggest regret? Losing a 1986 playoff game that could have propelled the “Monsters of the Midway” to back-to-back championships. No.
It was his decision to not throw his hat into the 2004 U.S. Senate race and challenge a then little-known state senator, Barack Obama.
Speaking to a crowd of 100 in Watford, North Dakota, earlier this month, “da coach” expressed his regret over his political non-campaign.
"Biggest mistake I've ever made," Ditka said of the decision. "Not that I would have won, but I probably would have and he wouldn’t be in the White House."
After GOP front runner Jack Ryan withdrew from the contest, prominent state and national Republicans, including then-House Speaker Dennis Hastert, then-House Majority Leader Tom DeLay, and former Sen. George Allen, tried to recruit "Iron Mike" to run for the open seat.
Ditka declined, citing obligations to his chain of steakhouses and duties at ESPN.
"Five [or] six years ago, I would have jumped on it," Ditka told CNN in 2004 after announcing he would not enter the race. "I would have ran with it and I know this - that I would make a good senator because I'm for the people."