Doug Gottlieb is in town MC'n the College basketball hall of fame induction tonight. My friend meets him at the pre party and starts talking with him, eventually as doug is getting ready to go to the main event my friend makes a quip about Gottliebs inability to make free throws.
Gottlieb says "All right lets go, how much do you have on you".
Turns out my friend has a large amount of cash on him since he planned to play poker after the event. They play best out of 10 free throws in the indoor basketball arena area. Doug jumped out to an early lead then bricked the last 4 and my friend ended up beating him by 1.
Gottlieb had to run off to MC the main event but promised to "settle up" before the night was over. There is apparently video of the contest.