Was in an airport with a lefty associate watching CNN announce jury selection had been completed for the OJ trial. Upon hearing the makeup of the jury, I said to my companion OJ wouldn't be convicted. It'd be either an acquittal or a hung jury. He thought that was absurd and went on a rant about how juries generally come to the right decisions, yada, yada, yada. I replied at least one black juror would never vote guilty for OJ, period.
He then wanted to make a bet on it so I said OK, ten bucks. He shot back with make it a hundred, to which I agreed. We spoke a bunch of times during the trial, during which I often reminded him of our wager. He never paid up. When I left that company about a year later I left a note with his secretary reminding him and included my new snail mail address, which I figured he'd ignore but wanted to remind him he'd reneged and his credibility was thus in the dumper.
A few years after that I ran into him at an industry convention, said hello, and asked him how'd that OJ trial go? If I could have gotten a picture of the nasty look on his face at that moment it would have been worth the hundred I never got.