A group of 7 of us went in for Jeff Allen's picks in fall 1999 while I was in college. One of my buddies had gotten his GOY the week before without telling anyone (Oklahoma over Baylor) and that covered with room to spare, and since he unloaded on it and won, we all wanted in on this goldmine.
To be honest, the guy's picks were decent. Maryland +18.5 over Georgia Tech on a Thursday night was a 20* play, and to this day that remains the biggest bet I've ever made. I won by the hook (49-31 final), but GT shanked a field goal with like two minutes left that would've just killed me. Like Kosar, I did the charge-it-on-Mom's-CC thing, thinking it was free money and I was going to win and pay her off, no problem. Thankfully, I could since I won, but that missed FG did enough to scare me from ever betting that stupid again. If that FG had been good, I had no outs to pay her back if it lost.
But since I was the one who bought the picks, I got calls... and calls.... and calls. Thankfully, they always came up "unavailable" on caller ID so I was able to avoid them for the most part. But christ it was annoying. Finally I switched to a cell phone only, and haven't had to worry about them since.