The first thing that came to mind for me was a horse called Chico Bambino in the 8th race, a $6,250 claimer, at now-defunct Playfair Race Course in Spokane, WA on October 12, 1986. I was 14 years old and my dad took me to the track every Sunday. He is just a casual fan and strictly a $2 bettor, but we always had a good time. We would read the form and I would make my pick, and he would bet it (with my money) and then he would bet whichever horse he chose.
So we were there and we were handicapping this race, and this horse had just won 10 days ago as the favorite by 5 lengths, and now he was on the board at 20-1! So I gave him my $2 and he bet his, and he came back to the rail with a $4 win ticket on this horse, who was usually a speed horse, but on this day he broke slow, but somehow managed to storm down the stretch to get up by a length, and paid $47 for a $2 win ticket. It was a great thrill to go back and have him collect $94.00 and then split it up between us. Even though it was the last race "Chico" ever won (he lost his last 28 starts) it still gave us a great memory.
Itsallgreektome was memorable for me too as I bet on him when he won his debut at Del Mar in 1989 at 27-1. There was about a 15-minute inquiry as he and another horse squeezed the favorite in tight quarters in the stretch, but after watching the board blink for what seemed like forever, Trevor came on and announced "No Change!" I quickly cashed my ticket before they changed their mind.
