What’s the most money you’ve ever won or lost...

kevcat

Heisman
Feb 26, 2007
27,686
32,624
0
Kev what about you? Those super high 5’s and exotic bets are exciting when you hit and waiting on the payouts. That my friend is a addictive Drug!!!
My biggest payday was a pick 6 betting Belmont in 2009.

3 buddies and I decided to invest $250 a piece and try to hit it. The pool had grown to over $2 million after carrying over a couple of days.

We caught a couple of prices in the first four legs but only used 2 horses in the fifth leg and had a single in the final leg. We got a 7-2 shot home and then desperately needed the big favorite to win.

Well, it wasn’t easy, but the favorite got his head down at the wire and we knew we had a payday coming.

We ended splitting $360,000 four ways. We partied really hard that night.

These days I love the pick fives and pick fours. I’ve hit numerous pick fives that have paid anywhere from $60 to $54,000.

The pick fours really don’t pay as much as they once did since the pick 5 become commonplace a few years ago.
 
  • Like
Reactions: ThePunk

kevcat

Heisman
Feb 26, 2007
27,686
32,624
0
Kev what about you? Those super high 5’s and exotic bets are exciting when you hit and waiting on the payouts. That my friend is a addictive Drug!!!
It’s a crazy high for sure. I bet the early pick 5 at Belmont a week ago Thursday. I had gotten the first four legs, including beating the 1-5 favorite with. 35-1 shot in race 2.

I singled an obvious favorite in the last leg and he won easily. As the payouts scrolled on the bottom of TVG’s screen, I was hoping for at least $12,000. As it turned out, it paid just ovEr $10,000. Still fun.
 
Last edited:

kevcat

Heisman
Feb 26, 2007
27,686
32,624
0
Get the TwinSpires app and give us some daily picks. Lol damn 360,000

Well, I’ve also had some really expensive days. Lol.

I don’t do drugs. I like to drink, but betting the ponies gives me a high like I suppose meth or cocaine does to people.

As for the most I’ve lost in a day? About $18,000
 
Last edited:

ukalum1988

Heisman
Dec 21, 2014
11,883
30,418
113
....in a day betting sports? (Horse Racing included)

As a side, what were your lucky wins and tough beats?
I won $800 in a split-the-pot drawing at a HS football game 10yrs ago.

In actual gambling I won $157 on a trifecta at the Red Mile back in 1990. That was maybe the fifth or sixth race. Cashed my ticket and called it a day.

I only gamble occasionally, and I have a hard limit of stopping after I’ve lost ~ $100, which I’ve done numerous times.
 
  • Like
Reactions: kevcat

vhcat70

Heisman
Feb 5, 2003
57,418
38,482
0
Won $2K in a raffle. Most I lost in poker was $300-400. Counting the stock market, maybe $55K in a day.
 
  • Like
Reactions: kevcat

uksam21

All-American
Jan 14, 2013
3,932
5,058
0
$2000 on Kentucky cashball in 2014. I had a quick pick and my cashball was 24.

What's interesting about it was if I had gone with 21 which is my lucky number as cashball I would have hit the 200 K jackpot.
 
  • Like
Reactions: kevcat

bcw1029

All-Conference
Feb 24, 2007
1,506
2,482
0
$6200 on a Pick 4 back during the 2011 KY Derby, when Animal Kingdom won the Derby at 16-1. Paid for my European cruise to the Adriatic among other things.....

$96 bet
 
  • Like
Reactions: kevcat

BoulderCat_rivals187983

All-Conference
May 22, 2002
7,871
3,227
0
A rather meager $840. As a rule I rarely gamble with money. I won it in the office pool for the 1998 NCAA tournament. “Bet” you can guess who I picked to win it all.