Hindsight is $20/$20/$20

Those of us who have spent a day at the races are familiar with the two very distinct types of gambler's remorse.

The first type is reserved for a day spent betting to win on horses that finished up the track - or worse - standing along the fence at the end of the tenth race clutching a fistful of failed Pick 3 tickets - each one two/thirds "successful".

The second type of remorse belongs to those days where everything you touch turns to gold - but you wish it had turned to platinum. No matter how much money you wager on a 10-1 winner, you'll always wish you'd spent more. "Why," you'll argue with yourself, "Why did I not bet $20 to win instead of $10...."

Wednesday night at Woodbine I experienced the latter of these two evils. I went into the evening with a good tip from someone I'll call the Friendly Stranger...this is a friend who occasionally will email me with a blurb like, "Major Eddie G could likely route today on the front end" which is a strong indication to me that something positive is about to happen. The Friendly Stranger only calls with the good stuff. Despite not having even seen the Form yet, I immediately logged into my HPI account and advance wagered $10 win and show. The Major, at 9-1, led the whole way around the track only to be nipped at the wire by Highvale. The payoff? $8.30 to place, $6.00 to show.

"What about Win/Place" says the internal voice, "or why not across the board?"

Undaunted, I was happy with a small victory and was looking forward to wagering on a card, that due to a late dinner, I was only able to get tucked into from the fifth race onward. The key race this evening was the 7th race - The Victoriana Stakes, a six furlong sprint for two year old fillies, and it featured a favourite of mine - Cawaja Beach. Here's a horse I can key!

Immediately, I went to work on a mastermind Pick 3 ticket. Race five was a mess of ten maiden fillies with a lukewarm favourite. The sort of race that makes the "Bet All" button light up in gold - but I held back and sensibly threw out the favourite and then used four horses, including Keep Safe as it was being steered by Chantal Sutherland. Chantal rode brilliantly taking the maiden from ninth at the half to second by the top of the stretch and furiously scrubbed the rookie home at 8-1. Brilliant.

The sixth race is where I made my mistake. By this point, I had already wagered my Pick 3 and I was confident with leading rider Jim Mcaleney on the favourite (plus two other 'just in case' types.) So happy was I, that I didn't bother looking ahead to race eight following the sure thing that would be Cawaja Beach. Instead, I sat back and watched as Mcaleney surfed home on Foam to win by a length and a half. Two thirds of the way to my Pick 3 and the favourite in the final leg - not bad work, if I do say so myself.

It was at this point, that I looked at the eighth and final race on the card. This six furlong $12K claimer was stuffed to the brim with twelve horses that no one wanted to make the favourite. Exactly the sort of race that the "Bet All" button was invented for. Since I was so sure of my Pick 3, I wagered on a $1 late double of Cawaja Beach with ALL.

So, now we're at the Victoriana Stakes and I'm looking at Cawaja Beach and seeing dollar signs. Jockey Daniel David looks confident and I can't wait for the two-year olds to get in the gate and get going. Eurico Rosa Da Silva rushes Dash It Dreamer out of the gate and into a swift lead, pulling out a quarter in 22.16. In hot pursuit is Mcaleney on Stranger Things and Patrick Husbands on Minkredible. At the back of the pack, you'll find Daniel David choking Cawaja Beach with a very tight grip. At least you were able to find that until he disappeared from the screen entirely. This is not what you want to see in a six furlong sprint.

And around the track they go, a half in a swift 44.99 and still no sign of Cawaja Beach. With nothing to look at, my imagination wanders to David sitting on her back and doing his best to distract the filly from racing, "Hey Beach, did you see that colt in Barn 3 checking you out?" while friends of David sprint onto the track and set up fake construction detour signs in an elaborate attempt to ruin my potential $167 Pick 3.

But wait...as the horses hit the far turn, announcer Dan Loiselle's voice perked up and he bellowed that Cawaja Beach was on the move. Surely it's too late now. Fifth at the top of the stretch, David worked his way into the middle of the track and took dead aim at the leaders. One by one, they all fell down as the long striding filly gobbled up racetrack as she won her third stakes of the season by a length and a quarter. My fingerprints were embedded in my armrest. What a ride. After the race, a jovial David said, "I knew down the backstretch she was going to win..."

How? How could he possibly have known he could win a race where the other horses must have looked like ants they were so far in front of him.

The win put me in a favouite position of all punters - courtesy of the "Bet All" button, I was going to win the late double. It was just a matter of how much - and I was not surprised to watch a 10-1 shot chase down a 22-1 shot in the stretch to turn a potential $170 double into a $77 winning ticket. Not bad.

Some money made and a successful night of wagering concluded, but as I drifted off to sleep the remorse came drifting in, "If you were so sure of the eight race longshot, why didn't you Pick 3 from the sixth race as well?"

And that was only one scenario. Those of you that follow the game could probably drive holes through the flaws in my wagering, but the important part is I enjoyed the night and the thrill of a serious ride courtesy of Daniel David and Cawaja Beach.