How to Bet the Kentucky Derby With Friends

Photo by Penelope P. Miller/America's Best Racing
There are less than two weeks left until the first Saturday in May rolls around and the starting gates pop open for America’s greatest and most famous horse race. That means time is running out on fashioning a way to spend Kentucky Derby day chasing some gargantuan payoffs with your friends in a fun and interactive manner.
Adhering to the notion that there’s strength in numbers, Derby day at Churchill Downs traditionally offers a day-long slate of races that are the proper setting for groups of friends to pool their money and try to cash some lucrative exotic wagers.
The concept is actually pretty simple. You approach your friends about taking a small slice of their Derby day betting bankroll and putting it into a pot that will be wagered on behalf of the entire group with the winnings divided evenly.
With a betting syndicate like that, if you can get 10 people to ante up a modest $40 apiece, you would have $400 to put in play.
Of course, there’s more involved in this venture than collecting money.
As Captain Obvious will point out, you need to pick some winners. That goes without saying.
But equally important is the strategy involved in making the wagers.
That starts with your mindset. Some betting syndicates funded by professional gamblers can total tens of thousands of dollars.
But if you’re more of a beginner or weekend player, you’ll need a far more conservative approach.
Let’s say, you have a bankroll of $200 for Derby day. If you join that 10-person syndicate, it will leave you with $160 and, if constructed properly, that $40 will give a ton of action with bets that might be out of your pay grade if you were betting on your own.
For those folks with limited financial resources, the syndicate should be constructed to complement their own wagering. They should use it to chase Pick 3 or Pick 4s, or triples or superfectas that they could not do on their own.
For example, from that $400, why should anyone bet $10 to win on Nyquist? That’s the type of bet that can be easily covered by some of the remaining $160 in everybody’s original bankroll. Ditto for doubles and exactas.
Instead, how would you like to be alive to 10 horses in the Kentucky Derby with a Pick 3 ticket? It’s not as far-fetched as it might seem, thanks to a syndicate.
With that pool of cash, a $2 Pick 3 with three horses in the first leg, three in the second leg and then 10 in the Kentucky Derby could be purchased for $180 (the math is 3 x 3 x 10 which equals 90 combinations at $2 apiece for $180).
How about boxing seven Derby horses in the trifecta? That bet would cost you $210.  
Either one of those bets could easily return $2,000 or $3,000, and with a $200 bankroll, you would probably hesitate to make either wager.
Yet by pooling money, you could have a piece of both tickets and still have that $160 to invest in win tickets or exotic wagers with far less combinations, such as exactas and doubles.
It’s the best of both worlds. You’ll have more wagering dollars and more fun by sharing it with friends who for years to come will no doubt remind you of the big score you notched together or the loss by a nose that cost you a couple thousand bucks – and maybe even send you a meme about it.   
And all it takes is a few phone calls or texts to line up your friends and someone to coordinate the wagering strategy and pick out the best races to play, and you’re on your way.
So don’t wait too much longer. Starting dialing those contacts on your cell phone.
When it comes to wagering on Kentucky Derby day, it’s the more, the better.