The crown jewel of Breeders’ Cup betting is the Pick Six. If you hit a Breeders’ Cup Pick Six just once in your betting career, you have a story that you can tell for the rest of your life. To win the bet you have to have the right combination of bankroll, skill and luck — and people who know the sport respect the bet. If you are drawn to the Pick Six but don’t have a whole lot of experience with it then here are five factors to keep in mind:

Realize how hard this is

If you bet on the Pick Six, you are more than likely going to lose. That’s just the reality of it. Picking the winner of one Breeders’ Cup race is tough enough. Doing it six races in a row is much, much harder than it sounds. Proof? In 2005, and again in 2006, there was not a single ticket sold that had all six winners correct. In 1999, 2003 and 2009 there was just one winner. Each year, thousands of bettors invest millions of dollars in the Pick Six, and most wind up poorer and more frustrated than when they began. The chances of winning are a little better than winning the lottery, but you’ll spend a whole lot more on tickets. That doesn’t mean you shouldn’t play the Pick Six, of course — it’s one of the most fun and most challenging options in all of sports betting. If you are looking at it as an easy path to riches, though, you are barking up the wrong tree.

Question whether it is the right bet for you

Once you have a sense of how tough this bet is to win, you need to ask if it is what makes sense for you. The biggest factor is whether you can afford it. You might as well just play the lottery if you are only going to buy a combination or two in the Pick Six. To properly give yourself a chance of success, you need to buy dozens or even hundreds of combinations, and at $2 per combination that can put a big dent in your wallet. You also need to be able to handicap well — or have access to someone who can. If you can’t separate the contenders from the pretenders, you are making it too hard on yourself. You also need to be sure that the Pick Six is the best place for you to balance a potential payoff with the risk involved. The Pick Four doesn’t pay nearly as much, but it can also be played effectively with a much smaller investment, so the risk and potential return on investment could be more attractive. I personally really like the Pick Three on Breeders’ Cup day — the cost is manageable, there is a new opportunity to bet with each race, and if you hit a decent priced horse or two, the payoff can be very attractive.

There is strength in numbers

Sharing a small piece of the jackpot is far more attractive than having a full share of a losing ticket. Oftentimes the best way to attack the Pick Six is to pool your money with some other bettors. That allows you to cover more combinations, go deeper in challenging races, and improve your chances of success. You can make smaller returns for having most of the winners correct, so having more tickets gives you a better chance of breaking even or making a small profit even if you don’t hit the jackpot.

Find a single

To create a ticket that is affordable but still gives you a good chance to win, you almost certainly need to find a single — one horse in one race that you are so confident in that you aren’t going to bet on any others in that race. That will make you nervous about that race, but it will lower the cost of the ticket significantly, and will allow you to go deeper in other races.

Make multiple tickets

As much as handicapping, the key to success in the Pick Six is structuring your bets effectively. Instead of one big ticket in which you pick five or six horses in each race, you need to create multiple smaller tickets. One ticket might have your top choices in four races along with live longshots in the other two, while another could have three top-level contenders and three second-choice runners. By structuring your bets this way you are able to cover your most likely — and therefore most potentially profitable — bets while costing much less.

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Read more articles by Trevor Whenham