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Handicapper John Hyslop is here with his best bets and longshot picks for the 2022 Kentucky Derby.

Kentucky Derby Longshot Picks: Back This Expert's 20/1 Derby Picks

The thing I look forward to the most on Kentucky Derby Saturday is the extra gambling. The nice little three-minute sweat at 6:57 pm ET (it never starts on time) is pure gold. If I was in charge there would be a "big" horse race every Saturday at 6:57 pm ET (it would start on time every week). Gambling is the cornerstone of any great weekend. Everyone knows that. So having a "big" horse race every Saturday just makes sense. We're not reinventing the wheel here. Obviously, we need to bet this race today and I'm not just talking about a Derby Pool. My wife, kids, and I throw $5 (I pay for everyone so it's a shit bet for me) into a pot and draw numbers out of a hat which is fine but I'm talking about real bets here. Lucky for us, I've read everything there is to read about these animals and in doing so I may have figured out horse racing. We should bet this race.

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Kentucky Derby Long Shot Picks

#5 Smile Happy 20/1 (Bet $100 to Win $2000)

#16 CyberKnife 20/1 (Bet $100 to Win $2000)

People are saying this race is deep so what that means is you have to bet a couple of long shots. When going with long shots, I like sentimental horses. Call me soft, but we're talking about animals running in a circle here. Anything can happen.

First one is Smile Happy. This one comes from the Macklin Family who from all accounts are awesome people. The family has been in the horse business for 31 years and now are finally at the Kentucky Derby. The thing is, the horse is fast. It legit almost beat the favorite, Zandon, in its last race. Some people are saying it pretty much did beat Zandon (other than finishing behind him). After reading about the Macklin Family, in my opinion, this is our best shot at betting on a Disney movie. If this horse wins, they're making a movie and every time we see it we can be like, "I had that horse that day". Feels right.

The other one that jumps off the page is CyberKnife. This one is crazy because he's named after a life-saving cancer treatment. The treatment so far has saved 1152 people since CyberKnife was born. The treatment is fast too (just like the horse). People spend five or six days being treated this way instead of the alternative which can be six to eight weeks. I feel like we're going to be hearing about it on the telecast so we should get out ahead of this by betting the horse.

Obviously, you don't want to show up to your derby party with only two long shots because there's always some loudmouth there with only favorites in his pocket. The best defense for this guy is by tossing out a couple win bets on #10 Zander and #3 EpiCenter. I like to wait until closer to post before betting on the absolute favorites but you can do you. Everyone knows losses don't count on Saturdays so you can go crazy here if you want. It's fine.

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Article Author


John has spent the past 20+ years betting sports on a daily basis and is considered by many to be a walking sports betting encyclopedia. From obscure player props to sides and totals, if there is an angle, John will find it. His work has appeared on Rotogrinders and he has been a regular on sports talk radio stations across the country. Based in the US, John operates a blog & podcast, Sports Bets Beers, which covers betting angles in the NFL, NBA, MLB, & NHL.


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