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Best Red Sox Futures Bets 2023: Chris Sale, Cy Young Winner?

Hear me out.

Detroit Tigers v Boston Red Sox Photo by Maddie Malhotra/Boston Red Sox/Getty Images

With online sports gambling now legal in Massachusetts, we at Over the Monster would like to obtain sportsbook sponsorships. To that end, this is a new regular column about betting on the Red Sox.

Welcome to the Over the Monster gambling column. The good news: We’re all still alive. The bad news: I’m not a gambler, in the truest sense of the word. Yes, I make bets, irregularly and not for a lot of money, but I don’t live the life. I’m not one of Those Guys. I am merely pretending to be.

You have been warned.

No beating around the bush, the best Red Sox-related bet of the season is for the team to win more than 78.5 games, which it absolutely will do, hence it’s a good bet. They sucked balls last year compared to expectations yet still won 78 games, and while they lost some guys they added guys too and they probably won’t, like, give up this year. On top of that, the more balanced schedule means they’re playing more outside the AL East bloodsport division and, even within the division, are the Orioles gonna Do It (finish above last place) again? I doubt it. This line is at their floor. Grab it while you can.

If you’re looking for something riskier with a better payout, I’d take Chris Sale +8000 to win the AL Cy Young Award. Obviously it’s unlikely, but I don’t think it’s as unlikely as the odds suggest and worst case scenario you have a really fun April imagining winning on an 80-1 payout.

Sale (+8000) is nowhere near the head of the pack. Jacob deGrom is the favorite at +500, which is insanity given his injury history (he’s the inverse of Sale, in a way, in that his injuries are being undercounted here) with Gerrit Cole, Dylan Cease and Alek Manoah, a personal favorite, right behind. For context Sale’s odds are identical or similar to Sonny Gray’s, Chris Bassitt’s and Lance Lynn’s, among others.

These are good pitchers who, in order to win the Cy Young Award, would have to pitch at maximum skill over an entire season and hope the rest of the field disappoints. It’s Rick Porcello Cy Young Award territory, by definition.

Sale does not belong in this group. If Sale completes a full season without getting hurt he would be lightyears beyond these guys even pitching at a B+ level, which is as bad as he gets.

To be clear: I do not think it will happen. But at 80-1 odds it’s worth a couple bucks because there are so few players in baseball history, comparatively speaking, who are just better than everyone else. Sale is one of them, and if this is really the end, you’ll have to eat your cash. Sorry about that. I’m just sayin’.