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MLB Best Bets: Will any pitcher win 20 games?

By Jared Shlensky | Last updated 3/15/23

Caesars Sportsbook has a myriad of MLB prop bets and future bets still available to wager on with the regular season still two weeks away, but some of the lower-risk prop bets are in the "regular-season specials" section. If you haven't checked it out yet, you need to, but for the time being, we'll briefly fill you in.

Just like the majority of the sportsbooks — FanDuel, DraftKings, PointsBet, Barstool, BetMGM, etc. — Caesars allows you to bet on who is going to win the World Series, win a particular division or make the playoffs but unlike most of the books, Caesars has some real specific types of bets too. Like whether or not any team will win 100 or more games or if any player will record 200 or more hits and so on.

But the one prop bet in the "regular-season specials" tab that caught our eye was whether or not any pitcher will win at least 20 games. The line is currently -115 for both "yes" and "no" on whether or not any pitcher will win 20 or more games, and we're surprised.

It's quite rare the lead league winner in wins doesn't get to 20, and that's why we think you should bet "yes" immediately on this prop bet special. The line could shift to -125 yes/-105 no before you know it, so get this bet in now.

Last year Kyle Wright was the only pitcher to win 20 or more games with 21, and we're surprised he was the only pitcher to record 20 wins, especially when you do the math and see 31 different pitchers made at least 31 starts. But to our point, one pitcher did reach the 20-win plateau.

We're definitely seeing fewer and fewer 20-game winners, but it is still happening year in and year out. In fact, there's been at least one 20-game winner each of the last four seasons and 10 of the last 12. Some guys have incentive bonuses in their contracts based on how many games they win and how many starts they make, so as long as a dozen or so pitchers are making 31+ plus starts each season, we'll always bet there'll be at least one 20-game winner per season.

The Bet: Pitcher to win 20 or more regular-season games (Yes, -115 odds)

Bet $115 to win $100

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