Walk-Off Wagers: MLB Best Bets Today (Bet on Pirates to Upset Cubs, Clarke Schmidt on Thursday)

BetSided's Peter Dewey breaks down his favorite plays in Major League Baseball on May 16.
Pittsburgh Pirates starting pitcher Jared Jones (37).
Pittsburgh Pirates starting pitcher Jared Jones (37). / David Dermer-USA TODAY Sports
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It’s a travel day in Major League Baseball, which means there are way fewer games to pick from on Thursday.

The New York Yankees and Minnesota Twins get the action started at 1:10 p.m. EST, and there is one starter in that game that I think could turn in a strong performance. 

Not only that, but today’s MLB Best Bets feature an upset pick in an NL Central clash and a prop for one of the best starting pitchers in baseball so far in 2024. 

Let’s break down these picks and look to pay off this six-game slate with a few winners!

MLB Best Bets Today for May 16

Odds via DraftKings Sportsbook.

  • Clarke Schmidt UNDER 2.5 Earned Runs Allowed (-140)
  • Pittsburgh Pirates Moneyline (+110) vs. Chicago Cubs
  • Tyler Glasnow OVER 8.5 Strikeouts (-110)

Clarke Schmidt UNDER 2.5 Earned Runs Allowed (-140)

Yankees starter Clarke Schmidt has been one of the most consistent pitchers the team has over the last two seasons, but especially in 2024.

So far this season, Schmidt has not allowed more than three earned runs in any of his eight starts, and the Yankees are an impressive 7-1 straight up when he takes the mound.

Six of the eight outings for Schmidt this season have resulted in him allowing two or fewer earned runs, and he’s coming off his best game of the season – 6.2 scoreless innings in a win over the Tampa Bay Rays. 

Schmidt’s 2.95 ERA is backed up by a 3.77 Fielding Independent Pitching, and I think he’s in line to shut down the Twins on Thursday.

Pittsburgh Pirates Moneyline (+110) vs. Chicago Cubs

Rookie Jared Jones and the Pittsburgh Pirates are slight underdogs on the road on Thursday against All-Star Justin Steele and the Chicago Cubs.

Steele, who has made just three starts in 2024 due to injury, was rocked in his last outing, giving up six runs across four innings to this Pirates team. So, why are the Pirates dogs in this matchup?

Outside of the Cubbies being at home, I don’t really see the appeal for a bet on them here, especially since Steele hasn’t pitched deep into games, failing to get through five innings an all of his starts.

Chicago’s bullpen is beatable, posting a 4.47 ERA on the season, and the Cubs are 0-3 when Steele is on the bump in 2024. 

Jones, on the other hand, has been one of the better pitchers in the NL, posting a 2.68 ERA across eight outings. He’s allowed three or fewer earned runs in all eight of those starts.

That consistency is huge, and I think it’s the difference for the Pirates tonight. I can’t trust Steele – or this Cubs bullpen – until we see them perform better. 

Tyler Glasnow OVER 8.5 Strikeouts (-110)

Los Angeles Dodgers starter Tyler Glasnow has been lights out this season, posting a 2.53 ERA while striking out 73 batters in 57.0 innings of work across nine starts.

In his last six outings, Glasnow has recorded 14, five, 10, nine, 10 and 10 strikeouts, clearing this prop five times.

He’s in a prime spot to do it again on Thursday, as the Cincinnati Reds ranks sixth in Major League Baseball when it comes to the most strikeouts this season. The other thing working in Glasnow’s favor is that he’s pitched seven or more innings in four of his last six starts, giving him plenty of outs to rack up the K’s. 

This prop may seem high, but the Dodgers’ ace is more than capable of clearing it on Thursday.


Game odds refresh periodically and are subject to change.

Find Peter Dewey's betting record here You can also follow my daily plays on BetStamp here.