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Picks, predictions for Rays vs. Cubs on Monday, May 29

Teddy Ricketson shares their top picks on DraftKings Sportsbook for Rays-Cubs on Monday, May 29th.

Marcus Stroman #0 of the Chicago Cubs pitches against the New York Mets at Wrigley Field on May 24, 2023 in Chicago, Illinois. Photo by Jamie Sabau/Getty Images

The Tampa Bay Rays (39-16) and the Chicago Cubs (22-30) will begin a three-game series on Monday, May 29. First pitch from Wrigley Field in Chicago, Illinois is set for 2:20 p.m. ET. Tampa Bay will send rookie Taj Bradley (3-1, 4.44 ERA) to the mound, while Chicago counters with its ace, Marcus Stroman (4-4, 2.95 ERA).

The Rays are the -125 road favorites at DraftKings Sportsbook. The Cubs are slight +105 underdogs, and the run total is set at eight.

Rays-Cubs picks: Monday, May 29

Injury report


Day-to-day: RP Pete Fairbanks (hip)

Out: RP Zack Littell (shoulder)


RP: Brad Boxberger (forearm), OF Cody Bellinger (knee)

Starting pitchers

Taj Bradley vs. Marcus Stroman

Bradley will be making his sixth start of the season. It was a brutal time out in his last appearance, as Tampa Bay took a 20-1 beating from the Toronto Blue Jays (although throwing a position player in the ninth had a lot to do with that). Bradley only lasted four innings and allowed four earned runs on nine hits. He did strike out seven without allowing a walk but took his first loss of the 2023 campaign.

This will be Stroman’s 12th start of the season, coming off consecutive wins. His last time out against the New York Mets was his best outing of the season, pitching eight innings and allowing two earned on just four hits. The righty struck out three and walked two to notch his fourth win of the year.

Over/Under pick

Each of these teams has seen ample runs scored in their recent games, with pitching staffs that are strugglingn right now. Stroman has been good this year but has still been known to give up runs, so he and Bradley should help the over hit on a warm day at Wrigley.

Pick: Over 8

Moneyline pick

Tampa Bay has gone 4-1 over its last five, while Chicago has gone 1-4 in that same span. The lone Cubs’ win was when Stroman was on the mound. Bradley has been shaky at best since being in the big leagues, and Stroman has been consistent all year. The question becomes which team has the better chance of providing the run support to their starter, and on Monday, that’s the Cubs.

Pick: Cubs