Best MLB Bets Today: Fading Flaherty as he Continues to Flounder

Jack Flaherty was one of the best stories of the 2024 season, but his career turnaround was only temporary. The Tigers’ starter has just one quality start in 2025, and we don’t see that changing tonight. We’ll share why we are fading Flaherty below and two other bets we’ll be locking in. 

The odds we use are taken from Caesars Sportsbook. If you’d like to give Caesars a try, use promo code WSNDYW to claim a “Bet $1, Get Ten 100% Profit Boost Tokens” offer.

Minnesota Twins vs. Milwaukee Brewers (8:10 PM EST)

PICK: Twins ML (-115) at Caesars Sportsbook

Twins starter Joe Ryan (3-2, 2.74 ERA, 0.83 WHIP) has been nearly unhittable over his last three starts. He is 2-0 with a 0.95 ERA and 0.63 WHIP during that span, and that momentum will carry into tonight in Milwaukee.

The Brewers' lineup continues to hold them back in 2025. They have the sixth-lowest OPS (.665), and own a .209 average over the last week. They were shut out twice in their last series, and there is a great chance for that to happen again tonight.

Milwaukee will have Chad Patrick (2-3, 3.19 ERA, 1.25 WHIP) starting opposite Ryan tonight. The 26-year-old seemed like he was set to break out in 2025 after posting a 1.82 ERA in April, but the wheels have come off in May. We expect to see his struggles continue against the Twins team, which has been improving at the plate this month.

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Cleveland Guardians vs. Cincinnati Reds (6:40 PM EST)

PICK: Guardians ML (-125) at Caesars Sportsbook

Cleveland starter Tanner Bibee (3-3, 3.80 ERA, 1.22 WHIP) has been one of the top pitchers in the AL over the last month. He has a 2.16 ERA and 1.00 WHIP in his previous four starts, and will have an excellent opportunity to keep that hot streak going tonight.

The Reds have lost nine of their last 12 games, which includes a series loss to the lowly White Sox at home earlier this week. A big reason for their struggles has been the lineup, featuring five starters batting below the Mendoza Line (.200) over the last week. That includes Elly De La Cruz, who has a brutal .596 OPS in May.

Cincinnati will have Brady Singer (4-2, 4.97 ERA, 1.32 WHIP) on the mound to start tonight’s game. The 28-year-old started the season 4-0 with a 3.24 ERA, but has been hammered hard over his last two starts. He allowed 11 runs over a combined 8 ⅓ innings (11.88 ERA) in starts against the Astros and Braves. The Guardians' lineup isn’t overly intimidating, but they have been at least as good as those two teams.

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Detroit Tigers vs. Toronto Blue Jays (7:07 PM EST)

PICK: Blue Jays ML (-140) at Caesars Sportsbook

We are fading Jack Flaherty (1-5, 4.61 ERA, 1.24 WHIP) hard tonight. The 29-year-old has lost the edge that helped him deliver a surprising comeback campaign in 2024. We saw the issues start to pop up towards the end of last season, getting hit hard over he final three starts before posting a 7.36 playoff ERA. 

The righty has delivered just one quality start this season, and is 0-2 with a 9.35 ERA over his first two starts this month. He has remained confident when discussing his struggles, but we think his short time as an ace has ended.

The Jays' lineup is going to hit Falherty hard tonight. The lineup has gotten hot, posting a .309 average and .512 slugging percentage over the last week. Toronto’s offensive resurgence has helped the team win five of its previous seven games.

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