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MLB Best Bets: Top Starting Pitcher Prop Bets for Monday, 7/27/26

MLB Best Bets: Top Starting Pitcher Prop Bets for Monday, 7/27/26

Published:

By: Cooper Albers

We’ve got 12 games on the board for Monday’s MLB slate, bringing a loaded batch of prop bets with 24 starting pitchers to choose from.

Let’s dive into a few of my favorites on DraftKings Sportsbook.


Best MLB player prop bets on DraftKings Sportsbook

Keider Montero 5+ Strikeouts (-118)

Detroit is home to one of baseball’s most formidable pitching staffs, with Keider Montero playing an essential role. The young right-hander, 26, has posted a career-best 3.14 ERA (3.38 xERA) across 22 games (16 starts) for the Tigers, ranking fifth in MLB with a 0.96 WHIP across 106 innings. 

Montero enters Monday’s series opener against the Orioles at Comerica Park with a 1.96 ERA over 18.1 frames since the beginning of July. In his last outing, Montero held the surging Cubs’ lineup to one earned run over 5.1 innings while piling up eight strikeouts. It was his third straight appearance with five or more K’s. He’s well-positioned to follow suit against Baltimore, which is liable for MLB’s fourth-highest strikeout rate in 2026 (24.3 percent).


Chase Burns Over 16.5 Outs (-121)

Cincinnati’s Chase Burns has been the epitome of consistency in his sophomore campaign. Holding a remarkable 12–1 record, the right-handed fireballer ranks fourth in MLB with a 2.42 ERA (3.14 xERA) across 19 starts (107.2 IP) for the Reds in 2026. He’s recorded at least 15 outs (5.0 IP) in every single appearance, including 11 performances with 17 or more. 

Monday shouldn’t be much different. Burns, 23, has drawn a favorable matchup with a lifeless Cleveland lineup that ranks 25th in wRC+ and 29th in wOBA and xwOBA in 2026. The Guardians have dropped five straight games — getting shut out in back-to-back contests heading into the series opener at Great American Ball Park.


Max Fried Over 14.5 Outs (-142)

Max Fried didn’t skip a beat in his first start back from the injured list. Facing the Pirates on July 22, the star southpaw, 32, restricted the potent Pirates’ lineup to one hit over five innings while racking up seven strikeouts. Fried enters Monday’s series opener at Rate Field with a 2.97 ERA and an even better 2.48 xERA across 11 starts (66.2 IP) for the Yankees in 2026. Excluding his premature exit due to injury on May 13, the World Series champ has collected at least 15 outs (5.0 IP) in every single start.  

And there couldn’t be a better time to face the White Sox. While the club — currently staked to a 2.5-game lead over the American League Central — has made for one of the league’s most compelling comeback stories, its offense has ground to a screeching halt over the past month. Since the beginning of July, Chicago ranks 27th in wRC+, 26th in wOBA, and 22nd in xwOBA.

I am a promoter at DraftKings and am also an avid fan and user and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.