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Best Max Fried prop bet for Red Sox vs. Yankees on Tuesday 9/30/25

Best Max Fried prop bet for Red Sox vs. Yankees on Tuesday 9/30/25

Published:

By: Bryan Armetta

There’s nothing quite as exciting as a Yankees-Red Sox postseason duel. These two rivals will take the field for the start of a three-game do-or-die set on Tuesday.

Boston will send Cy Young candidate Garrett Crochet to the mound. That ramps up the pressure on New York’s Max Fried. Can the Yankees’ ace toss a gem against the Red Sox?

New York is favored (-137) over Boston, with the over/under set at seven runs. Before the start of Tuesday’s postseason matchup, here’s my favorite Max Fried player prop bet on DraftKings Sportsbook.


Max Fried over 5.5 strikeouts (-147)

Most of the conversation entering this contest is how New York’s bats will attack Crochet. However, he isn’t the only star pitcher taking the hill tonight. Fried was the American League Pitcher of the Month in September. During five starts, he notched a 1.89 ERA, 1.05 WHIP and 35 strikeouts. That includes a 5.1-inning, two-run showing vs. the Red Sox at Fenway Park.

Fried, during his debut season in the Bronx, has done well against the team’s arch-rivals. Through three starts against Boston, he’s allowed just four earned runs (1.96 ERA). Most impressive is that two of those appearances came at Fenway, a notoriously difficult place for left-handers to pitch. Tonight’s matchup, at Yankee Stadium, provides more room in the outfield.

This Red Sox lineup, while dangerous, is missing rookie standout Roman Anthony. That takes away a bat that could have given Fried some trouble at the top of the order. On the road, Boston has recorded 227 total strikeouts against left-handed pitching. That’s the third-highest mark in baseball this season.

Seven different Red Sox hitters have struck out at least three times in their career against Fried. While that doesn’t mean history is doomed to repeat itself, it’s not a great sign. In addition, the 31-year-old has produced at least six K’s in each of his previous three meetings with Boston. The veteran reached that threshold in seven of his last ten appearances.

Even at less than 100%, this Red Sox lineup is capable of doing damage. Still, it’s difficult to bet against New York’s All-Star given the way he’s been pitching. On a night where the Yankees need a solid performance from Fried, expect the southpaw to deliver.

Bryan Armetta is a New York-based writer that has spent over eight years in sports media. Working for DraftKings since 2024, he currently serves as a writer, editor and analyst for all things sports and pop culture. Bryan specializes in MLB, NBA, NFL, college sports and entertainment content. Prior to his time at DKN, he worked for MLB Network, NHL Network and SiriusXM Sports.
Disclaimer

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.