Red Sox vs Yankees Prop Picks: AL Wild Card Series Game 2

Dustin Saracini -  - Betting Analyst at Covers.com
Dustin Saracini • Betting Analyst 14+ years betting experience
Updated: Sep 30, 2026 , 02:21 PM ET • 4 min read

Fried's victims tonight include Trevor Story (39% K rate), Ceddanne Rafaela (33%), and Jarren Duran (37%) — they'll all be in tough shape come Game 2. Back his strikeout number with me.

Photo By - Reuters Connect - New York Yankees pitcher Max Fried (54) pitches during the first inning at Yankee Stadium.

Boston has its back against the wall in Game 2 of the AL Wild Card series, and I'm expecting a pitcher's duel in my Red Sox vs. Yankees prop picks.

The first pitch between Boston Red Sox ace Sonny Gray and Max Fried flies tonight at 8 p.m. ET from Yankee Stadium, with a trip to the ALDS on the line for the New York Yankees. The Tampa Bay Rays are waiting patiently.

Tap into all of my MLB picks — as well as Chris Hatfield's Red Sox vs. Yankees predictions — for today's slate, and let's keep building our bankroll on Wednesday, Sept. 30.

Best Red Sox vs Yankees props

For help understanding probabilities, see our odds calculator.

Pick Probability
 Yankees Max Fried Over 5.5 strikeouts 47%
 Red Sox Sonny Gray Over 5.5 strikeouts 46%
 Yankees Ben Rice 2+ total bases 42%
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Prop pick #1: Max Fried Over 5.5 strikeouts

The playoffs haven't necessarily been kind to Max Fried, who got lit up by the Blue Jays the last time he touched a postseason mound. However, with a deep-rooted rivalry opposite the Boston Red Sox, I expect Fried to bounce back against a team he's striking out at a 26% clip across 145 plate appearances. 

Who am I looking at to be the victims tonight? Trevor Story (39% K rate), Ceddanne Rafaela (33%), and Jarren Duran (37%) will all be in tough shape come Game 2.

Prop pick #2: Sonny Gray Over 5.5 strikeouts

Yes, we're looking at a pitcher's duel with Sonny Gray on the mound for the visitors, and he's striking the New York Yankees out at a 24% clip (26% whiff rate) over 161 career at-bats against him in this matchup. 

After Game 1, the Boston bullpen is fully exposed, so don't be surprised if he gets left in with the season on the line. Working with that much volume, Gray should reach six strikeouts tonight.


More MLB playoff predictions today


Prop pick #3: Ben Rice 2+ total bases

Ben Rice is undoubtedly the hottest hitter in this Yankees lineup and has a strong history against Gray. Even though it's a smaller sample size, it's something to draw from, as Rice is 3-for-7 with two homers (.810 xSLG) against the Red Sox righty.

With a 4-for-5 night (including a grand slam) under his belt in Game 1, expect Rice to do more damage if Boston actually pitches to him.

Dustin Saracini's 2026 Transparency Record
  • Prop picks: 1-2, -0.82 units
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Dustin Saracini
Betting Analyst

Dustin Saracini is a betting analyst at Covers with over 14 years of experience in the sports betting industry. Throughout his career, Dustin has hosted multiple betting shows- breaking down NBA, NFL, PGA, and MLB markets alongside top handicappers - and has appeared as a Super Bowl consultant for CNN. A disciplined daily bettor who extensively line-shops across FanDuel, DraftKings, BetMGM, and Caesars, his sharpest edges lie in MLB and the NFL (followed closely by the NHL and NBA). A self-proclaimed NRFI guru targeting his second straight +10u MLB season, Dustin holds a Broadcast Journalism degree from Western University (2014). For daily picks, market strategies, and insights, follow him on X (Twitter) @DustinSaracini.

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