How lucky are we? Meaningful, late-August baseball in the AL East pennant race is the marquee theater of this weekend, as Carlos Rodon takes the bump against Dustin May on Sunday Night Baseball between the Yankees and the Red Sox. The Red Sox hold the first AL Wild Card seed; the Yankees hold the second. Both trail the Toronto Blue Jays in the AL East, and the Mariners are dogging New York’s tails. And New York’s dogging Boston’s. While the Red Sox have already claimed a series win, the Yankees are hoping to save face on national television tonight.
Check out all the options available on the MLB page of DK Sportsbook. Below’s a thorough look at my favorite bets for the Yankees vs. Red Sox game on Sunday night.
Best Bets for Red Sox at Yankees on 8/24/25 on DraftKings Sportsbook
Trent Grisham to hit a home run (+400)
Grisham draws Dustin May, whose contact profile leans heavy sinker/slider and keeps him around the zone long enough for lefty pull damage in the Bronx. Grisham’s power plays to the short porch, and he’s locked into leverage ABs batting behind traffic. New York stacks baserunners because Aaron Judge refuses to give away plate appearances; he’s sitting on a .327 average, 40 homers, and 104 RBI this season, forcing pitchers into stress counts all night (2025). The matchup context helps: we’re confirmed for Carlos Rodón vs. Dustin May under the lights, so I’m pricing a righty starter feeding a lefty bat in a park that punishes even modest loft to right.
The market already tipped its hand—DraftKings hung +400 on Grisham to leave the yard—so I’m buying into the number and the swing path that profiles for pull-side carry. Judge’s elite run-production environment deepens the pitch-to-hit quotient for everyone behind him; his bases-empty wRC+ sits at a cartoonish 206, and it’s still 182 with men on, so protection and table-setting never sag (2025 splits). I want a one-swing cash with a live bat in a righty matchup, and this is the cleanest ceiling on the board at real plus money.
Aaron Judge to hit a home run (+185)
Can you tell I’m a little bit spooked about Dustin May? I’m buying both the above longshot for a home run bet tonight, and also paying for maximum ceiling on the premier bat in baseball. Judge’s 2025 line still screams lift-off: monster power profile with an ISO at .347, a .674 SLG, and a .450 xwOBA fueling a cartoonish 196 wRC+ (2025). That dominance rides elite zone control, showcased by a .440 OBP that forces pitchers over the plate when behind (2025). Boston hands the ball to Dustin May, whose sinker/slider tunnel still leaves windows up in the zone when he chases early-count soft contact. Judge punishes those windows, especially middle-up and out over, where his leverage and bat speed erase park geometry.
The matchup quality holds across innings because New York stacks lefties and switch threats around him, discouraging Boston from soft landing pockets. On national TV, attack profiles matter; Judge’s power diet doesn’t need perfect timing, only one mistake. At +185, I’m paid appropriately for one ideal swing path against a pitcher still integrating new catchers and run-prevention schemes. This is a green-light swing prop anchored by elite 2025 contact quality and run creation that doesn’t sag late. DraftKings is hanging a premium number; I’m leveraging it with the best one-swing outcome on the board.
Carolos Rodon 8+ strikeouts (+130)
I want ceiling, so I’m skipping the standard line and climbing. Rodón’s 2025 strikeout rate sits at 27.3%, a top-shelf punchout clip that translates cleanly to staircase markets (2025). The shape backs it up: a north–south four-seam that plays above the zone and a wipeout slider that shreds two-strike aggression. Boston’s revamped heart is contact-driven but still exposed when forced behind in counts by early heaters. Rodón’s game scripts with leads let him chase Ks, not manage contact; New York’s lineup gives him that cushion almost nightly. Seven is a fair demand, not a dream, given workload and pitch mix usage in spotlight starts. The Red Sox will see him tunnel fastball/slider repeatedly; the second time through is where whiffs stack when hitters cheat.
At +130 on DraftKings for 8+, I’m buying a single extra strikeout for a meaningful price bump rather than laying juice on the main line. If he sits on the edge all night, we still get multiple paths: early chase, third-time-through expansions, and a bullpen that won’t rush the hook if he’s cruising. The math, the pitch shapes, and the role all converge at eight.
