It’s been an odd start to the season for the usually mighty AL East.
The Red Sox are struggling. The Blue Jays are struggling. The Orioles are struggling. And it’s not even like the teams have been playing each other. This isn’t a product of cannibalization. There’s just been some bad baseball.
Rising to the top of this mess has been the Yankees, who have not been hitting as well as you’d expect, but who have gotten enough pitching to surge out to a 13-9 record and the division lead. However, will they be able to hold onto that crown after a visit to the always difficult Fenway Park?
Let’s preview this historic rivalry and make a couple picks on the DraftKings Sportsbook.
Yankees vs. Red Sox prediction, preview
If there has been one black spot in the Yankees’ rotation, which owns an AL-low 2.98 ERA, it’s been Luis Gil. The former Rookie of the Year has struggled since making his season debut back on April 10, with a 9.36 FIP across 9.0 innings of work. Gil’s last start was particularly troublesome. In five innings against the Angels, the right-hander surrendered three home runs, while 10 of the 15 batted ball events he induced were hard hit. In the past, Gil could negate some of these contact-oriented woes with a heavy dose of strikeouts, but that skill doesn’t appear to be in his toolbox anymore. Gil’s swinging strike rate has fallen from 11.7% in 2024, to 8.7% in 2025, to 6.4% in 2026. It’s a unnerving trend, and one that will likely see Gil on the outside looking in when Carlos Rodon and Gerrit Cole are healthy enough to return to MLB.
Still, it’s not like it would be impossible for Gil to put together a solid outing against these Red Sox. Where New York can mostly place the blame for its slow start to a .256 BABIP — this is a roster that boasts still the American League’s highest ISO (.192) and expected wOBA (.347) — Boston has underwhelmed on the scoreboard in 2026 for more concrete, sustainable reasons. The Red Sox’s .112 ISO ranks 29th in MLB and it’s completely backed up by a league-worst .364 expected slugging percentage. This is what can happen when you lose Rafael Devers and Alex Bregman, then see below-average results from Jarren Duran and Roman Anthony. That’s not to suggest that a player with Anthony’s incredible talent can’t get better, yet a lack of launch angle optimization has been the uber prospect’s red flag for awhile now. His 1.67 GB/FB ratio needs to improve before he’s a consistent power threat.
Fortunately, some Boston prospects are thriving at the moment. I’m talking, of course, about Connelly Early. Is there a little hesitation about the left-hander regressing to towards his 5.24 xERA? Definitely. Early will need to shore up an 11.9% walk rate, especially when it gets warmer, and a 17th percentile opponent barrel rate (13.5%) starts to lead to a few more home runs. All that said, Early’s 24-years-old with a 2.31 ERA and a 2.26 FIP in eight career starts with the Red Sox. He’s got a 30.1% strikeout rate and an upper 90s fastball. How much more can you ask from this guy?
Yankees vs. Red Sox pick, best bet
Best Bet: Yankees ML (+104)
Just feels like a good spot to back the Yankees as a dog. Gil’s ineffectiveness and the Red Sox’s offensive woes are a wash, while Early’s due for a little regression. That will likely happen on Tuesday against New York’s lineup full of boppers.
Strong Lean: Aaron Judge 2+ Total Bases (+105)
Judge has six home runs in his last eight games. In fact, all eight hits Judge has in that span have gone for extra bases. His .525 expected wOBA against LHPs is the highest mark on the Yankees in 2026.
