For the first time in over a month, there’s a little unrest in Yankee Land.

New York was swept this past weekend in Milwaukee, while the Rays have won 14 of their past 16 games. That means that Tampa is now leading the AL East. Obviously it’s only May, but as we all know, expectations are always sky high in the Bronx.

Can the Yankees get back on track in Baltimore against the struggling Orioles? Let’s preview this divisional tilt and make a couple picks on the DraftKings Sportsbook.

Yankees vs. Orioles prediction, preview

You pretty much know what you’re getting with Ryan Weathers. The left-hander is a power pitcher who can both rack up the strikeouts, but also get hit hard by right-handed opponents — like, really hard. To wit, Weathers sports a career-high 28.5% strikeout rate in 2026, yet he also owns a 14th percentile opponent barrel rate (11.8%) and a 25th percentile opponent expected batting average (.266). That’s not to mention a fourth percentile expected wOBA on induced batted ball events (.455). To put it plainly, Weathers is at his best when he’s suppressing contact all together, and to be fair, he’s mostly succeeded in that goal in 2026, as he’s registered a 3.03 ERA over 38.2 innings.

The interesting thing on Monday will be to see how Weathers fares seeing the Orioles for a second start in a row. The LHP hasn’t taken the mound since May 2 due to an illness, a day where Weathers was perfectly fine in a 9-4 Yankees’ win. Five innings, three hits (one home run), two walks and five strikeouts. Just fine. In general, you’d think that Weathers sets up fairly well in this specific matchup. Baltimore’s only produced a 95 wRC+ off southpaws this season, as most of the lineup has underwhelmed within the split, with the exception of Adley Rutschman and Taylor Ward. The Orioles aren’t exactly lauded for their ability to make consistent contact, either, as the club ranks top 10 in both strikeout rate (24.5%) and swinging strike rate (11.4%).

This feels like a night where Baltimore’s bats will need to make some noise if the team hopes to keep pace with the mighty Yankees, who lead the American League in ISO (.203) and wRC+ (117). Brandon Young will toe the rubber for the fifth time in 2026, and the 27-year-old doesn’t have much of a track record of success at the MLB level throughout his brief career. Across 16 starts and 78.1 innings, Young has managed a 5.74 ERA and a 5.21 FIP. Most damning, though, is the fact that Young has conceded 1.72 opponent home runs per nine in those appearances. New York leads the league in long balls (63), with Aaron Judge (16) and Ben Rice (12) doing a majority of the damage.

Yankees vs. Orioles pick, best bet

Best Bet: Yankees ML (-163)

Let’s not overthink this. The Yankees have one of the best lineups in baseball and they have a clear starting pitching advantage with Ryan Weathers opposing Brandon Young. They win this game nine times out of ten.

Strong Lean: Over 8.5 (-127)

That said, Weathers isn’t perfect, and his xERA (4.66) suggests he’s due for a little regression. The Orioles should be able to muster two or three runs off the lefty. Expect the Yankees to do the rest.