TST Best Bets: July 24, 2027
Timothy Hessen
Host · Writer
With the MLB trade deadline just 10 days away and playoff races beginning to tighten across the league, four winning teams open important three-game series against one another this weekend.
The Chicago Cubs begin a road series with the Pittsburgh Pirates, as four and a half games separates them from second and third place in the NL Central.
Meanwhile, the New York Yankees, who are still without Aaron Judge and Giancarlo Stanton, are looking to narrow the slim gap between themselves and the Tampa Bay Rays for the top record in the American League.
To do that, they’ll need to perform well against a Philadelphia Phillies team that has gone 37-17 since April 28 and currently sits in an NL Wild Card position.
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First Pick: Chicago Cubs ML (-105) over Pittsburgh Pirates
Rundown: Pittsburgh struggled against New York in its last series, and while this homestand against a division rival presents a strong bounce-back opportunity, the opener does not project as the Pirates’ best chance to win.
Matthew Boyd gets the start for the Cubs tonight, and although his overall season numbers are underwhelming, the southpaw has been excellent since returning from injury last month, posting a 2.57 ERA across five starts.
The Pirates have one of the biggest discrepancies in baseball against right-handed and left-handed pitching this season, going 44-30 against righties but just 9-20 against lefties.
Expect Friday to represent Chicago’s best opportunity to pick up a win in this series.
Second Pick: New York Yankees ML (+121) over Philadelphia Phillies
Kim Klement Neitzel-Imagn Images
Mar 22, 2026; Tampa, Florida, USA;New York Yankees infielder Ryan McMahon (19) hits an RBI single during the fourth inning against the Philadelphia Phillies at George M. Steinbrenner Field.
Rundown: New York’s status as an underdog is a bit surprising given Philadelphia’s slow start coming out of the All-Star break.
The Phillies are only four and a half games behind the Atlanta Braves in the NL East, but their minus-15 run differential suggests they have not played quite as well as their record indicates. Meanwhile, the Yankees lead the league in ERA and own a plus-88 run differential.
Philadelphia has also struggled at the plate, hitting just .222 against right-handed pitching in July and .202 over its last 10 games.
With the Phillies’ offense still searching for answers, don’t expect that cold stretch to end in the series opener.
