With less than six weeks to go until the postseason and the New York Yankees holding a nine-game lead for the first American League wild card spot, it would be fitting for the team’s attention to shift to October. However, as tempting as that might be, two Yankees know that their play down the stretch will decide whether they don pinstripes in 2027.
Trent Grisham
Originally the throw-in piece from the infamous Juan Soto trade of 2023, Trent Grisham broke out in 2025 as the Yankees’ starting center fielder. In 143 games, the former first-round pick posted career highs in hits (116), home runs (34), RBI (74), walks (82), OPS (.811), and WAR (3.5). As a result, he seemed primed for a big October.
Unfortunately, that big month never came. In 29 postseason at-bats, Grisham struck out in 10 of them, posting a .138 batting average and .426 OPS. The Yankees ultimately fell to the Toronto Blue Jays in the ALDS in four games.
In the offseason, Grisham accepted the Yankees’ one-year, $22.5 million qualifying offer to return to the Bronx. However, his 2026 season has been marred by inconsistencies. The highs have been high, as Grisham hit .361 in June and boasts a .968 OPS with six home runs in August. Unfortunately, the lows have been equally low, with Grisham batting .132 in April and .165 in July.
Most frustrating, though, has been his defense, the part of his game that’s regressed the most since his Gold Glove seasons in 2020 and 2022. In 2026, Grisham has posted -5 outs above average, a mark that ranks in the 10th percentile. His fielding run value of -3, meanwhile, ranks in the 24th percentile.
Jazz Chisholm Jr.
While Grisham has dealt with inconsistency, Jazz Chisholm Jr.’s season has yet to get off the ground. Through 117 contests, the 27-year-old is slashing .216/.296/.385, all career lows since his 2020 rookie season.
His defense remains elite, as his eight outs-above-average ranks in the 95th percentile. Unfortunately, that alone might not be enough, especially considering his questionable antics. For example, during a June 22 contest against the Detroit Tigers, Chisholm Jr. played second base with a lollipop in his mouth, a display that left many Yankee fans frustrated.
In addition, Chisholm Jr.’s brash demeanor has come back to haunt him. After telling reporters he planned to join Los Angeles Dodgers two-way star Shohei Ohtani as the second member of the 50/50 club, it’s reasonable to think he won’t eclipse the 20-home-run mark.
Like Grisham, Chisholm Jr.’s current contract expires after 2026, as the 2025 Silver Slugger will become an unrestricted free agent.
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