Yankees' Mark Leiter Jr. trade suddenly looks better after latest Cubs-White Sox move

Midway through Mark Leiter Jr.'s search for a low point last September, it seemed like the Chicago Cubs had bested the New York Yankees in another trade, no matter the outcome on their side. The Hayden Wesneski-Scott Effross deal was already residing on Infamy Boulevard at that point (Wesneski was eventually flipped for Kyle Tucker), and both infielder Ben Cowles and reliever Jack Neely seemed like potentially useful pieces for the Cubbies.

Cowles opened 2025 as the Cubs' 22nd-ranked prospect, per MLB Pipeline, and the team's plans included penciling him in to an eventual utility role. Those plans, as plans often are, got shredded.

The versatile 25-year-old was solid this season, hitting nine homers and driving in 44 runs with a .686 OPS at Triple-A Iowa City, but failed to match the heights he reached last year, with an OPS of .848 in Double-A Somerset (and just four games playing in the Cubs' system, post-trade, due to injury).

After watching 100 games of Cowles, the Cubs deemed four weeks of Carlos Santana more valuable to their program overall, DFAing the ex-Yankee to make room for a veteran presence at first base ahead of the playoffs. The White Sox jumped on Cowles and claimed him Wednesday, adding him to their crowded infield mix at Triple-A Charlotte.

Former Yankees product Ben Cowles from Mark Leiter Jr. trade DFA'd by Cubs, goes to White Sox

Neely, too, has struggled this season. The mustachioed reliever, who we argued would've done more for the Yankees last year as a raw rookie than the fish-out-of-water Leiter Jr., posted a 9.00 ERA in six games with Chicago in 2024, and has a 6.91 ERA in 24 games at Triple-A this season. He's currently on the mend from a mysterious injury, and his grip on a 40-man roster spot is almost as tenuous as Cowles'.

Meanwhile, Leiter Jr. shrugged off his implosion last summer to have a solid postseason, with a 3.86 ALCS ERA and a clean sheet 0.00 mark in four World Series outings. He holds a 4.22 ERA in 52 games this year, and is controlled through 2026. The rest of his Yankees story remains unwritten, as Cowles' time on the North Side of Chicago comes to an end (before he even debuted).