​Less than 24 hours before the 2026 MLB Draft kicks off, the Pittsburgh Pirates pulled off a high-profile trade involving one of the top draft selections. The deal with the Chicago White Sox sends Pittsburgh’s Competitive Balance Round-A pick (No. 34 overall) and left-handed pitcher Jaden Woods to Chicago, in exchange for infielder Jacob Gonzalez (the White Sox’s No. 28 prospect) and left-hander Brandon Eisert. The move comes after reports Friday that the Pirates were listening to offers and open to trading the compensation pick, and now they have moved it in a way they believe will help their immediate roster.
“We believe in this team, and we discussed multiple ways to use the compensation pick to strengthen it,” Pirates general manager Ben Cherington said in a team release. Gonzalez has appeared in 30 games for the White Sox in the majors this season, posting a .244/.323/.360 batting line with six extra-base hits in limited action. In a larger sample size that includes two seasons at Triple-A, the 24-year-old carries an .882 OPS. The acquisition gives Pittsburgh an infield option who can contribute right away, particularly in light of Konnor Griffin’s injury, which could sideline him until at least mid-September and possibly the rest of the season.
“Jacob Gonzalez can complement Nick Gonzales and Jared Triolo on the left side of the infield in Griffin’s absence,” explained the Pirates’ front office. “He’s also a versatile, left-handed hitter who has taken meaningful strides this season, and we believe in him for the long term.” On the mound, Eisert has appeared in 25 games, four of them starts, in 2026. His numbers in those outings include a 5.93 ERA and a 1.24 WHIP, along with a 27.4 percent strikeout rate (ranking in the 80th percentile) and a 31.2 percent whiff rate (88th percentile). Cherington added, “Brandon Eisert strengthens our depth in left-handed relief.”
The Pirates will need to make a corresponding roster move to clear a spot on the 40-man, but that decision was not announced as of Friday night. This trade marks a bold use of the compensation pick to bolster a team that is trying to contend now, rather than waiting for development alone. Gonzalez provides a left-side option who can be in the mix immediately, while Eisert adds depth to a bullpen that could benefit from improved left-handed versatility as the stretch run approaches.
As the 2026 draft looms, Pittsburgh’s willingness to leverage the No. 34 pick signals a clear intent to upgrade the roster in real time, balancing optimism about future prospects with a present-day push to strengthen the big-league club. The White Sox, meanwhile, add potential infield depth and a left-handed bullpen option, pairing a pair of players who could contribute soon with a foundational talent on the infield in Gonzalez. It’s a transaction that reflects careful evaluation of both teams’ needs, with the Pirates aiming to maximize the immediate impact of their compensation pick and the White Sox adding a versatile piece for their minor league and major league depth charts.