White Sox Trade Jacob Gonzalez for No. 34 Pick in Last-Second Draft Deal with Pirates

The Chicago White Sox pulled off a trade on Draft Night Eve!

With less than 24 hours to go before the MLB Draft officially begins, the White Sox announced that they have added a pick to their arsenal. The organization has acquired Competitive Balance Round A selection – in this case, the No. 34 pick – and southpaw Jaden Woods from the Pittsburgh Pirates. In exchange, they will send over infielder Jacob Gonzalez and reliever Brandon Eisert.

The move makes this upcoming draft even more important for the Sox, who already hold the highly-coveted No. 1 overall pick. They will also select only seven picks later at No. 41 overall, as well as at No. 77, No. 105, and No. 137.

The trade gives the White Sox $20.5 million in bonus pool money, which is a staggering sum that should allow them to add several big-name talents early on Saturday. Even with the organization surging up the AL standings this year, it goes to show how serious GM Chris Getz is about keeping this farm system strong.

White Sox Make Aggressive Draft Trade

Jun 6, 2026; Philadelphia, Pennsylvania, USA; Chicago White Sox shortstop Jacob Gonzalez (7) walks off the field after a victory against the Philadelphia Phillies at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images | IMAGN IMAGES via Reuters Connect

The White Sox have clearly fallen in love with this draft because they paid a relatively hefty price to make this deal happen.

Both Jacob Gonzalez and Brandon Eisert are MLB-caliber players. The former, in particular, is fresh off a successful first stint in the big leagues. Gonzalez is a former Top 15 pick who filled in successfully during the absence of Munetaka Murakami. He hit .244 over his first 30 games with 17 RBIs. While his strikeout rate sat a tad high, there is no doubt he showed enough to warrant another stint in the majors soon. And I guess the Pirates agreed.

Gonzalez was moved back down to Triple-A for a healthy Murakami on Friday, but all indications are that he will now be close to an everyday guy for Pittsburgh. It should be a great opportunity for the Sox' former prospect – one that could certainly have them second-guessing the decision in the future.

At the same time, there is no doubt the Sox' infield is becoming a bit congested. Especially if they do go with shortstop Roch Cholowksy at No. 1 overall, they could find themselves in quite the logjam down the road. Colson Montgomery is currently manning short on the daily, while Chase Meidroth has been a strong option at second.

We also shouldn't completely ignore the fact that the Sox included Eisert. The 28-year-old has struggled to stick in the majors but has displayed good enough stuff to warrant several stints. This included appearing in 73 games for the Sox last season, recording a 4.39 ERA. He can offer several strong offspeed pitches that can force some serious whiffs. It's not out of the question that Pittsburgh can help him turn into a staple bullpen piece.

Nevertheless, the Sox seemingly saw more potential in Jaden Woods. The 24-year-old got promoted to the Pirates' Triple-A system earlier this season after recording a 3.16 ERA for the Altoona Curve. The adjustment, however, hasn't been particularly smooth. Woods has already given up 10 earned runs in just 11.2 innings of work for a 7.71 ERA. Still, there is a lot of swing-and-miss potential with his velo, which is something the Sox have been prioritizing.

So, how should we grade the transaction overall? That might have to wait until after draft day is over. Again, it's undoubtedly a risk for the Sox after the flashes they saw from Gonzalez the last couple of weeks, but they have also shown over the last couple of years that they have a pretty good eye for talent.

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