Just a few years ago, if you had told Chicago White Sox fans that first baseman Andrew Vaughn would hit a towering, game-tying three-run home run in the Division Series, nobody would have batted an eye.

Of course, they also would have assumed that Vaughn had finally tapped into his power and established himself as a force in the middle of the lineup for the Chicago White Sox — the trajectory he was supposed to be on.

But no. Vaughn’s clutch home run on Monday night came as a member of the Milwaukee Brewers, as did the most successful season of his professional baseball career so far.

A miserable start to the 2025 season pushed GM Chris Getz to pull the plug early, shipping Vaughn to Milwaukee in exchange for starting pitcher Aaron Civale. Ironically, Civale now finds himself with the Chicago Cubs — the very team Vaughn tormented throughout his breakout season, never more so than on Monday night.

If you’re a Sox fan hoping for a quick Cubs exit from the 2025 postseason, there’s a small silver lining in Vaughn’s surge. His .869 OPS with the Brewers after the trade carried Milwaukee’s offense through key injuries and fueled a 17-7 month of July. Now, in October, his three-run homer was part of seven unanswered runs that put the Cubs in a 0–2 hole in the NLDS — one loss away from elimination.

Still, for White Sox fans, watching Vaughn succeed elsewhere is bittersweet. This is the hitter many envisioned anchoring the South Side lineup for the next decade. This is the clutch bat that was supposed to take the torch passed down from Frank Thomas, to Paul Konerko, to José Abreu.

As the White Sox look to turn the corner as a franchise, there’s plenty to like about the young core taking shape. Kyle Teel, Colson Montgomery, and Chase Meidroth all look like legitimate big leaguers. But one glaring hole remains: power. The Sox don’t have a long-term answer at first base — though Miguel Vargas and Lenyn Sosa could get a shot and take the next step in 2026.

Just imagine if Vaughn had figured it out in Chicago. If the hitter he’s become in Milwaukee had emerged in a White Sox uniform. He didn’t need to hit 40 or 50 home runs — even 25 or 30 with the ability to deliver in big moments would have changed everything. That kind of presence would have stabilized the heart of a lineup that’s lacked identity since Abreu’s departure.

Instead, Vaughn’s redemption arc is unfolding 90 miles north at American Family Field. His breakout is a reminder of what the White Sox once believed they were building — and what slipped through their fingers.

It’s the cruel poetry of baseball: sometimes the talent you develop becomes the lesson you have to learn from, not the player you get to win with.