White Sox worst enemy is the perfect fit to join them as a free agent this offseason

Following the MLB trade deadline, Chicago White Sox GM Chris Getz indicated to the media that the club would be open to adding in free agency this winter. 

Surprisingly, the perfect free agent fit for 2026 might be the franchise’s current worst enemy. 

With the White Sox turning a corner and playing more competitive baseball in the second half of the season, it may be time for Chicago to initiate the next phase of the rebuild and bring in a few veteran players as building blocks. 

I’m not delusional about what’s realistic for the White Sox. They’re not going to go out and sign a frontline starting pitcher or five-tool outfielder for $100 million+. This is certainly not the offseason for the White Sox to go “all in” and make a big splash.

It just makes sense for Chicago to address some of their bigger positional needs in free agency to put a more well-rounded team on the field. This young core needs to learn how to win, and one way to ensure that happens is by bringing in winning players who compliment them well. 

Looking at the team’s biggest needs, signing a veteran power bat would seem to make sense, especially a primary first baseman and designated hitter. 

Andrew Vaughn flamed out and was traded to the Milwaukee Brewers. Tim Elko hasn’t had success at the big league level. Miguel Vargas and Curtis Mead are both high-upside players, but both can play third base or DH next season. They wouldn’t be losing at-bats by bringing in a more bona fide power hitter. 

Ironically, White Sox killer Josh Naylor is a free agent and fits all of the team’s biggest needs while still being in their price range. 

Josh Naylor is the White Sox worst enemy

The rivalry between the White Sox and Josh Naylor dates back to his time with the division rival Cleveland Guardians. 

Back in 2022, with the White Sox leading Cleveland 8-4 in the ninth inning, Naylor launched a two-out, game-tying grand slam off of closer Liam Hendriks. He followed it up with a game-saving scoop at first base in the night and a go-ahead three-run shot in the 11th inning. 

Naylor became the first player in MLB history to record 7+ RBIs in the ninth inning or later of a game. He screamed at White Sox fans that were chirping him following his second blast, which turned into a viral video. 

No player has more RBIs than Josh Naylor against the Chicago White Sox since 2022. It’s not particularly close, either. Combine that “White Sox killer” production with Naylor’s fiery personality, and you’ve got a guy that’s easy for the South Side faithful to loathe.

In his career against the White Sox, Josh Naylor is batting .353 with 11 home runs, 42 RBIs, and a 1.012 OPS. 

Naylor burned the White Sox again this week. In each of the first two games of this week’s series between the Sox and Mariners, Naylor hit a home run, recorded multiple hits, and stole multiple bases. 

He bat flipped when he launched his home run on Tuesday night, and his home run off Jonathan Cannon on Wednesday was the longest of his career, traveling 450 feet.

Naylor is a perfect free agent fit for the White Sox

The White Sox need to add a little power to their lineup in the offseason. Naylor would bring 20-30 home run power, a knack for clutch hitting, sneaky athleticism on the bases, and energy to a young White Sox team. 

Naylor probably won’t get $100 million on the open market, but I think a four-year, $70 million contract is more than fair for a 28-year-old first baseman with his production.

It would solve an immediate need, but also give Chicago an experienced power bat to lean on well into their targeted contention window.

Besides, we already know Josh Naylor loves hitting at Rate Field. If it was his home ballpark, we could see his 31 home runs in 2-24 become par for the course. 

They say “if you can’t beat them, join them.” But in this case, if you can’t beat them, sign them. The best option for the White Sox in free agency might be dishing out a big contract to their current worst enemy, in which case, I’m sure Naylor would become an immediate fan favorite.