Why The White Sox Signing This Pitcher Makes Too Much Sense

The White Sox had a significant improvement from 2024-2025, as they won 19 more games this past season. This was solid progress, as they looked like a much more competent baseball team. This improvement was due to a lot of factors, but most importantly, contributions from their top prospects.

This sets the White Sox up for continued improvement throughout the organization in 2026, as they will have the number one draft pick come July, as well as the flexibility to add players from outside the organization. After already adding Munetaka Murakami, Anthony Kay, and Sean Newcomb in free agency, the White Sox have filled some of the bigger holes on the roster. However, there is still some work to be done, as they could use another outfielder and a few more arms.

Thankfully for the White Sox, there are still a lot of quality free agents available as we approach the new year. I am not sure if the White Sox have another big free agent up their sleeve, but I can certainly see them adding a few more solid players.

One of the players they should look into is starting pitcher Jordan Montgomery, most recently of the Milwaukee Brewers. Montgomery, now 33, missed the 2025 season due to injury, but has been a productive player throughout most of his major league career.

In total, Montgomery is a career 4.03 pitcher over 872 major league innings. He has struck out 788 batters and has a solid 1.2 WHIP. Additionally, he is a lefty, which can help balance out the right handed majority that currently makes up the White Sox rotation.

Jordan Montgomery has two strikeouts tonight. They’re both against Yordan Alvarez pic.twitter.com/JCgeKtr6Cc

— Talkin' Baseball (@TalkinBaseball_) October 16, 2023

Montgomery had his best season in 2023, as he had a 3.20 ERA over 188 innings, striking out 166 while only walking 48 batters. This led to him signing a one year, 25 million dollar deal with the Arizona Diamondbacks.

That deal didn’t pan out, as Montgomery had his worst major league season, throwing 117 innings of 6+ ERA baseball. He would then miss the entire 2025 season due to a UCL injury. This lead to the Diamondbacks trading Montgomery to the Milwaukee Brewers at the 2025 deadline, as part of a salary dump.

Now, Montgomery looks to bounce back and the White Sox could be the perfect club to do it with, as they could use a veteran presence in the rotation who can eat up some quality innings. Outside of his rough 2024 season, Montgomery has pretty much had a sub 4 ERA in every full season he’s played.

The White Sox should bet on him to return to that form, and Montgomery could use these innings to rebuild his value heading into 2027, as he could get a more lucrative deal. Coming off a rough 2024 season and a UCL injury, Montgomery’s price tag won’t be too high, so he could be a very solid buy-low signing for the White Sox.