White Sox Free Agent Target: Jack Flaherty

The White Sox will have a few holes in the rotation this year. As of right now, most of the rotation is up for grabs. Assuming Dylan Cease will not be on the roster come the start of the 2024 season, there are just a few options currently on the active major league roster. We also don't know what the White Sox plan is with Michael Kopech, so that adds more ambiguity.

With that being said, I can see the White Sox targeting some bounce-back arms to compete with the acquisitions from the Braves, the younger arms in the upper minors, and guys like Davis Martin and Touki Toussaint. You can never have too many arms, and if they pitch well, you can trade them midseason to bolster the rising prospect pool.

One of the arms they should target is Jack Flaherty. He has a connection with pitching coach Ethan Katz, as he was at Harvard-Westlake High School when Katz was the pitching coach. This is a connection in which you could see Katz push to get an arm like Flaherty, as he has worked with him in the past and could tweak some things to bring him back to his best seasons.

Flaherty will be 28 for the entirety of the 2024 season, so he is still young and entering the prime of his career. He came into the league in 2017 and was 5th in Rookie of the Year voting in 2018. He followed up that great season with a stellar 2019 campaign.

In 2019 he had a 2.75 ERA in 196 innings. In those innings, he had a league-leading .9 WHIP and struck out 231 batters. He also led the National League in hits per nine innings, as he averaged a fantastic 6.2. He would finish 13th in MVP voting and 4th in Cy Young. A tremendous season, but he has yet to have that same success since then.

He has not necessarily been bad from 2020-2022, as he has had some respectable years, but he has struggled to stay on the field. Last year he was mainly healthy and it was not the best year for him. He would have an okay year with St. Louis before being traded to Baltimore right before the deadline. Things just did not work out for him in Baltimore, as he had a 6.75 ERA in seven starts for the Orioles.

This makes Flaherty a prime bounce-back candidate. Due to his past successes teams will be interested, but his price won't be too high due to his 2023 season. This is where the White Sox could slide in. Katz is very familiar with him, and Katz worked well with Giolito, so it could be some of the same success in this case.

At worst, he is a back-of-the-rotation arm that can eat innings while the White Sox wait for their top pitching prospects. At best, he shows flashes of his 2019 self and can either sign an extension with the Sox, or they could trade him at the deadline and they could get a few good prospects. This is a very low-risk signing they need to look into.