White Sox Face Critical Rebuild: Examining Free-Agent Pitching Options

This analysis takes into account the usual fiscal constraints associated with a team owned by Jerry Reinsdorf, with approximately 25 potential names under consideration.

I've categorized available free-agent pitchers into five distinct archetypes: Top-Tier, Washed-up, Reclamation Projects, End of the Roads, and Not Good, providing a full-scope evaluation of potential arms to help the White Sox' pitching situation.

Removing most of these top-tier candidates from your offseason wish list is prudent. Firstly, they are the most sought-after players on the market and are inclined to join competitive teams, which the White Sox are not, regardless of what the front office may say. Playoff contenders will prioritize these pitchers to fortify their rosters for postseason success.

Furthermore, most high-end hurlers will demand the kind of hefty contracts that the White Sox are unlikely to dish out.

The Best and Unlilkely

NL Cy Young frontrunner Blake Snell is the premier choice in the pool of available options. Snell, a left-handed pitcher, is entering his age-31 season. In 2023, the southpaw tossed 180 innings, the most he's pitched since he earned the 2018 Cy Young Award with Tampa Bay. This marks a significant departure from his lower innings totals in previous seasons.

Nonetheless, he remains the most coveted prospect in the market, likely commanding a contract exceeding $100 million from a contender.

Jordan Montgomery is another pitcher that White Sox fans can exclude from their considerations. On the verge of turning 31, the left-hander has demonstrated impressive durability by making at least 30 starts in the past three seasons. He has compiled a 3.48 ERA and 1.18 WHIP in that span.

Given his blend of endurance, ability, age, and recent playoff performance, he will likely secure a substantial contract with a competitive team.

Sonny Gray, a candidate for the AL Cy Young Award, delivered a stellar performance for the Minnesota Twins, helping them advance in the playoffs for the first time since 2002. Despite being 33 years old and contemplating retirement, if he decides to prolong his pitching career, he's likely to secure a contract exceeding $20 million annually with either the Twins or another contender.

Aaron Nola contributed another remarkable postseason outing, helping the Philadelphia Phillies in eliminating the Miami Marlins. While Nola experienced a less impressive regular season, his track record of past achievements and resilience is undeniably excellent. As a homegrown talent, drafted by the Phillies in the first round in 2014, he has compiled a 3.65 ERA across 175 starts over the past six seasons.

Like several of his free-agent peers, Nola will land a contract with an annual value of at least $20 million, and it would be surprising if he doesn't remain with Philadelphia in 2024.

Maybes

Another option for the South Siders' rotation could be Michael Wacha, who has delivered an ERA in the low threes over the past two years. However, it's worth noting that he did so in fewer than 25 starts. Now, at 33, Wacha and the Padres possess a mutual option for $16 million with a club option for 2025. In the 2024 season, they must pay Wacha $7 million, provided either party exercises the opt-out clause.

Given he's approaching his 34th birthday, Wacha might aim to secure his final guaranteed multi-year free-agent contract. A comparable deal is that of Miles Mikolas, who signed a three-year contract worth $55 million with the St. Louis Cardinals at the age of 34.

From a financial standpoint, this aligns with the White Sox' interests. However, acquiring a 34-year-old pitcher may not be wise for a team amid a rebuilding phase.

White Sox fans are well aware of Lucas Giolito's abilities. Still, a disappointing 2022 season and subpar 2023 showings with two different teams post-trade deadline may have adversely impacted his chances of inking a lucrative contract. Despite being a durable pitcher with youth still on his side at 29 years old, the recent two-year performance dip could lead him to opt for a short-term "prove-it" deal with an early opt-out clause.

A reunion with the right-handed pitcher appears improbable, especially given previous disagreements with the White Sox, including a contentious dispute over a mere $100,000 that nearly led to arbitration. However, Ethan Katz, set to return to Pedro Grifol's staff, and Brian Bannister in the fold could help Giolito return to form and re-enter free agency in better standing.

The Most Likely

Conversely, a reunion with Mike Clevinger appears more realistic. Clevinger faces challenges that may hinder him from earning a contract as lucrative as others in the market. He has an extensive injury history and is approaching his 33rd birthday next year. Despite these hurdles, his strong performance after returning from a two-month injured-list stint in 2023 suggests he will earn a multi-year deal.

A comparable situation can be found in Drew Smyly. At the age of 33, the left-hander signed a similar contract with the Chicago Cubs, inking a two-year pact worth $19 million, aligning with the White Sox's financial range.

Completing the remainder of the list is Kyle Hendriks, and his presence here might raise eyebrows, yet the remaining choices inspire little confidence. Hendricks has demonstrated durability throughout his career and made a solid recovery following an injury-plagued 2022 and a lackluster 2021.

However, heading into his age-34 season with just 137 innings pitched in 2023, it's unlikely he'll get a lengthy contract. His teammate, the aforementioned Smyly, represents a comparable contract reference.

From a financial perspective, this aligns with the White Sox' budget and rebuilding timeline. Hendricks' potential upside lies in his ability to serve as a seasoned mentor for the incoming wave of minor-league pitching prospects.

Should Hendricks continue to build upon his 2023 performance, the White Sox could also draw value from this acquisition come the trade deadline.

What's On Tap Next?

Stay tuned for the next part of this series, in which we will discuss long-time veterans that could fulfill back-end starter roles for the White Sox' 2024 rotation.