While the 2026 season may have helped the Chicago White Sox change their league-wide perception and establish a winning culture, there’s still an elephant in the room when it comes to the franchise taking the next step toward contention.

The White Sox remain one of two teams in Major League Baseball history to never sign a contract worth more than $100 million (Athletics). 

Some teams have reached that milestone by signing a marquee free agent. Others have done so by extending a cornerstone franchise player. But the five-year, $75 million deal signed by outfielder Andrew Benintendi before the 2023 season remains the largest contract in White Sox franchise history. And for what it’s worth, it’s not a deal that has aged particularly well for Chicago.

That needs to change. And fast.

20 of Major League Baseball’s 30 teams have agreed to a contract worth more than $200 million, and the White Sox have yet to reach nine figures.

As we look ahead to 2027 and what should be just the beginning of a lengthy contention window for this White Sox team, it’s vital that the front office doesn’t become complacent with the current roster.

Chris Getz cannot rely solely on the development of his young talent as the only source of improvement for his club. The White Sox need to acquire proven, talented veterans, and that’s going to cost money. It’s going to require Chicago to venture into the deeper waters of free agency.

Before diving into an extensive free agency preview, I thought it would be worthwhile to examine five potential targets for the White Sox who could command contracts large enough to become the highest-paid players in franchise history.

Right-handed pitcher Michael King has been one of the most underrated arms in baseball since joining the San Diego Padres in 2024. He’s appeared in 78 games over the last three seasons, posting a 3.15 ERA across 432 innings pitched.

In 2026, King went 12-10 with a 3.21 ERA, and his career 1.86 postseason ERA provides further evidence of his ability to perform on the biggest stage.

King has an opt-out clause in his contract that would allow him to hit free agency this winter. At 31 years old, this could be the perfect opportunity for him to test the market and secure a lucrative long-term deal.

Spotrac’s market value projection has King landing a contract worth nearly $150 million over five years. That would double the largest contract in White Sox franchise history, but it would also give Chicago the reliable frontline starting pitcher it’s looking to add to the rotation.

Freddy Peralta rediscovered himself down the stretch with the Tampa Bay Rays. Over his final six starts of the regular season, the Rays went 6-0, while Peralta posted a 5-0 record with a remarkable 0.79 ERA.

He’s carried that momentum into the postseason, posting a 0.84 ERA across two playoff starts, with Tampa Bay still in the hunt for a trip to the World Series.

Signing Peralta could represent an intriguing buy-low opportunity for Chicago. His value isn’t quite what it was after he led the National League in wins with the Milwaukee Brewers in 2025, but we’ve seen enough over the last two months to believe Peralta is still one of the better starting pitchers in baseball.

And at just 30 years old, he should have plenty of quality innings left in the tank.

Spotrac’s market value projection has Peralta landing a four-year, $110 million contract, but it wouldn’t shock me if he ultimately secured a deal much closer to Michael King’s projected range.

The White Sox should absolutely be players in his market.

The last starting pitcher I want to highlight is former Washington Nationals and Cleveland Guardians left-hander Foster Griffin.

Griffin finished the 2026 season with a 15-6 record, a 3.60 ERA and 172.2 innings pitched between the Nationals and Guardians.

He’s not quite on the same level as Michael King or Freddy Peralta, but he is a left-hander, which could be particularly valuable to the White Sox if they determine Anthony Kay is better suited for a role in the bullpen.

There are some legitimate concerns about how Griffin performed after being traded to Cleveland. The more time he spent in Major League Baseball this season, the more opposing hitters appeared to adjust to him, and his numbers suffered as a result.

But I still believe Griffin is a much better pitcher than the 5.19 ERA he posted with Cleveland would suggest.

With a projected market value of four years and $80 million, Griffin would be a more affordable alternative to some of the other top starting pitchers available in free agency.

Even so, an $80 million deal would still represent the largest contract in White Sox franchise history.

The other area of need White Sox GM Chris Getz has already highlighted is the outfield.

The White Sox want to get stronger defensively, and adding a proven veteran who is athletic enough to provide value in the field while offering balanced production against left-handed and right-handed pitching would make Chicago a much more well-rounded team.

Randy Arozarena fits that description.

Arozarena has hit at least 20 home runs in every season since 2021, and he posted an .865 OPS in 2026, making it the best offensive season of his career. He also established a career high in fWAR while leading the American League in runs scored.

Adding Arozarena to the mix, alongside rising prospects like Caleb Bonemer and the continued development of Chicago’s young core, would lengthen the White Sox lineup and give the team an exciting outlook in the outfield.

Arozarena’s projected market value is currently listed at four years and $80 million, though I believe he could command significantly more than that.

But even if the White Sox were to commit $100 million to Arozarena, it wouldn’t strike me as an overpay for a player with his track record and skill set.

Chicago would essentially be replacing one veteran outfielder in Andrew Benintendi with another who offers more athleticism, greater defensive versatility and a higher offensive ceiling.

That would be a significant upgrade for a White Sox team looking to take another step forward in 2027.

The final option is Seiya Suzuki, a player who has developed into one of the more dangerous hitters in baseball during his time with the Chicago Cubs.

Suzuki has been a model of offensive consistency, particularly over the last four seasons, during which he’s hit more than 20 home runs and posted an OPS above .800 every year. That includes his impressive 2025 campaign, when he hit 32 home runs and drove in 103 runs.

Suzuki also posted a career-high 4.6 fWAR in 2026, thanks in part to improved outfield defense and an increased level of defensive responsibility.

At 32 years old, Suzuki will likely command a contract worth more than $100 million. But if the White Sox are looking to add another dangerous right-handed bat, bring in another Japanese star to complement Munetaka Murakami and improve their overall outfield depth, Suzuki is an intriguing option.

He’s also been vocal about how much he enjoys playing in Chicago, which could make a move across town to the South Side an appealing possibility.

The White Sox certainly aren’t limited to these five options, but I believe this needs to be the offseason in which Chicago makes a splash and sets a new record for the largest contract in franchise history.

Doing so would send a clear message to the fan base that the organization is serious about winning and building on a successful 2026 season that nobody saw coming.

Maybe that investment comes in the starting rotation. Maybe it’s in the outfield. With any luck, it’ll be both.

But these five players are names worth watching as the White Sox enter a pivotal offseason. Each fits the team’s needs and competitive timeline, and each would represent the type of meaningful investment Chicago needs to make to take the next step toward becoming a legitimate World Series contender.