Which Impending Free Agent Bats Have the Most To Gain in October?

October baseball: where contenders immortalize themselves as champions, where great players cement themselves as icons of their franchises, and where impending free agents have the ultimate stage to elevate their value and turn a few weeks of October magic into millions of dollars on their next contract. 

Playoff baseball has long been a land of opportunity for big league players. The peaks and valleys of the regular season stat line have finally faded into the rearview mirror, and suddenly, the canvas is blank once again. Every pitch carries more weight, every swing means more, and every performance has the opportunity to reshape how a player is remembered and valued. 

In the past decade, Major League Baseball fans have had the privilege of watching postseason heroics from numerous players on the cusp of entering the open market, turning October into the ultimate audition for their next contract.

From Nathan Eovaldi’s courageous extra-inning performance in Game 3 of the 2018 World Series, to Walker Buehler’s six shutout innings in the 2024 World Series, and who could forget Jorge Soler’s mammoth home run in the 2021 World Series that may never have landed?

Each of those performances resulted in the players being lionized in a franchise’s history books, but also undoubtedly led to an increase in their value as they entered free agency shortly after season’s end.

As the 2026 baseball season approaches its postseason, it is worth taking note of some big league players who we believe will have an excellent opportunity similar to the likes of Eovaldi, Buehler, and Soler: a chance to maximize their earnings this offseason while potentially becoming a hero for their current ballclub.

For some, the upcoming postseason could represent more than a chance to compete for a championship—it could be their final games in the place they have called home, giving them one last opportunity to leave a lasting mark before entering free agency.

This article is one in a two-part series. You can read about impending free agent pitchers here. All statistics as of September 8.

Luis Robert Jr. 

There are not many players in professional baseball who leave you wanting more than Luis Robert Jr.

The Cuban outfielder was once one of the most highly touted prospects in the game, and the Chicago White Sox envisioned him as the centerpiece of their youth movement in the late 2010s and early 2020s.

Robert was the focal point of a young core that included Yoán Moncada, Michael Kopech, José Abreu, Garrett Crochet, Tim Anderson and others. Some of those players went on to find immense success in the majors, while others never quite reached the heights once expected of them. Nobody better embodies the peaks, valleys and unfulfilled potential of that era of White Sox baseball than Luis Robert Jr.

Robert made his major-league debut during the pandemic-shortened 2020 season and immediately flashed the talent that had made him such a coveted prospect. At just 22 years old, he finished second in American League Rookie of the Year voting and won a Gold Glove.

Over the following two seasons, Robert continued to produce, posting an .830 OPS and showing the makings of a star-caliber center fielder. The catch, however, was that he could not stay on the field. He failed to eclipse 100 games in either season, as injuries repeatedly interrupted his development.

Still, when healthy, Robert continued to give White Sox fans and the organization glimpses of the superstar they believed he could become.

Then came 2023. Robert finally put everything together, appearing in 145 games while posting 5.3 bWAR and launching 38 home runs. After years of waiting, the former top prospect had seemingly arrived. At 25 years old, Robert looked poised to become a perennial All-Star and perhaps even a future MVP candidate.

For a franchise that had spent years waiting for its young core to fulfill its promise, it appeared that Robert was finally becoming the centerpiece Chicago had always envisioned.

Unfortunately for White Sox fans—and for Robert himself—that season remains the last time he has played at an elite level. Over the next two seasons, his defensive impact diminished considerably, making the Gold Glove from his rookie season feel like a distant memory.

The injury bug also returned, turning his healthy 2023 campaign into something that increasingly looked like an outlier rather than the beginning of a new normal. At the plate, Robert regressed as well, producing below-league-average offensive numbers and failing to reach a .700 OPS in either 2024 or 2025.

Robert entered 2026 on the cusp of free agency, playing out the final season of the six-year contract he signed with Chicago in 2020. He also entered the season wearing a new uniform, having been dealt to the New York Mets just before Opening Day.

The change of scenery carried with it a hope that Robert could rediscover the player who had looked like a budding superstar only a few years earlier. Instead, more of the same followed. Robert struggled to recapture his 2023 form and once again battled injuries, leaving him seemingly headed toward the open market with an uninspiring final campaign and the likelihood of underwhelming offers.

But all of that has the potential to change.

On August 31, Robert was claimed off waivers by the Baltimore Orioles, suddenly giving him an opportunity he desperately needed: meaningful October baseball. The Orioles are still alive in the American League Wild Card race, and Robert now has the chance to become a part of a postseason push at precisely the moment when his free agent value is most in need of a boost.

For a player whose career has been defined by tantalizing flashes of brilliance surrounded by inconsistency and injury, October offers an opportunity to rewrite that narrative.

A few weeks of the 2023 version of Luis Robert Jr. could be worth tens of millions of dollars. A memorable postseason could give potential suitors a reason to look past the struggles of the last two seasons and remember the player who once looked like one of baseball’s brightest young stars.

In a sense, October could serve as Robert’s very own Men in Black neuralyzer: a chance to erase the memories of what went wrong and replace them with a final, unforgettable reminder of what he is capable of. For Robert, the road to a new contract may begin with one last opportunity to make baseball forget everything that came before it.

Editor’s Note: Robert was placed on the 10-day IL over the weekend due to a minor hamstring strain. He could return toward the end of September.

Jazz Chisholm Jr.

The MLB: The Show cover athlete for the 2023 season entered his final year of team control as one of the most fascinating free agent profiles to follow.

Jazz Chisholm Jr. is one of baseball’s most volatile personalities, both on and off the field. He is exactly the kind of player a network like ESPN loves to have in front of a camera: charismatic, entertaining and an excellent ambassador for the game.

But that same persona can occasionally produce a headline for the wrong reasons, with Chisholm seemingly capable of delivering at least one off-color comment to the media each season. His volatility, however, is not limited to his personality. On the field, Chisholm has been a player of tremendous highs and frustrating lows.

Chisholm came through the Miami Marlins’ farm system and, like Luis Robert Jr., made his major league debut during the pandemic-shortened 2020 season. Over the next several years, injuries repeatedly interrupted his development, leaving his full-season numbers somewhat underwhelming relative to the immense talent he displayed.

Even with limited action on the field, however, Chisholm remained one of the most electric players in the game. His combination of athleticism, power and speed produced highlight-reel plays on both sides of the ball and quickly made him one of the most recognizable young players in baseball.

Despite his popularity and his ability to produce an electrifying play at seemingly any moment, Chisholm had yet to put together the consistent, full-season production expected of a star. That changed when the Yankees acquired him from Miami at the 2024 trade deadline.

Chisholm went almost overnight from playing in one of baseball’s quieter markets to performing under the brightest lights in the sport, with the expectations that come with wearing pinstripes. And, as Yankees general manager Brian Cashman hoped, Chisholm rose to the occasion.

He has become an important piece of the Yankees’ lineup, providing an ideal combination of power and speed while establishing himself as a legitimate middle-of-the-order threat. Across his time in the Bronx, Chisholm has posted a .773 OPS and earned both an All-Star selection and a Silver Slugger Award, with both honors coming in 2025.

Chisholm’s 2026 campaign, however, has represented something of a step backward. In the first half of his walk year, he posted a .698 OPS and struggled to find his footing at the plate. Since then, though, Chisholm has made significant adjustments and begun to rediscover the player the Yankees have come to rely on, producing a much stronger second half and bringing his overall numbers back to respectable levels.

That ability to respond to adversity in an important season—both for Chisholm and for a Yankees team with championship aspirations—will not go unnoticed by front offices around the league. Chisholm has already demonstrated that when things go wrong, he possesses the talent and resilience necessary to turn them around.

One question, however, continues to loom over Chisholm as he approaches the open market: Can he perform in October?

Across seven postseason series, Chisholm has struggled mightily, batting just .170 and going 15-for-88 at the plate. His inability to translate his regular-season production to baseball’s biggest stage represents the most significant remaining question surrounding his free-agent case.

If Chisholm hopes to secure the kind of generational payday that comes with being viewed as a true franchise player, potential suitors will need to believe that he can be that player when the lights are brightest and the games matter most.

This October, Jazz Chisholm Jr. has the opportunity to turn his greatest question mark into his greatest selling point—and potentially turn a postseason breakout into a life-changing contract.

Editor’s Note: Chisholm was placed on the 10-day IL earlier this week due to a right thumb sprain. It’s not clear if he will be able to return by the end of the regular season, but there is no reason (as of now) to think he won’t be ready to return in October.

Seiya Suzuki

Seiya Suzuki’s profile could hardly be more different from those of the previously discussed Luis Robert Jr. and Jazz Chisholm Jr.

Robert and Chisholm are defined by immense potential and equally immense volatility—the kind of players who leave you constantly dreaming about what a fully healthy, fully realized season might look like. When everything clicks, both have the talent to rank among the best players in baseball. The problem is that their careers have been marked by stretches that fall well short of those tantalizing ceilings, leading their production to stray far from what was hoped of them.

Suzuki, on the other hand, is anything but volatile. Since signing with the Cubs as a 27-year-old free agent out of Japan, he has established himself as one of the steadiest offensive performers in the game.

While he may not possess the same sky-high ceiling as Robert or Chisholm, Suzuki has consistently provided the Cubs with what every team covets: reliable production, year after year. Now, at 32 years old, he is not only in the final year of the five-year contract he signed with Chicago, but he is also posting his most impressive season to date, as he currently possesses a .850 OPS as a middle-of-the-order bat for the Cubs. 

Where Suzuki’s profile lacks, however, is experience on baseball’s biggest stage. His limited postseason resume provides little evidence of how he will respond when the stakes are highest.

In his five seasons on the North Side, Suzuki has appeared in just one postseason run. That opportunity finally came last season in 2025, when he put together an impressive October debut, posting an .863 OPS with three home runs across eight games.

Unfortunately for Suzuki and the Cubs, his production was not enough to extend their run. Chicago was eliminated in the National League Division Series by their division rival, the Milwaukee Brewers, in five games.

That limited postseason experience makes the coming weeks particularly important for Suzuki, as he appears to be on track to garner another opportunity at a postseason run with Chicago, as the Cubs are sitting comfortably in a National League Wild Card position.

As the baseball calendar turns to the middle of September, the opportunity for Seiya Suzuki is less about generating zeroes on his next contract, and more about fortifying his free agent profile and cementing his legacy in Chicago in what could be some of his final days in a Cubs uniform. 

Jake Bauers

Jake Bauers is yet another remarkable example of the magic that manager Pat Murphy and the Milwaukee Brewers seem to possess. A castoff from some of baseball’s smartest organizations—including Cleveland, Tampa Bay, Seattle and the Yankees—Bauers has transformed from a journeyman bench bat into one of the National League’s most productive power hitters and a player on the cusp of a significant payday.

Even compared to Tyler Mahle (who you can read about in the pitcher version of this article), Bauers took an unusually winding path to becoming a legitimate major league contributor. Selected in the seventh round of the 2013 MLB Draft, he was traded twice over the next five years, spending time in the professional systems of Tampa Bay and Cleveland before eventually making his way to the majors.

By 2021, the 25-year-old Bauers appeared destined for a career as a minor league depth piece—someone capable of filling in during an emergency but unlikely to receive a consistent opportunity in the majors. What Bauers needed was a role he could carve out for himself. He found one as a left-handed platoon bat, using his power advantage against right-handed pitching to establish himself as a useful bench weapon.

That approach began to pay dividends in 2023, when Bauers tore through Triple-A with the Yankees, hitting 11 home runs in just 24 games. That performance earned him a call-up to New York, where he delivered mixed results overall but demonstrated legitimate power against right-handed pitching. All 12 of his home runs that season came against righties, while he posted a modest .719 OPS against opposite-handed pitching.

That was enough for Milwaukee to take a chance on him. The Brewers, widely regarded as the gold standard of player development, signed Bauers to a major league contract and brought him aboard as a platoon bat in 2024. Since arriving in Milwaukee, he has seemingly benefited from the organization’s developmental touch, improving his OPS in each season while gradually cutting down on the strikeouts that once limited his offensive value.

Now, in 2026, the final year of Milwaukee’s control over the 30-year-old, Bauers is experiencing the best season of his career. As of mid-September, he has posted a .397 on-base percentage—the best mark in the National League—and leads the Brewers with 24 home runs.

Unlike some of the other names on this list, Bauers isn’t entering October trying to erase a disappointing season or prove that his regular-season success can translate to the postseason. Instead, he is simply trying to prove that his remarkable 2026 campaign is sustainable.

As the competition—and quality of pitching—intensifies down the stretch, Bauers will have an opportunity to show that this season was more than a fluke. If he can continue producing against increasingly difficult competition, the former journeyman could turn an unexpected breakout into a very lucrative free agent payday.