Predicting the 10 Biggest Contracts Handed Out to 2026-27 MLB Free Agents

The 2026-27 MLB free-agent class has a clear headliner in two-time Cy Young winner Tarik Skubal, but there's a significant drop-off behind him. The class as a whole lacks impact offensive talent.

Michael King, Freddy Peralta and Trevor Rogers are the top pitchers behind Skubal, while Randy Arozarena is the top bat on the market alongside Seiya Suzuki. After a down year, Jazz Chisholm Jr. might have to settle for a short-term, high-AAV deal as he looks to rebuild some value.

There is also a trio of Japanese League standouts in third baseman Teruaki Sato and pitchers Hiromi Itoh and Kaima Taira, who are expected to be posted. All three should command lucrative multi-year deals.

Ahead, we've taken a crack at predicting the 10 biggest contracts that will be handed out to the 2026-27 free-agent class this winter. A lot hinges on how things play out with the impending CBA negotiations and expected lockout, but for now, we'll treat our projections like any other offseason.

Age: 26 Stats: 23 GS, 12-5, 1.36 ERA, 0.96 WHIP, 141 K, 146.0 IP

Used primarily as a reliever in Japan, right-hander Kaima Taira has also previously worked as a starter in 2023 (11-7, 2.40 ERA, 153 K, 150.0 IP) before returning to the rotation with fantastic results this past season.

With a 5'8", 209-pound frame, he might profile best in a bullpen role stateside, where his upper 90s fastball and wide array of secondary pitches could make him a multi-inning weapon or a closer.

Predicted Contract: 3 years, $60 million

The Astros gave Tatsuya Imai a three-year, $54 million deal last winter, betting on his stuff. Taira provides a similarly enticing repertoire. It might not be as straightforward as presented, with opt-outs and potential escalators for starts likely in play.

Age: 32 Stats: 634 PA, 131 OPS+, .270/.368/.473, 58 XBH (26 HR), 3 SB WAR: 5.1

Over the course of his five-year, $85 million deal with the Cubs, Seiya Suzuki posted a 128 OPS+ and 16.2 WAR while averaging 27 home runs and 92 RBI per 162 games.

His .368 on-base percentage in 2026 was a career high. After he was relegated mostly to DH duty while playing alongside Kyle Tucker in 2025, he put together an excellent season defensively (14 DRS, 5 OAA) and is a finalist for NL Gold Glove honors.

Predicted Contract: 3 years, $66 million

A three-year, $66 million deal would match the contract the Dodgers gave corner outfield slugger Teoscar Hernández when he was the same age, though his status as arguably the No. 2 bat on the market could get him a fourth year.

Age: 28 Stats: 30 GS, 10-11, 4.03 ERA, 1.19 WHIP, 157 K, 169.2 IP WAR: 2.2

Trevor Rogers has pitched like a frontline starter at times in his career, including a pristine 1.81 ERA over 109.2 innings during the 2025 season when he finished ninth in AL Cy Young balloting.

His injury history and lackluster 2026 will cap his earning power, but he did toss a career-high 169.2 innings. He finished better than he started, with a 3.52 ERA and 1.05 WHIP in 13 starts after the All-Star break.

Predicted Contract: 4 years, $70 million

The four-year, $68 million deal that Jameson Taillon signed with the Cubs fits the narrative of a talented pitcher who occasionally looked like an ace but often fit better as a No. 3/4 starter.

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Age: 29 Stats: 26 GS, 10-10, 3.18 ERA, 1.26 WHIP, 159 K, 172.2 IP

Right-hander Hiromi Itoh has a strong track record of production as one of Japan's top starters, posting a 2.91 ERA and 1.17 WHIP in 1,008.2 innings over six seasons with the Nippon-Ham Fighters.

While he lacks the swing-and-miss stuff of some other top arms to come out of the Japanese League with a 21.9 percent career strikeout rate, his age, durability and consistency give him a high floor as a potential No. 3/4 starter stateside.

Predicted Contract: 5 years, $75 million

A five-year, $75 million deal would match the contract Kodai Senga signed when he jumped from Japan to join the Mets. He was also 29 years old at the time.

Age: 30 Stats: 32 GS, 10-11, 4.42 ERA, 1.33 WHIP, 156 K, 169.0 IP WAR: 0.7

The Mets paid a steep price to acquire Freddy Peralta from the Brewers last offseason. He took the ball on Opening Day as the ace of the staff. He ended up struggling to a 4.99 ERA and 1.48 WHIP in 113.2 innings and found himself back on the trade block at the deadline.

However, things turned around almost immediately after he joined the Rays. He had a 3.25 ERA and 1.01 WHIP in 55.1 innings to close out the regular season. He has also made two strong playoff starts, including six shutout innings against the Guardians in Game 2 of the ALCS.

Predicted Contract: 4 years, $80 million

The Tigers gave Jack Flaherty a two-year, $35 million deal after an inconsistent season, but he didn't have the same track record as a frontline starter. The four-year, $80 million deal that Eduardo Rodríguez signed with the D-backs feels closer to the market Peralta can expect this winter, with an outside shot at a fifth year.

Age: 27 Stats: 76 G, 28 HLD, 2.83 ERA, 1.08 WHIP, 11.2 K/9, 86.0 IP WAR: 1.9

One of the youngest players in the 2026-27 free agent class, Adrian Morejón fits prominently into the conversation of the most dominant left-handed relievers in baseball.

Over the past three seasons, he has posted a 2.58 ERA, 1.09 WHIP and 10.0 K/9 with 60 holds in 211 appearances. His 86.0 innings and 11.2 K/9 in 2026 were both career-high marks. His 107 strikeouts ranked third among all relievers.

Predicted Contract: 5 years, $90 million

The Dodgers gave Tanner Scott a four-year, $72 million deal for a dominant late-inning lefty with swing-and-miss stuff. He was two years older when he hit the open market. A matching AAV and a fifth year seem reasonable for Morejón.

Age: 31 Stats: 670 PA, 148 OPS+, .281/.381/.484, 62 XBH (26 HR), 26 SB WAR: 5.7

Durability and consistency should help Randy Arozarena earn a nine-figure payday, as he has averaged 152 games over the past six seasons while recording at least 20 home runs and 20 steals every year during that span.

His 148 OPS+ in 2026 was a career high and ranked fourth among qualified AL hitters. His .381 on-base percentage was good for fifth on the AL leaderboard. His stellar postseason track record further adds to his appeal for contenders looking for the missing piece offensively.

Predicted Contract: 5 years, $115 million

Nick Castellanos was coming off a career year offensively and was one of the top bats on the market when he signed a five-year, $100 million deal with the Phillies. Arozarena should be able to surpass that contract, despite the fact that he is two years older than Castellanos was when he signed.

Age: 27 Stats: 614 PA, .306/.383/.609, 82 XBH (39 HR), 8 SB

Teruaki Sato won the NPB Triple Crown with the Hanshin Tigers in 2026, hitting .306/39/106. That came on the heels of a 40-homer, 102-RBI campaign the previous year.

With 164 strikeouts and a 26.7 percent strikeout rate, he possesses some of the same swing-and-miss concerns that ultimately limited Munetaka Murakami's market last winter. However, given Murakami's success and Sato's more valuable defensive profile, his earning power might not face the same limitations.

Predicted Contract: 6 years, $120 million

The six-year, $113 million deal that Jung Hoo Lee signed with the Giants looks like a logical starting point for Sato's market. While he is two years older than Lee was when he made the move stateside, the glaring lack of impact bats available this winter should give him a nice boost.

Age: 31 Stats: 32 GS, 12-10, 3.21 ERA, 1.18 WHIP, 159 K, 185.0 IP WAR: 4.3

Michael King rejoined the Padres last offseason on a three-year, $75 million deal, despite injuries that limited him to just 73.1 innings in 2025. The back-loaded deal included opt-outs after 2026 and 2027. He would be leaving $58 million on the table if he exercises that opt-out.

After a fully healthy season, punctuated by a fantastic postseason (3 G, 2 GS, 1-0, 1 SV, 0.64 ERA, 15 K, 14.0 IP), opting out should be a no-brainer. He would immediately slot in ahead of Trevor Rogers and Freddy Peralta as the No. 2 pitcher on the market.

Predicted Contract: 5 years, $120 million

Robbie Ray signed a five-year, $115 million deal following his Cy Young season in 2021. His earning power was somewhat limited by an inconsistent track record. With only two full seasons as a starter under his belt and injury issues in 2025, King has a comparable free agency outlook.

Age: 29 Stats: 26 GS, 12-7, 2.72 ERA, 0.96 WHIP, 186 K, 158.2 IP WAR: 4.6

One of the best starting pitchers to ever hit the free agent market while still being very much in the prime of his career, Tarik Skubal will have his sights on a record-setting contract.

He didn't miss a beat after joining the Dodgers at the deadline, going 5-2 with a 2.61 ERA, 1.05 WHIP and 70 strikeouts in 62 innings. He threw the ball well in a pair of postseason starts.

Predicted Contract: 9 years, $360 million

The nine-year, $324 million deal Gerrit Cole signed with the Yankees at the same age will be the mark Skubal aims to surpass. A $40 million AAV is within reach for the clear headliner of the 2026-27 free-agent class.