Tarik Skubal enters the 2027 MLB free agency class as the clear headline act, with expectations that the two-time Cy Young Award winner will secure the most lucrative contract ever awarded to a pitcher. As teams prepare for a likely December 1 lockout, the market for top-tier talent is moving on an accelerated timeline.
The Skubal Market
Skubal, who is entering his age-30 season, is coming off a 2026 campaign where he recorded 5.2 WAR. Despite arthroscopic elbow surgery sidelining him for a month, which prevented him from winning a third consecutive Cy Young Award, he remains the most coveted player available. His track record of 21.3 fWAR and a 2.42 FIP since 2023 solidifies his status. While he once hoped to spend his entire career with the Detroit Tigers, that prospect has shifted. Teams seeking an ace are expected to center their plans on him, though clubs must weigh his talent and age against health considerations regarding his recent surgery.
The Chicago Cubs have the financial capacity to pursue Tarik Skubal as they look to address a need for starting pitching. With a massive free-agent class of their own—including Shota Imanaga, Kevin Gausman, Matthew Boyd, Clay Holmes, and David Peterson—the club is projected to see its luxury tax payroll decrease by roughly $90 million for 2027. This financial flexibility leaves Jed Hoyer and his front office with room to operate, potentially making Skubal a primary target to address a starting rotation that ranked among the bottom third of playoff-bound teams last season.
Evaluating the Pitching Class
The 2026 free-agent pitching class offers a range of upside, experience, and risk. Sonny Gray, a 37-year-old coming off a season where he led MLB with 18 wins and recorded a 2.72 ERA for the Red Sox, is a notable option. However, evaluators note that his FIP and strikeout rate raise questions about the long-term sustainability of his performance. Freddy Peralta is another arm in the mix; after an early-season collapse, he rebounded with a 3.25 ERA across 10 regular-season starts for Tampa Bay and a 2.95 ERA over 21⅓ playoff innings.
Michael King also enters the market following a three-year stretch where he maintained a 3.15 ERA and 131 ERA+, including 185 innings pitched last season. The market also features Adrian Morejon, who at 28 is coming off a career-best season with a 2.83 ERA and a 30.4% strikeout rate across 86 innings. Teams are also monitoring Kaima Taira, though there is internal debate regarding whether he is best suited for a starting role or a bullpen assignment.
Cubs Face Offseason Roster Losses as Free Agency Opens
The Chicago Cubs face a busy offseason beyond their pitching needs, as players like Seiya Suzuki, Tyrone Taylor, and Ian Happ have hit the open market. The departure of these contributors necessitates significant work for the front office. Elsewhere, teams are looking at players like Jazz Chisholm Jr., a 29-year-old power-speed threat who has averaged 24 homers and 37 stolen bases over the last three seasons. While Chisholm’s defensive metrics remain a point of contention—with Statcast’s Outs Above Average favoring him while DRS ranks him poorly—his prime age makes him a compelling option.
Brandon Lowe also provides a unique profile, coming off a 2026 season where he recorded a career-high 4.9 fWAR. As teams rush to beat the December 1 deadline, the focus remains on balancing current performance against future durability, with contenders looking for ways to distinguish lasting skill from hot streaks.
Earlier coverage: Tarik Skubal enters 2026 MLB free agency market
