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As the General Managers' Meetings concluded at the ARIA Resort and Casino in Las Vegas, Pittsburgh Pirates general manager Ben Cherington and his front office counterparts from across Major League Baseball began laying the groundwork for what could be a busy offseason. With a lockout looming on December 1, teams are eager to make moves, and one report from the meetings indicated that the Pirates are in the market for left-handed pitching to bring balance to their staff.
One free-agent southpaw who fits that description is starter Robbie Ray. The 35-year-old could offer Pittsburgh a different look in 2027, especially given the team's need for a left-handed starter. Ray has been among the more reliable pitchers in baseball since his debut in 2014, logging seven seasons with an ERA under 4.00, including each of the past two years, and has consistently been a 30-plus start workhorse.
A two-time All-Star in 2017 and 2025, Ray also captured the American League Cy Young Award in 2021 with the Toronto Blue Jays after leading the AL with a 2.84 ERA and topping the majors with 248 strikeouts. Over the 2025 and 2026 seasons, he compiled a 24-16 record in 62 starts, posting a 3.62 ERA across 348.0 innings with a 1.28 WHIP and 8.4 strikeouts per nine innings. Remarkably, he achieved this after returning from Tommy John surgery, which limited him to just eight combined starts in 2023 and 2024.
Ray has also been stingy with home runs throughout his career, and his 44 home runs allowed over the past two seasons ranked as the 20th-fewest among qualified pitchers. PNC Park, known as a pitcher-friendly venue, could further benefit him in 2027. Additionally, Ray made significant strides with his off-speed offerings, as his changeup and curveball went from run values of -1 and -8, respectively, in 2025 to +5 and +7 in 2026, according to Statcast.
The Pirates' entire 2026 starting rotation was right-handed, featuring Paul Skenes, Braxton Ashcraft, Jared Jones, Mitch Keller, and Bubba Chandler, with Carmen Mlodzinski also making starts in the first two months. Pittsburgh has previously employed a free-agent left-handed starter, most recently Andrew Heaney in 2025, and Ray could fill a similar role while adding versatility to the staff.
Key Analysis
While Ray addresses many of the Pirates' needs, there are valid concerns. He struggled after being traded from the San Francisco Giants to the San Diego Padres at the deadline, recording a 5.02 ERA over nine starts and 43 innings, averaging fewer than five innings per outing with 33 strikeouts and 27 walks. At 35, Ray has also seen a decline in velocity, with his four-seam fastball dropping from 94.8 mph to 93.1 mph and his sinker from 88.6 mph to 86.1 mph between 2021 and 2026.
Any potential deal would likely need to be short-term, perhaps one or two years, with an average annual value in the $10-$15 million range making the most sense for Pittsburgh if the club is willing to increase payroll. The question is where Ray would fit in a rotation that is already full, unless the Pirates opt for a six-man rotation. Still, starting pitching depth is always a commodity, and Ray would also satisfy the team's desire for more left-handed pitching overall. It would not be surprising to see Pittsburgh pursue Ray, and there is a real chance he could don black and gold next season.