Pirates linked to two expensive free agent lefties, but only one of them fits in Pittsburgh

The Pittsburgh Pirates have an obvious hole in their starting rotation, and former MLB general manager Jim Bowden has identified two expensive potential solutions. Unfortunately, only one looks like a particularly smart investment.

In his recent ranking of the top 40 free agents for 2026-27 in The Athletic, Bowden listed Pittsburgh among the best fits for left-handed starters Robbie Ray and Foster Griffin. He projected a two-year, $45 million contract for Ray and a three-year, $67 million deal for Griffin.

Neither would come cheap. But for a Pirates team trying to build on its first winning season since 2018, the distinction between the two goes well beyond their projected price tags.

Pittsburgh's projected rotation of Paul Skenes, Jared Jones, Bubba Chandler, Braxton Ashcraft and Mitch Keller is entirely right-handed. Adding a reliable left-handed starter would provide some much-needed balance, not to mention insurance against the injuries that complicated the club's pitching plans in 2026.

Still, that doesn't mean the Pirates should spend $45 million on just any left-handed starter.

Robbie Ray would be an expensive gamble for the Pirates

Ray certainly has the résumé to attract Pittsburgh's attention. The 2021 American League Cy Young Award winner posted a 3.59 ERA over 182 1/3 innings for the San Francisco Giants in 2025, his first full season following Tommy John surgery.

He followed that with a 3.08 ERA in 122 2/3 innings for San Francisco in 2026 before being traded to the San Diego Padres at the deadline. Ray struggled following the trade, however, recording a 5.02 ERA across nine starts before delivering another disappointing performance in the postseason.

At 35 years old, Ray is no longer the dominant pitcher who earned a five-year, $115 million contract following his Cy Young campaign. He's still a capable mid-rotation starter, but paying him $22.5 million annually through his age-36 and age-37 seasons would be a substantial gamble.

And Pittsburgh is already carrying significant financial obligations to Keller, who is owed $38.8 million over the next two seasons following an injury-shortened 2026 campaign. Committing another $45 million to an aging starter with a significant injury history would leave the Pirates with considerable money tied up in two pitchers whose best days could be behind them.

That's hardly an ideal situation for an organization that still needs to address several offensive weaknesses.

Foster Griffin offers Pirates a more sensible long-term investment

Griffin isn't exactly a bargain, either. Bowden's projected three-year, $67 million contract would represent an even larger total commitment than Ray's. But at 31 years old, Griffin is a younger pitcher with a potentially longer window of effectiveness.

After spending three seasons pitching in Japan, Griffin returned to the majors in 2026 on a one-year, $5.5 million contract with the Washington Nationals. He rewarded Washington with a 12-3 record and 3.06 ERA across 22 starts before being traded to the Cleveland Guardians.

Like Ray, Griffin struggled following his deadline move, posting a 5.19 ERA with Cleveland. However, his 3.54 FIP suggested he pitched better than his results indicated, and he recovered to deliver a strong postseason performance.

There are legitimate concerns about committing three years and $67 million to a pitcher with just one full MLB season as a starter since returning from Japan. His struggles in Cleveland shouldn't be dismissed, either.

Still, his projected average annual salary of approximately $22.3 million is actually slightly lower than Ray's, despite Griffin being four years younger. If the Pirates are going to make that kind of investment, Griffin offers the more appealing long-term fit.

Of course, there's another question hanging over both possibilities: Would Pittsburgh actually spend more than $20 million annually on a free-agent starting pitcher? The Pirates have other expensive decisions looming, including whether to retain Brandon Lowe, and they can't afford to devote their limited financial flexibility to another questionable veteran investment.

Griffin wouldn't be a risk-free signing, but he would address an immediate need while offering a better chance of contributing beyond the next season or two. Ray might be the more recognizable name, but that doesn't make him the better choice.

For a team that finally has reason to believe its competitive window is opening, the priority should be finding players who can help keep it open — not paying a premium for what they accomplished five years ago (see: Marcell Ozuna).

Add us as a preferred source on Google

Follow