Pirates Signing Former Cy Young Winner Comes With Less Risk Than Realized

The Pittsburgh Pirates have to enter this offseason with a wide range of options on the table. For one, the Pirates have to feel like if they make the necessary moves on both sides of the baseball, they can find themselves in a position to make the playoffs. 

The Pirates, at least on paper, seem to be a decent, young, and talented team, though a lot of it again is going to come down to what the front office decides to do this winter. 

I don't think the Pirates are necessarily in a bad spot to improve on both sides of the baseball this winter, but I always have my fair share of questions because of the lack of spending that the front office has shown us for most of this organization's existence. 

The harsh reality is that until the Pirates show us anything differently, it's going to be tough to trust them. At the same time, the Pirates find themselves in a position where they can find some decent and cheap talent. 

Not to say that guys are going to be a couple of million dollars, but if they can find a way to land a starter who's about $20 million per year who can come in and get outs at a high level, I think it's something they should consider. 

The Athletic recently suggested just that with Robbie Ray, a left-hander who has been one of the more difficult players in baseball to evaluate over the past couple of years.

“Ray had a 3.59 ERA in 182 1/3 innings for the Giants in 2025, his first full season back after 2023 Tommy John surgery. He followed that up this year by posting a 3.08 ERA in 122 2/3 innings for the Giants before being traded to the Padres at the deadline. Ray didn’t pitch as well after the deal, posting a 5.02 ERA in nine starts, and he was ineffective in the postseason. 

“He isn’t the Cy Young Award-level starter that he was when he was last a free agent following the 2021 season, but he’s still a solid mid-rotation starter… Best team fits: San Diego Padres, Pittsburgh Pirates, Chicago White Sox… Contract prediction: 2 years, $45 million,” Jim Bowden of The Athletic wrote.

My reasoning for Ray being tough to evaluate is all because of the injuries he's dealt with. 

There have been times when Ray has managed to stay healthy and he looks really good, but he also threw just 30.2 innings in 2024 and 3.1 innings in 2023. On defense, he's coming off two years in a row in which he threw more than 165 innings each campaign, for 348 over those two years. 

His numbers have also been really good throughout that span, posting a 3.62 ERA and striking out 326 hitters. 

However, if the Pirates think they're going to get the Ray of 2021, when he won the Cy Young Award with the Toronto Blue Jays, they're going to be sadly mistaken.