Cy Young award winners from the Pirates

In mid-November 2025, the Cy Young award winners were announced. In the AL, Tarik Skubal won the award again. He finished the season with a 2.21 ERA and a 0.89 WHIP over 195.1 innings, while striking out 241 batters. Skubal became the 12th pitcher to win back-to-back Cy Young awards. In the NL, the award goes to Paul Skenes. Skenes owned a 1.97 ERA and a 0.95 WHIP over 187.2 innings. In the 2025 season, Skenes struck out 216 batters.

 

Paul Skenes won the award unanimously with all 30 first-place votes. While watching his highlights and interviews, I’m just wondering which pitchers from the Pirates did win the Cy Young award previously. To solve my doubt, I decided to check on the great baseball reference website.

 

The first Cy Young award winner from the Pirates was Vern Law. He won the Cy Young award in 1960. Back then, he made 35 starts for the Pirates, posting a 3.08 ERA and a 1.13 WHIP over 271.2 innings. He got 20 wins and took 9 losses. Additionally, he got 2 wins in the 1960 World Series and helped the Pirates win the title. However, in 1961, he only made 10 starts and 1 relief appearance for the Pirates, posting a 4.70 ERA and a 1.52 WHIP over 59.1 innings.

 

The second Cy Young award winner from the Pirates was Doug Drabek. Drabek won the NL Cy Young award in 1990. Back in 1990, he made 33 starts for the Pirates, posting a 2.76 ERA and a 1.06 WHIP over 231.1 innings. He earned 22 wins and got 6 losses. He made 2 starts in the 1990 postseason, giving up 4 runs (3 earned) in 16.1 innings. The Pirates fell short in the NLCS. In 1991, Drabek made 35 starts for the Pirates. He owned a 3.07 ERA and a 1.31 WHIP over 234.2 innings. In 1991, he got 15 wins and took 14 losses.

 

Paul Skenes is the third pitcher from the Pirates to win the Cy Young award. After making it into the big leagues in 2024, his performance has been quite consistent. In 2024, he made 23 starts, posting a 1.96 ERA and a 0.95 WHIP over 133 innings. Skenes had 11 wins and lost 3 times in 2024. This season, he earned 10 wins and took 10 losses.

 

When we look at these 3 Cy Young award winners from the Pirates, Law and Drabek each earned at least 20 wins in the season when they won the Cy Young award, however, Skenes only got 10 wins. Meanwhile, Law helped the Pirates win the 1960 World Series title. Drabek did pitch for the Pirates in the postseason in 1990. Nonetheless, we still don’t know when Paul Skenes will make his postseason debut. Moreover, a season after winning the Cy Young award, Law and Drabek didn’t pitch as well as they did. Hence, it will be worth watching Paul Skenes’ performance in the 2026 season. In particular, he will pitch for the team USA in the World Baseball Classic. Will this become the x-factor in the next season?