Pittsburgh Pirates' Paul Skenes: Honors without a Ring

The Pittsburgh Pirates’ ace pitcher Paul Skenes has had a tremendous start to his Major League Baseball career. In his first two seasons he has won several of the major awards presented following the end of each baseball season. Unfortunately for the young man is the team he plays for. Perennial losers and a club that hasn’t made the playoffs since 2015, the Bucs future is bleak.

The Pirates chances of competing for a postseason appearance is next to none. What does that mean for one of the best pitchers in baseball? Paul Skenes may never have a shot at winning a World Series title if he remains in Pittsburgh.

Having won the Rookie of the Year and the Cy Young Award in back-to-back years, places Skenes in a very special Pirates class. Only two men before him wearing a Pittsburgh Pirates uniform have won the Cy Young Award. They were Doug Drabek in 1990 and Vern Law in 1960 when the Bucs upset the New York Yankees to win the World Series.

As for his first season in the majors, Skenes won the Rookie of the Year Award, now known as the “Jackie Robinson Award,” only Jason Bay before him became the first Pirates player to win the honor. With the Cy Young Award first being presented in 1956 and the rookie honors beginning with Jackie Robinson in 1947, only five players from Pittsburgh have won both awards.

The irony in this is only Vern Law played for a championship team. For Doug Drabek, he and the Bucs made the playoffs in three straight seasons from 1990 to 1992 only to lose all three series. In 1990 it was the Cincinnati Reds knocking Pittsburgh out of the World Series race four games to two. The next season the Atlanta Braves ousted the Pirates four games to three and did it again in 1992.

In that last series, former Pirates’ player Sid Bream who was playing for the Braves at the time raced home with the winning run in game seven beating a solid throw from Barry Bonds. That would be Pittsburgh’s last playoff appearance until Andrew McCutchen and gang made it back in 2013. 20 years without a playoff appearance and now Paul Skenes is part of a team that hasn’t sniffed a post season spot since 2015, 10 years ago.

The question for Paul Skenes now is whether he will be willing to spend his entire career with the Pirates and most likely never get to a playoff game let alone make it to the World Series? The current state of the Pittsburgh Pirates has them nowhere near contending for even a division title shot. Can Skenes live with that?

The one thing that stands out for me with the 1992 championship series starring Doug Drabek is that in that winner take all game, he worked into the ninth inning and Sid Bream had gotten on base with Francisco Cabrera at the place and it was my opinion then and still is now that Pirates manager Jim Leyland should have left Drabek in the game and see if he could get the Pirates another chance on offense with the game tied 2-2.

Instead, Stan Belinda was brought in to relieve Drabek and with Cabrera's base hit, Bream raced home with the winning run. For Doug Drabek, 1992 was also his final season as a Pirate and the following season he was in Houston playing for the Astros where he would spend the next four seasons leading the league in 1992 for losses with 18. He would never again see a playoff game. Unfortunately, Drabek also lost three of the four games in that 1992 series.

Vern Law’s career mirrored Drabek’s with the exception that he played his entire career in Pittsburgh. In that 1960 season he won 20 games, losing only nine games and even hit a home run while at the plate. However, unlike Drabek he did become a world champion pitcher. But, in a 16-year career, Vern Law made it to the World Series just once.

As for the Rookie of the Year Award, being it has only been Skenes and Bay, for Jason Bay he played six respectable seasons in Pittsburgh then moved on to the Boston Red Sox where he played in three post season series as Boston defeated the Los Angeles Angels in 2008 in the divisional round but then lost in two straight seasons in first the championship series to the Tampa Bay Rays and the following season again in the divisional round to the Angels.

So, the bottom line for Skenes is playoffs or no playoffs? If he remains a Pirate as he seems to be indicating for the moment or plays out his contract and moves on, that might be his only chance at becoming a championship pitcher. He was a champion in the 2023 College World Series with Louisiana State University and there have been scattered rumors about the Pirates trading Skenes away but Pittsburgh management scoffs at that prospect. Maybe it is because they’ve let so many star players leave town in the past (Barry Bonds, Gerritt Cole, etc.).