5 Greatest Pittsburgh Pirates Pitchers of All Time

Few lists are tougher to put together than that of the Pittsburgh Pirates’ top five pitchers in history. The list is loaded with similar pitchers with similar totals from similar eras.

Most of the top 10 pitchers in WAR in Pirates history played at least part of their career in the dead-ball era. Many others played before the Vietnam War.

As such, you won’t find many names you’re too familiar with on here, unless, of course, you’re a Pirates die-hard or a baseball historian. We included just one pitcher who has played for the Pirates since 1965. 

A shoutout to John Candeleria, Deacon Phillippe, Ray Kremer and Vern Law, who all earned consideration for this list, coming up just short. If you want to include them in yours, feel free.

Here are our five greatest Pirates pitchers of all-time, and don't miss our list of five greatest Pirates hitters when you're done.

5. Paul Skenes (2024-Present)

Yes, Skenes has played only two-plus seasons of Major League Baseball at the time of this writing. But he’s been so good in those two-plus seasons that he deserves this spot, even if the numbers don’t eclipse some we left off.

Skenes stepped into the Majors fully formed, practically. He won National League Rookie of the Year in 2024 while earning third in Cy Young Award voting after going 11-3 with a 1.96 earned-run average, a .0947 WHIP with 170 strikeouts over 130 innings.

The next year, with 11 more starts, he picked up where he left off, leading all of baseball with a 1.97 ERA and a .0948 WHIP with 216 strikeouts over 187 2/3 innings, winning the Cy Young.

As long as injuries don’t creep up, it’s hard to imagine Skenes not remaining one of the best in the sport for the next decade.

4. Sam Leever (1898-1910)

Leever teamed with Phillippe in the early 1900s to give the Pirates a solid one-two punch in the rotation. He helped the team win the 1909 World Series in his second-to-last season in the majors, though at that point, he had become a reliever.

Leever joined the club in 1898 and would ultimately go 194-100 over his 13-year Pirates career, leading the NL in winning percentage three times. He also led the league once in shutouts, ERA, and innings pitched.

For his career, Leever ranks fourth in club history in pitching WAR and ERA and is tied for second in wins.

3. Bob Friend (1951-1965)