The Pirates’ 10 Greatest Pitchers

Babe Adams (1907, 1909-16, 1918-26)

The right-hander from Indiana, one of the toughest to reach base against in his time, essentially lived two careers with the Pirates: An early tenure highlighted by a marvelous rookie performance in the World Series, and a later renaissance after he had all but lost his way in the mid-1910s.

After a failed (6.95 ERA) audition in 1907, Adams returned to the Pirates in 1909 as a much better pitcher—but seldom used, with 12 starts among 25 appearances. Still, he finished the year at 12-3 with a wowing 1.11 earned run average, and manager Fred Clarke didn’t forget those numbers when he decided to live or die on the mound with Adams for that year’s World Series against the high-powered Detroit Tigers. Adams didn’t let Clarke down; he went the distance in all three of his starts and won them all (including the Game Seven decider) to become the first three-game winner in a seven-game series—allowing just four earned runs in 27 innings while holding the great Ty Cobb to a mere single in 11 at-bats.

The success of the 1909 Series catapulted Adams to ace status, using a fastball-curve combination and superior control that led to few walks and much success, including 20-win campaigns in 1911 and 1913. He set a major league mark in 1914 when he pitched 21 innings in one game without allowing a single walk; it’s theorized that the overuse of his arm that day may have contributed to his decline that bottomed out a few years later when he won just two of 11 decisions with a wretched 5.72 ERA that was inexcusable for deadball times. At age 34, he appeared finished.

Adams spent the next two years in the minors trying to work his way back, and the Pirates were impressed enough that they brought him back late in the 1918 season, giving vintage performances in three starts. Over the next three seasons, it could have been argued that Adams was better than before; he led the NL each year in on-base percentage allowed, leading the circuit in 1920 with eight shutouts while issuing just 18 walks—the fewest ever allowed by a pitcher throwing 250 or more innings. (For his career, Adams walked 1.3 batters per nine innings, second best in modern major league history after early teammate Deacon Phillippe.)

After turning 40, Adams began to regress once more, but played on through 1926 and becoming the only Pirate to play for both the 1909 and 1925 champion teams, though he pitched just one scoreless inning in the 1925 Series against Washington. A year later, Adams was unceremoniously dumped when he was a benign instigator and the “A” in the “ABC Affair,” named after three veteran Pirates players (Adams, Carson Bigbee and Max Carey) who revolted against former manager and then-bench coach Fred Clarke, alleging that he had caused tremendous and unnecessary friction with players and manager Bill McKechnie. With the other two mutineers, Adams was released and, at age 44, never played again.

Bob Friend (1951-66)

One of the more luckless star pitchers to take the mound, Friend became the only pitcher in big league history to lose 200-plus games without winning 200—through no fault of his own.

Appropriately nicknamed Warrior, Friend was one of many Pirates stars from the 1960s who was forced to grow up fast in the 1950s on some terrible, inexperienced teams at Forbes Field. In each of Friend’s first seven years at Pittsburgh, the Pirates finished with sub-.500 records; he unfortunately towed the losing line with a 28-50 mark and 4.62 ERA over his first four campaigns, but suddenly matured in 1955 when he became the first pitcher in major league history to win an ERA crown (2.83) for a last-place team. His 14-9 record that year was in sharp contrast to the Bucs’ 60-94 standing.

In response to his stellar 1955 showing, the Pirates made Friend the staff workhorse; he inherited the role well. He averaged 16 wins over the next eight years, co-leading the majors with Warren Spahn in 1958 with 22 victories—but also led the NL in losses with 19 each in 1959 and 1961, part of a broader problem that would plague Friend throughout his career, even after the Pirates developed good hitting: Lack of run support. This was best exemplified in 1963 when he sported a career-best 2.34 ERA—but finished at 17-16, losing six games when his team failed to score a single run. In fact, only five other pitchers have suffered more career shutout losses than Friend.

Friend couldn’t rise to the occasion in the 1960 World Series, getting hammered in three appearances (losing twice) against the New York Yankees before the Pirates survived and won in seven games.

The all-time Pirates leader in innings pitched, strikeouts and games started, Friend is also known among trivia buffs as the pitcher who surrendered the first of Pete Rose’s 4,256 hits in 1963.

Wilbur Cooper (1912-24)

A fast-working thrower who had a graceful, almost effortless pitching motion, Cooper was an A-list hurler for the Pirates from start to finish, doing his best to keep an otherwise dreadful Pittsburgh team respectable during the hard times of the 1910s—then enjoying the fruits of his labor from a rejuvenated roster in the 1920s.

Cooper had a fantastic first taste of the majors in 1912—starting four games and finishing three of them, with two shutouts, a 3-0 record and a 1.66 ERA. In 1916 he produced a career-best 1.87 ERA but could only manage a 12-11 record as the Pirates failed to score in seven of his losses; a year later, he took home a 17-11 mark for a Pittsburgh team that finished last in the NL at 51-103.

An improved, muscled-up Pirates roster into the 1920s began to improve the won-loss figures for the team—and certainly for Cooper, by now the established workhorse. He won 19 games each in 1918 and 1919—two years in which the schedule was shortened from the effects of the Great War—then hit the 20-win barrier in 1920 with a 24-15 record; he would collect at least 20 victories over three of the next four years. But Cooper’s rambunctious behavior didn’t sit well with religious Pirates manager Bill McKechnie, and he was sent to the Chicago White Sox in 1924—missing out on the Pirates’ championship season of 1925. Cooper quickly deteriorated in Chicago and was out of baseball within two years, but left Pittsburgh—then as now—as the team’s all-time leader in wins with 202.

Deacon Phillippe (1900-11)

Humble but stern in appearance, Phillippe was part of the mass migration from Louisville to Pittsburgh after the Colonels folded in 1899 and made an immediate impact for the Pirates—winning at least 20 games in each of his first four years with the Bucs, part of an impressive career resume in which he never had a losing record, finishing with a lifetime 189-109 mark.

Phillippe is best known as the winner of the very first World Series game in 1903, defeating the Boston Americans (now Red Sox) 7-3. The Pirates, who went on to lose the series five games to three, were only able to make it look respectable because of Phillippe, who essentially became a one-man rotation by starting five games in a 13-day stretch—going the distance in all of them—and being the pitcher of record in all three Pirates wins. In 1909, the Pirates returned to the World Series and Phillippe, used more sparingly, was there—as the 37-year-old right-hander tossed six shutout innings over two relief appearances. Phillippe performed full-time for the last time in 1910, winning his last 13 decisions as part of a 14-2 record; but a combination of injuries and advancing age became too much for him to continue.

Since the pitching mound was moved to its current 60’6” distance from home plate in 1893, no pitcher has a lower rate of allowing walks than Phillippe, with 1.25 per nine innings.

Ray Kremer (1924-33)

The Oakland native slowly emerged as a Pacific Coast League ace through his 20s, and that was enough for the Pirates to bring him in as a 31-year-old rookie in 1924; he wouldn’t disappoint in his new home out east, producing an exemplary 74-32 record over his first four years on his way to a career major league mark of 143-85.

A known prankster who kept his teammates on their toes, Kremer kept opposing hitters in knots with an unusual habit of changing up his deliveries from overhand to underhand in the course of a game. He won ERA crowns in back-to-back seasons (1926-27) and twice won 20 games—the latter of those two achievements taking place in 1930, when he became the symbol of that year’s hitting madness with the highest ERA (5.02) ever recorded by a 20-game winner in the NL.

Kremer was a pitching hero for the Pirates during the Bucs’ seven-game triumph over the Washington Senators in 1925, winning two games—one in a critical Game Seven relief appearance.

Sam Leever (1898-1910)

Leever was one of many mainstays (along with Honus Wagner, Fred Clarke, Phillippe, et al) on the constantly winning Pirates teams of the 1900s, and no one profited more from it—leading the NL three times in winning percentage and, from 1901-09, producing a terrific 151-59 record.

Nicknamed the Goshen Schoolmaster for his serious attitude (and his Ohio hometown), Leever toiled hard in his first full year with the Bucs in 1899, leading major league pitchers with 51 appearances and 379 innings but also finishing with an unjust 21-23 record that would be the only losing mark of his 13-year career. Leever never played the workhorse again, as his time on the mound moderated—but not his efficiency.

Leever would top 20 wins thrice more, including a fantastic 1903 campaign in which he co-led the team (with Phillippe) with 25 wins against seven losses and led the NL with a 2.06 ERA and seven shutouts—two of which came during a June run in which the Bucs won six straight games by shutout. But his year ended on a disappointing note; his arm became sore at season’s end after an extensive fit of weekend trapshooting, and he was ineffective in the inaugural World Series against Boston.

Vern Law (1950-51, 1954-67)

Like Bob Friend, Law was a Pirates lifer who saw the best and worst of times in the Steel City—but unlike Friend, survived with a winning career record.

Along with many of his teammates who grew into champions by 1960, Law—a Mormon given the nickname Deacon for his calm demeanor and refusal to get aggressive with inside pitches—struggled early in his career; missing two years to military service only quelled his progress. He made news on July 19, 1955, when he toiled for 18 innings against the star-studded Milwaukee Braves; no pitcher since has thrown so deep into a game. (Law threw 10 innings in his next start, and it took him three weeks for his arm to return to full strength.)

Law turned the corner in 1957 with a 10-8 record and, more importantly, a sharp 2.87 ERA. Three years later, Law peaked along with the Pirates—earning the Cy Young Award with a 20-9 record, 3.08 ERA, a win in the All-Star Game and two more in the Bucs’ thrilling seven-game World Series victory over the Yankees.

A string of injuries, starting with a torn rotator cuff in 1961, cut into Law’s pitching abilities through the remainder of his career—with the exception of a 1965 campaign in which he finished 17-9 with a career-low 2.15 ERA, earning him Comeback Player of the Year honors.

Vic Willis (1906-09)

After toiling with a derelict Boston franchise in the NL and constantly struggling to earn a winning record despite his excellence on the mound, Willis went through the ultimate reversal of fortune by being dealt to the Pirates in 1906, quickly catching up with and surpassing the .500 mark for his career with a quartet of outstanding years.

In Boston, Willis was a proven, tireless workhorse badly underpaid by management and badly unsupported by teammates, the latter largely responsible for his leading the NL in losses in each of his final two years—including a modern-record 29 in 1905—before being dealt to the Bucs. In Pittsburgh, the Pirates gave Willis respect both in the wallet and at the plate, giving him substantially more offense to work with. The won-loss totals were a mirror-image from his days in Boston; in four years with the Pirates, Willis was 23-13, 21-11, 23-11 and 22-11. Also helping was Willis himself, producing a 2.08 ERA through his short tenure in the Steel City.

In his final year at Pittsburgh, Willis finally got his first taste of the postseason by appearing in two games—one as a starter—against Detroit in the World Series, but his performance was uninspiring. By then he had long since warn out his welcome with the Pirates and especially manager Fred Clarke, who released him after the year; sold to St. Louis, Willis showed major signs of rust and soon after retired.

Over eight decades later, Willis was recognized for the fact that because he had futilely labored for so long in Boston, he was denied a real chance at 300 career wins—and was thus voted into the Hall of Fame.

Rip Sewell (1938-49)

A late bloomer whose early career stalled within the Detroit organization (a spring training fight with star hitter Hank Greenberg didn’t help), Sewell’s development accelerated in Pittsburgh by the time he reached his mid-30s with one of the most fascinating pitches ever seen.

Sewell accidentally had his right toe shot at in a hunting accident on the day Pearl Harbor was attacked; because of his newfound handicap, Sewell not only couldn’t enlist in the military, his baseball career was jeopardized as well. That next spring, teammate Maurice Van Robay suggested using an “eephus” pitch, a looping delivery that arced as high as 25 feet to the heart of the plate. It worked; Sewell became a wartime star for the Pirates, ultimately winning 21 games in successive seasons (1943-44). Hitters had a tough time sizing up the eephus as it came down into the strike zone at an unusually exaggerated angle; umpires were just as frustrated and, at first, refused to call the pitch a strike. It took a demo session in which Sewell showed off the trajectorial physics of the eephus to better understand it.

Sewell and his eephus both languished when the vets returned from World War II but he was named to the 1946 All-Star Game anyway—where Ted Williams became the one and only batter to knock an eephus out of the park. In response, Sewell smiled off the moment, bragging that he told Williams what was coming.

Jesse Tannehill (1897-1902)

A small (5’8”, 150 pounds) but multi-talented player, Tannehill debuted in 1897 with a Pirates team that wasn’t sure whether to use him as a pitcher or outfielder; they let him do both at first, playing 33 games in the field with a .266 average while winning nine games in short duty on the mound. But gradually the Bucs realized that his ultimate calling was for the mound—and for the next five years, he would win 20 games four times, taking the NL ERA crown with a 2.18 mark in the one year (1901) he didn’t reach 20, finishing at 18-10.

Like most Pirates pitchers of the time, wins seemed almost too easy to come by for Tannehill, who was 58-22 over the first three years of the 1900s. His final year at Pittsburgh—in which he finished 20-6 with a career-low 1.95 ERA—came to a premature end when he led a coalition of teammates who wanted to jump to the American League during its infant, confrontational years with the NL. The Pirates released him, and he wound up playing the next seven seasons in the junior circuit, principally for the Boston Americans (Red Sox), where he would win over 20 games two more times.