The 20 Greatest Pittsburgh Pirates of All-Time

Welcome to the eighth installment in our “Top 20” series which looks at the twenty top players for each franchise based on Wins Above Replacement.

This series isn’t really about the twenty rankings, it’s just a way to talk about these players.

20. Vern Law

Law is one of only three pitchers born in Idaho who won as many as 100 games. The others are Larry Jackson and Jason Schmidt. In the 1960 World Series, Law started Games One, Four, and Seven for the Pirates, and he defeated the Yankees twice.

After the Pirates clinched the 1960 pennant, Law injured his ankle during the celebration. He changed his delivery and ended up harming his back and shoulder. As a result, he spent several seasons trying to get back to form.

19. John Candelaria

Tall and leggy, Candelaria was an excellent basketball player in Puerto Rico, but he made the decision to switch to baseball. Many people thought he was crazy, but a year later the Pirates drafted the 6’7 left-hander in the second round. He was in the Pittsburgh rotation in 1975, no-hit the Dodgers in 1976, and won twenty games and the ERA title the following season.

18. Dave Parker

There are players in every generation who have Hall of Fame talent, who are just as gifted as the superstars of that era, but who for whatever reason, end up not getting a plaque in Cooperstown. Dave Parker perfectly exemplifies that small group of players. For about five to seven years he was either the best player in baseball, or in the discussion. He was similar to Frank Robinson: a tall, strong, but fast outfielder. Both had slugging power and long legs, but Parker had a much better arm. Still, circumstances led to detours that kept Parker from joining the elite brotherhood in the Hall of Fame. 

If you want to cut to the chase: money ruined Dave Parker’s career. Prior to the 1979 season he inked a deal with the Pirates reportedly worth more than $7 million over 30 years, and while it didn’t technically pay him $1 million per year, fans and the media looked at Parker as if he was baseball’s first $1 million player. 

The thing is: Parker deserved the money. He was coming off two consecutive batting titles, he was the best right fielder in baseball, and he had a rocket on his right shoulder. In 1978 he hit 30 home runs and he stole 20 bases, topped 100 runs, 100 RBIs, and even hit a dozen triples. When Parker was named Most Valuable Player in the National League, Cincinnati manager Sparky Anderson called him “the eighth wonder of the world.” If anyone should have been given a $7 million deal, Parker was the man. He proved a good short-term investment when he led the Pirates to the pennant and a victory in the World Series.

But things were already souring in Pittsburgh. The fans wouldn’t forgive him for not winning the batting crown again, or the triple crown for that matter. The animosity was so bad, Parker skipped the World Series victory parade. In the ensuing years he suffered knee injuries that left him gimpy and slow, he gained weight, and he became enslaved to his drug use. On the field fans became violent, and on more than one occasion Parker removed himself from home games because objects were thrown at him. Big Dave was so disliked in Pittsburgh that one scribe wrote “If Parker ran for mayor unopposed, he’d lose in a landslide.”

It’s puzzling that the Pittsburgh Drug Trials have become virtually silenced by history considering how important they were to baseball in the 1980s. In 1985 when the scandal erupted, Parker became star witness for the prosecution, exchanging immunity for spilling the beans. He implicated the drug dealers who had infiltrated the clubhouse in Pittsburgh, he listed the names of players who bought and used cocaine, and he explained how his own drug use had diminished his production and threatened his career. Predictably, fans in Pittsburgh were disillusioned by their former star. The Pirates were even more incensed: they sued Parker for fraud and eventually paid him far less than his original contract called for.

In his post-Pittsburgh years Parker was off drugs and still a dangerous hitter. He played for his hometown Reds in Cincinnati under Pete Rose. “The Cobra” took young players like Eric Davis and Barry Larkin under his wing. He was such an impressive leader that Rose once joked, “I should have given him half my salary.” Parker had one of his best seasons in 1985, and should have won the MVP, but the tarnish from the drug scandal probably cost him the hardware.

After Cincy, Parker was the DH on two Oakland teams that won the pennant, and he won his second World Series title with the A’s in 1989. In Game One of the World Series against the Giants, Parker hit a home run, his last homer in the postseason.

With Milwaukee in 1990 when he was 39 years old, Parker had a comeback season, batting .289 with 176 hits, 21 homers and 92 RBIs and making the All-Star team. He shepherded young Gary Sheffield into the big leagues while with the Brewers, and moved on to Anaheim for one final season in 1990 but his knees were so far gone that even being a designated hitter was nearly impossible. 

Despite the drug use and injuries, Big Dave still managed more than 2,700 hits, 339 career home runs, and 1,493 RBIs in his 19-year career. He spent the mandatory 15 years on the Hall of Fame ballot, but his highest support was 24.5 percent in his second year. The drug scandal and the failure to match the great seasons he had in his twenties hurt Parker’s image and chances for the Hall. Parker let all that money change who he was, and his legacy paid the price for it. 

17. Bill Mazeroski

The best fielding second basemen in history, according to Career Runs Saved, are in order:

1. Bill Mazeroski
2. Frank White
3. Willie Randolph
4. Nellie Fox
5. Dustin Pedroia
6. Mark Ellis
7. Lou Whitaker
8. Ian Kinsler
9. Mark Lemke
10. Bobby Grich

According to that stat, Maz saved twice as many runs as the ninth and tenth players on the list. All of these second basemen were very good at picking it, but Mazeroski’s reputation was the most impeccable.

He was called “No Touch” because he transferred the ball so quickly on the pivot. His range up the middle was amazing, he made plays beyond the bag in shallow center field that most people had never seen before, and his arm was very strong.

As he left spring training to head north with the Pirates in 1960, Mazeroski was intent on having a comeback season. The previous year his batting average had plummeted more than 30 points and his home runs went from 19 to 7. He blamed the extra twenty pounds he added during the 1958-59 offseason. Entering 1960, Maz displayed the confidence you often find in youth. “The one big thing in my favor is that I’m still young, only 23,” Mazeroski told The Sporting News in March. “I still have some years ahead of me. I have a lot to make up for in 1960.” I’d say that home run in Game Seven did the trick.

Bill James wrote “Mazeroski’s defensive statistics are probably the most impressive of any player at any position.” Still, when Mazeroski was elected to the Baseball Hall of Fame by the veterans committee, Hank Aaron criticized the selection. Which shows that you can be smart, be a great player, and watch a lot of baseball and still underestimate the importance of defense.

16. Tommy Leach

Tommy Leach and Honus Wagner came up with the Louisville Colonels at the same time and both moved to Pittsburgh after the franchise was transferred there a few years later. The two played fourteen seasons together, usually hitting 3-4 in the lineup, Tommy first. They were different types of people, different physically, but they were good friends and shared a lot of train rides together.

Leach was only 5’6 and 135 pounds when he was signed by Louisville in 1898. He was from western New York, grew up only a few houses away from the Delahanty’s, who sent five boys to the major leagues. At his first professional stops, Leach was fast, a hustler, and he distinguished himself with his glove, but early on he was overmatched at the plate. After finally breaking through with the bat, New York briefly gave Leach a tryout, but shooed him away, owner Andrew Freedman saying, “We don’t take midgets on the Giants.” Louisville wasn’t as picky, and owner Barney Dreyfuss plunked down $650 for Leach. He played 16 years for Dreyfuss.   

15. Pie Traynor

Most sources claim Harold Traynor received the nickname “Pie” because he liked to eat pie. A few stories go around that little Harold stole a pie from a neighbor. Some others insist a neighborhood friend noted Harold’s “pie-shaped” face. The truth is more interesting. According to clippings in his Hall of Fame Library player file, Traynor owed his nickname to an observation made by his father. Jimmy Traynor was employed as a typesetter at the Boston Transcript, a job that was painstaking and required great skill. In those days a typesetter had to hammer in place the wooden sledges that made the type for the printing press. If a mistake was made or a slot was not properly filled, the type would fall out the bottom. This was called “pied type” or “pieing.” It was a disaster that resulted in a lot of cleanup work. According to an interview he gave late in his playing career, Traynor claims one day his father saw what trouble he was getting into and said he was “like pied type.” Is it true? No one in the Traynor family knows, but it’s a nickname origin story that doesn’t fit the common narrative.

14. Andrew McCutchen

The title of best center fielder in the history of the Pirates comes down to three men: Max Carey, Andy Van Slyke, and Andrew McCutchen. The enigmatic Al Oliver rests just outside the boundaries of this argument. 

Carey played his first game in the major leagues the same year that Jack Johnson beat Jim Jeffries for the heavyweight title. Johnson was a black man and Jeffries was not, and the event sparked racial riots across the country. The year was 1910. Carey was a great base stealer, covered vast amounts of grass in the outfield, and was a switch-hitting leadoff batter. He was sort of the Willie Wilson of his time. He played in a much different era of baseball than we see now. 

Van Slyke was a big, strong man, but he could run very well. He was almost like a tight end out in center field, loping with long strides and heavy footsteps. He was a very effective defensive outfielder and a passionate competitor. 

McCutchen is compact and strong, but quick. After a couple seasons as a leadoff man, he transitioned to the number three spot, where he increased his power. Of the three, Cutch is the only one to have won an MVP. He’s not as good a defender as Van Slyke, but McCutchen is pretty damn good. He’s extremely likable, a team leader, in the mold of Kirby Puckett. 

McCutchen’s career value was nearly identical to Van Slyke’s, but the latter played many seasons for the Cardinals. Cutch’s peak was better than Carey or Van Slyke by far. Carey is the only one to have won a World Series with the Bucs, and he’s in the Hall of Fame. Still, the numbers choose McCutchen as the greatest center fielder in the history of the Pittsburgh Pirates.

13. Sam Leever

Relied on a fantastic curve ball and good control to win 194 games in 13 seasons, all spent with Pittsburgh. He won 66 percent of his decisions, one of the ten best rates in baseball history.

Leever was the best friend of teammate Deacon Phillippe, who won 189 games and was in the same pitching rotation with Sam for eleven years. Phillippe, Honus Wagner, and Leever frequently took hunting trips together.

12. Bob Friend

Friend used a heavy sinker to coax groundballs, and with Bill Mazeroski and Dick Groat behind him, that was an excellent strategy. The big man they called “Warrior” won 191 games for Pittsburgh, topping 15 in a season five times.

11. Ralph Kiner

Kiner was major league-ready when he was 21 years old. But at that time he was flying anti-submarine missions for the U.S. Navy in the Pacific. As a rookie in 1946 he led the National League in home runs. He did the same thing for the next six years.

After he was traded to the Cubs (following protracted and nasty contract squabbles with the Pittsburgh front office), Kiner played in the same outfield with Hank Sauer. Both were dreadfully slow outfielders with weak throwing arms. The center fielder was Frank Baumholtz, a former college basketball star who could run, or at least he could run a helluva lot faster than the outfielders flanking him. When a ball was hit in the gap, Kiner and Sauer would frequently holler “You have plenty of room, Frankie!”

10. Fred Clarke

One of the most integral figures in the history of the Pittsburgh Pirates, Fred Clarke was player-manager during the deadball era, establishing the team as one of the most successful in baseball. Leading the team from his position in the outfield, the Bucs won four pennants and one world championship, and his teams won nearly 60 percent of their games. Under Clarke, the Pirates favored defense, pitching, and aggressive baserunning. He engaged in numerous battles with the other two dominant managers in the league at that time, John McGraw of the Giants and Frank Chance of the Cubs.

Clarke found his way to Pittsburgh under odd circumstances. In 1894 he was playing for Savannah in the Southern Association when his team found themselves stranded in Tennessee, unable to get back home. Barney Dreyfuss, owner of the Louisville team, wired the money needed to rescue the Savannah team. In return, he asked for Clarke to be transferred to his club. Dreyfuss later brought Clarke with him when he moves his franchise to Pittsburgh. Fred played 18 seasons for Dreyfuss. 

Clarke’s innovations extended beyond the Burgh of Pitt, he invented a type of flip-down sunglasses, developed a new pitching rubber, and pioneered a mechanical method for rolling a tarp on and off the field. He spent sixteen years as the dominant personality of the Pittsburgh club until he retired with wealth and fame following the 1915 season, the winningest manager in baseball history to that point.

In his first retirement from baseball, Clarke bought a large tract of land and established Little Pirate Ranch in Kansas. But Dreyfuss summoned Clarke from retirement in 1925, seeking a spark for what he considered an underperforming team. Clarke, who also owned stock in the Pirates, was not hired as manager, but rather accepted a controversial role as “assistant to the manager”, who happened to be Bill McKechnie. The two men circled each other for the two seasons they shared the dugout, and initially the uneasy combination succeeded. The Pirates won 95 games in 1925 and captured their first pennant since Fearless Fred had guided them to the flag sixteen years earlier. The Pirates proceeded to win a thrilling seven-game World Series and Clarke received a share of the credit. One sportswriter wrote: “No one has learned just what prompted Barney Dreyfuss … to bring his former manager back into active service. The logical conclusion is that after the Pirates missed three or four pennants that seemed to be within their grasp, Dreyfuss decided that something was lacking and that Clarke could supply that particular something. He did.”

After a less successful follow up season sitting on the bench next to McKechnie, Clarke’s second retirement stuck: he returned to Little Pirate Ranch and tended to cattle. He was a land baron and a millionaire, and in 1945 he became a Hall of Famer when the veterans committee elected the famed Pirate to Cooperstown. 

9. Barry Bonds

Eight players have had at least 1,000 hitless games. That’s an 0-for-1, an 0-for-2, and so on, any game with at least one at-bat and no hits. Among those eight, Bonds has the highest on-base percentage in hitless games. In games without a hit and with at least one ball put in play, Bonds was 0-for-2964, but he walked 917 times for a .243 on-base percentage.

8. Wilbur Cooper

Arrived as Sam Leever and Deacon Phillippe were fading out, and teamed with Babe Adams for a dozen seasons in the Pitttsburgh rotation. Cooper won a franchise record 202 games, a figure that remains out of reach nearly a century after his final victory.

Many historians consider Cooper to be the greatest pitcher in Pirates’ history. He was a quick worker and he topped twenty wins four times.

7. Max Carey

Extremely private, Carey played twenty years in the major leagues and let few people get close to him. A teammate once said, “Max gets out of the clubhouse faster than he runs the bases.” Carey spent 17 seasons in a Pirates’ uniform and only counted one good friend on the team: Honus Wagner, who reluctantly mentored Carey when the youngster arrived in 1910 and proclaimed he was “here to take the shortstop job.” He played his first six seasons under Fred Clarke, but the two men quarreled and Carey was ecstatic when Clarke stepped aside as manager for the 1916 season. Later, Clarke returned as a bench coach and the two men fought after several incidents in the dugout boiled over.

6. Babe Adams

Adams had only 12 big league wins to his credit when he was tapped by Fred Clarke to start three games in the 1909 World Series. A scout had noticed that Adams was very similar to a pitcher in the American League who had stymied the Detroit Tigers. That scout was right: Adams beat Detroit three times in the Fall Classic. He went on to win 194 games for the Bucs, his last when he was 44 years old.

5. Willie Stargell

People probably said more nice things about Willie Stargell than any player in history, with the possible exception of Mariano Rivera. Maybe Bobby Doerr is in that conversation. When the Pirates held “Willie Stargell Day” in 1980, Houston second baseman Joe Morgan sent a telegram that read: “Some people are only superstars statistically, but you are a .400 hitter as a person. When I grow up, I want to be just like you.”

4. Arky Vaughan

Like Alex Rodriguez, Robin Yount and Alan Trammell, Vaughan was a regular at the age of 20. But Vaughan was the least polished as a fielder, he averaged 40 errors per year in his first nine seasons. The Pirates enlisted Honus Wagner to tutor him, and the two even roomed together for a while. He settled in at shortstop and was passable, but it was a shift to third base that helped calm him down the last half of his career.

As a hitter, Vaughan rates third behind Rodriguez and Wagner. He was a left-handed batter somewhat like Tony Gwynn, hitting the ball the opposite way a lot. He was very patient, he led the league in walks three times, and his career walk-to-strikeout ratio was an impressive 3-to-1. Among players with at least 2,000 hits, that ranks third behind only Joe Sewell and Tris Speaker.  

Vaughan was only 40 years old when he drowned in Lost Lake in North Carolina. He was reportedly trying to save his friend, who could not swim.

3. Paul Waner

Waner was convinced that alcohol was the secret to his baseball success, and he enjoyed plenty of both. He hit over .350 six times and had a cool .333 career average. In 1927, just his second season, he won the batting title, banged out 237 hits, and was named Most Valuable Player in the National League. That year he drove his brother Lloyd in 65 times, a record for most times one batter drove in another. He did it all while he was blasted.

“When I walked up there with a half-pint of whiskey fresh in my gut, that ball came in looking like a basketball. But if I hadn’t downed my half-pint of 100 proof, that ball came in like an aspirin tablet,” Paul said.  

2. Roberto Clemente

George Sisler said of Clemente: “He’s a bad-ball hitter and would be better if he hit a good pitch. But that would take away his aggressiveness.”

1. Honus Wagner

Wagner was a freak, one of those athletes who seemed genetically a generation ahead of his time. Like Wilt Chamberlain and Jim Brown, Joe Louis and Gordie Howe, and of course Babe Ruth a decade or so later, Wagner was just better than everyone else. He could throw harder, run faster, hit the ball farther than anyone else. The game came easy to him, and he could outthink the other players on the diamond too. John McGraw said that no shortstop he ever saw could go as deep in the hole to get the ball like Honus. In comparison to his league, Wagner’s statistics are more impressive than anyone other than the Bambino.