First Pitch: Looking Back for the Quickest Turnarounds in Pirates History

The Pittsburgh Pirates finished with a 69-93 record way back in 2019, giving them a .426 winning percentage on the season. It’s the 28th time in team history that they finished with a winning percentage of .426 or lower. I wanted to look at each of those prior 27 seasons and see how far they were from the next time they made the playoffs. It doesn’t guarantee anything, but it’s a fun exercise in history. I started with the worst team and moved in order to the two seasons where the Pirates finished with a 69-93 record before 2019.

The worst record in team history was the 1890 season, which was special circumstances with the best players leaving the NL (and American Association) for a player-formed league aptly called the Player’s League. They finished 23-113 that season and they were 11 years away from winning their first National League title. There was no World Series in 1901-02, but they Pirates won three straight titles, including the 1903 season.

The second worst season was 42-112 in 1952. That was eight years prior to their third World Series title.

The 1883-84 seasons in the American Association are the third and fourth worst seasons in team history. As you can figure out from the 1890 season, they were far away from making the playoffs/winning a league title.

The 1953 Pirates improved by eight games over the aforementioned 1952 squad and they were one year closer to that 1960 WS title.

The 1917 Pirates were awful in Honus Wagner’s last season. They were eight years away from both their first (1909) and second World Series title (1925).

The 1954 club improved just three games over the prior season, while moving one step closer to that 1960 title.

The 2010 Pirates provide the first glimpse of hope. They went 57-105, but they were just three years away from making the playoffs three straight times.

The 1985 Pirates were really bad, going 57-104. They were five seasons away from a three-year playoff run.

Here’s one you don’t like to see. The 1952-54 Pirates improved slowly each year, but the 1950 club was better than any of those teams, going 57-96.

The 2001 Pirates celebrated the first year at PNC Park with a 62-100 record. They were a dozen years away from the playoffs.

In 2009, the Pirates avoided 100 losses with a little help from Mother Nature. They went 62-99, then made the playoffs four years later.

The 1955 club continues the improvements over the previous two seasons. They were seven games better than the 1954 team, ten games better than 1953 and 18 games better than 1952.

After their poor season in 1985, the Pirates improved by 6.5 games in 1986.

The 1947 Pirates added Hank Greenberg to Ralph Kiner, and also acquired manager/player Billy Herman, giving them three Hall of Famers. They finished 62-92.

The 1957 Pirates were slightly better than the 1955 club, improving by two games. The problem is that the 1956 club was better than both years, so they took a step back in 1957 after improving for four straight seasons. The bright side, just three years away from a World Series title.

The 1995 Pirates finished 58-86 during the strike-shortened season. They were another year away from the 1990-92 playoff run and far from making the playoffs again.

The 1891 team improved by 32 wins over the previous season and they were still an awful disappointment. The Pirates added a lot of talent between 1890-91 and they still finished 55-80.

The 1946 Pirates, minus the two Hall of Famers they added for 1947, finished one game better than that team.

The 2005-06 teams finished with identical 65-97 records, which was far from encouraging, but it got much worse when the 2007 club was one game better and the 2008 team was back to 65-97. Four straight years averaging 65.25 wins.

As you saw above, the 1952 club was downright awful and the 1950 team wasn’t much better. The year between, the Pirates made some progress that was quickly erased, improving by 6.5 games over 1950. That was followed by a 22-game drop in 1952.

The 1916 club wasn’t as bad as the 1917 club, but they weren’t that good either. They finished 65-89.

The first time that the Pirates were 69-93 in a season was 1998. Then they did it again two years later. These were near the start of their bad stretch, though two of the best seasons during “the streak” were 1997 and 1999.

So the best example of a quick turnaround from a very poor season is the 1957 club going from 62-92 to 95-59 (and a World Series title) in just three years. You also have the 2010 team going from 57-105 to 94-68 and a playoff spot in just three seasons.





By John Dreker

On this date in 1975, the Pittsburgh Pirates traded pitcher Wayne Simpson to the Philadelphia Phillies in exchange for outfielder Bill Robinson. Simpson, a 26-year-old starting pitcher, played four seasons in the majors (1970-73) prior to the trade, going a combined 29-19, 4.08 in 88 games, 79 as a starter. He was an All-Star as a 21-year-old rookie in 1970, going 14-3, 3.02 in 26 starts, After coming over from the Royals in a March 1974 trade, he spent the entire 1974 season at Triple-A for the Pirates, where he went 9-10, 3.32 in 160 innings. Robinson was 31 years old, coming off a 1974 season in which he hit .236 with five homers in 100 games. Just one season earlier, he had hit .288 with 25 homers for the Phillies.

Following the trade, Robinson played eight seasons for the Pirates. He saw plenty of time at 3B, 1B, RF and LF over the years. In 805 games with Pittsburgh, he hit .276 with 109 homers and 412 RBIs. In 1977, he hit .304 with 26 homers and 104 RBIs, with all three being career high numbers during his 16 seasons in the majors. Simpson pitched just seven games for the Phillies in 1975, then was sold to the Angels prior to the 1976 season. After a full season in the minors, Simpson pitched 122 innings for the 1977 Angels, posting a 6-12, 5.83 record. That was his last season in the majors.

Jung-Ho Kang, third baseman for the 2015-19 Pirates. Kang was a major international signing for the Pirates during the 2014-15 off-season. He was already an established star in Korea before joining Pittsburgh at 28 years old. As a rookie in 2015, he hit .287 with 15 homers and 58 RBIs. A late season knee injury cost him the end of the 2015 season and the start of the next year. In 103 games in 2016, he hit .255 with 21 homers and 62 RBIs. He would miss the following year due to suspension for drunken driving, then return in 2018 at the end of the season for three games. Kang was with the Pirates for part of 2019 and hit ten homers in 65 games, but he had a .169 batting average and was released in early August.

Lastings Milledge, outfielder for the 2009-10 Pirates. He was a first round draft pick of the Mets in 2003. After two seasons in the majors, New York traded him to the Washington Nationals. In 2008, Lastings played his first full season in the majors, hitting .268 with 14 homers, 24 stolen bases and 65 runs scored in 138 games. He was sent to the minors early in the 2009 season and the Pirates acquired him, along with Joel Hanrahan, in exchange for Nyjer Morgan and Sean Burnett on June 30, 2009. Milledge hit .291 with 20 RBIs in 58 games for the Pirates in 2009. In 2010, he played 113 games for Pittsburgh, hitting .277 with a .712 OPS and 34 RBIs. He was granted free agency after the season, signing with the Chicago White Sox, where he played two games during the 2011 season. He signed to play in Japan for the 2012 season and remained there for four seasons. He played in Mexico in 2016 and then independent ball in 2017.

Rennie Stennett, second baseman for the 1971-79 Pirates. The Pirates signed him as an amateur free agent in 1969 and it took just two seasons for him to have an impact in the majors at 20 years old. After coming up in early July of 1971, he hit .353 in 50 games for the Pirates. In 1972, he saw time at five different positions (SS/2B/OF) and hit .286 in 109 games. The 1973 season saw Stennett mostly at 2B/SS, playing just five games in the outfield. He played 84 games at second base and 43 at shortstop. He struggled at the plate, hitting .242 with only 16 walks in 128 games, although he did connect for a career high ten homers.

Stennett had a strong season in 1974 as the Pirates everyday second baseman. He played 157 games, hitting .291 with 84 runs scored and 196 hits. In the playoffs however, he hit .063 in the four-game series against the Dodgers. The 1975 season was much like the prior year. He hit .286 with 62 RBIs and 89 runs scored, helping the Pirates to the playoffs again. This time against the Reds, he went 3-for-14 with three singles and no runs or RBIs. On September 16, 1975, the Pirates beat the Cubs 22-0 and Stennett went 7-for-7 at the plate with five runs scored, tying Wilbert Robinson’s record for seven hits in a nine-inning game. In 1977, Stennett finished second to teammate Dave Parker in the NL batting race, hitting .336, while also adding 28 stolen bases. It was the only full season of his career that he batted over .300. In each of his four seasons following 1977, he failed to reach the .250 mark.

Following the 1979 World Series, Stennett became a free agent and signed with the Giants, where he finished his career two seasons later. While with the Pirates he .278 with 458 runs scored and 1,122 hits in 1,079 games. In 1974 and 1976, he led all NL second baseman in putouts. He received MVP votes during the 1974 and 1977 seasons. Stennett played over 100 games in eight straight seasons with the Pirates.

Wid Conroy, shortstop for the 1902 Pirates. He played five seasons in the minors before making his Major League debut with the 1901 Milwaukee Brewers (current day Orioles). He hit .264 with 64 RBIs, 74 runs scored and 21 stolen bases in 131 games. Conroy jumped his contract at the end of the season to sign with the Pirates for 1902. Playing shortstop before it became Honus Wagner full-time position, Conroy hit .244 with 47 RBIs and 55 runs scored in 99 games. He played strong defense, finishing third in fielding percentage among NL shortstops. As soon as the season ended, he jumped from the Pirates back to the AL to join the New York Highlanders. He played another nine seasons in the majors, finishing with a .248 average, 605 runs scored and 262 stolen bases in 1,374 games. After his big league career ended, he played another six seasons in the minors.

Bill Gray, third baseman for the 1898 Pirates. He made his pro debut with the Phillies in 1890 as a teenager. After two seasons with Philadelphia, he spent three years in the minors. He returned to the majors with the Cincinnati Reds in 1895 and hit .304 in 52 games. The following season his average dropped down to .207, which would lead to him spending the 1897 season back in the minors. On November 10, 1897 the Reds traded him, along with Billy Rhines, Pop Schriver, Jack McCarthy and Ace Stewart to the Pirates for Mike Smith and Pink Hawley. Gray was the everyday third baseman for the Pirates in 1898 and he hit .229 with 67 RBIs and 56 runs scored in 137 games. His defense was below average and he committed the second most errors among NL third baseman. It ended up being his last season in the majors. The Pirates traded him that December to Milwaukee of the Western League in exchange for Ginger Beaumont, who went on to become a star center fielder for the Pirates for eight seasons. Gray finished his career two years later in the minors.

Chuck Lauer, outfielder/catcher for the Alleghenys in 1884 and 1889. A local kid from Pittsburgh, he opened up his pro career in 1883 playing for a minor league team called the Pittsburgh Liberty Stars, from the Western Interstate League. Lauer started playing for the Alleghenys during July of 1884 as an outfielder. At the end of the season, with his team near the bottom of the American Association standings, Lauer took the mound three times and allowed 25 runs in 19 innings, picking up two losses and a tie. He hit just .114, going 5-for-44 with five singles that season. Five years later he reappeared in the majors with the Alleghenys and lasted just four games this time. He hit .188 with five strikeouts and five errors in his three games behind the plate. His only other experience in the majors was with the 1890 Chicago Colts (Cubs) and even then he lasted only two games.

John started working at Pirates Prospects in 2009, but his connection to the Pittsburgh Pirates started exactly 100 years earlier when Dots Miller debuted for the 1909 World Series champions. John was born in Kearny, NJ, two blocks from the house where Dots Miller grew up. From that hometown hero connection came a love of Pirates history, as well as the sport of baseball.

When he didn't make it as a lefty pitcher with an 80+ MPH fastball and a slider that needed work, John turned to covering the game, eventually focusing in on the prospects side, where his interest was pushed by the big league team being below .500 for so long. John has covered the minors in some form since the 2002 season, and leads the draft and international coverage on Pirates Prospects. He writes daily on Pittsburgh Baseball History, when he's not covering the entire system daily throughout the entire year on Pirates Prospects.

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