Top 10 Best Diamond in the Rough Draft Picks in Pirates History

By Jason Shetler

Here now are the ten best “diamond in the rough” picks that the Pirates have ever drafted. These players were all selected after the fifth round. 

10. Tony Womack: The Pirates chose Tony Womack in the seventh round of the 1991 draft. After being a utility player his first few seasons, he became the Pirates starting second baseman in 1997. Womack was an All-Star that year, as put up 60 stolen bases, which were most in the National League. He also stole an NL best 58 bases in 1998. 

9. Kevin Young: In the 1990 draft, the Pirates selected Kevin Young in the seventh round. He played for the Pirates from 1992 to 1995 before being released by them prior to the 1996 season where he then signed with the Kansas City Royals. Young returned to Pittsburgh in 1997, and finished his career with them until 2003. In 11 seasons total with the Pirates, he had a .762 OPS. There was a three year stretch from 1997 to 1999 in which Young posted an OPS of .862 with a 119 OPS+. 

8. Randy Tomlin: Randy Tomlin was drafted as an 18th round pick in 1988. While most look at Doug Drabek, John Smiley, Zane Smith and Bob Walk as the main contributors of the early 90’s Pirates rotation, Tomlin pitched very well during his time with the Bucs, posting a 3.43 ERA along with an ERA+ of 107 from 1990 to 1994.

7. Nate McLouth: The Pirates drafted Nate McLouth as a 25th round selection in 2000. He made his debut in 2005, and was used as a reserve outfielder his first couple seasons. 2008 was a career year for McLouth, as hit 26 home runs, the second highest single season total by a Pirates center fielder in club history. He was named an All-Star that season, and also won a Gold Glove award. From 2005 to 2009, McLouth posted a .783 OPS with a 104 OPS+. He had a second stint with the Bucs in 2012.

6. John Smiley: In 1983, John Smiley was drafted by the Pirates in the 12th round. He  pitched six seasons in Pittsburgh from 1986 to 1991 where he put up an ERA of 3.80 with a 1.19 WHIP. Smiley’s best season came in 1991 when he became an All-Star for the first time while also finishing third in the NL Cy Young voting. 

5. Bruce Kison: In the 14th round of the 1968 draft, the Pirates selected Bruce Kison. Kison’s debut season was in 1971, and he was a vital part of the rotation throughout the 70’s. During that stretch, he posted a 3.49 ERA. Kison was one of the few players who were on both of the Pirates World Series championship teams in 1971 and 1979. 

4. Bob Moose: The Pirates selected Bob Moose in the 18th round of the inaugural MLB Draft in 1965. A graduate of Franklin Regional High School, Moose spent all ten of his big league seasons with his hometown team from 1967 to 1976. He registered a 3.50 ERA along with a 2.95 Fielding Independent Pitching and helped the Pirates during their 1971 World Series title run.

3. Tony Watson: Tony Watson was drafted originally as a starting pitcher by the Pirates in the ninth round of the 2007 draft. He made his debut with the Bucs in 2011 as a reliever, and has really excelled in that role. In his first five seasons, Watson has posted an ERA of 2.46 with a 151 ERA+. He was named an All-Star in 2014, becoming the first Pirates lefty reliever in franchise history to take part in the Midsummer Classic. 

2. Mike Gonzalez: It’s not often that a 30th round pick is able to reach the Majors, but that was the case with Mike Gonzalez after being drafted in that round by the Pirates in 1997. Gonzalez arrived to Pittsburgh in 2003, and spent the next couple seasons pitching as a setup man before becoming the Pirates closer in 2006. Prior to the 2007 season, he was traded to the Atlanta Braves as part of the Adam LaRoche deal. In his four seasons with the Pirates, Gonzalez had a 2.37 ERA while posting an outstanding ERA+ of 184. 

1. Dave Parker: The unquestioned greatest find in Pirates draft history was Dave Parker. After being drafted by them in 1970 as a 14th rounder, “The Cobra” spent 11 seasons in Pittsburgh from 1973 to 1983, posting an .848 OPS along with a 131 OPS+. Aside from helping the Pirates win the 1979 World Series, Parker’s other accolades with the Bucs include being named a four-time All-Star, a three-time Gold Glove winner and the recipient of the 1978 NL MVP award. 








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