- 1966 - The Pirates selected 3B Richie Hebner first (#15 overall, $40K bonus) in the amateur draft. He was a solid pick - The Gravedigger played 11 seasons in Pittsburgh, hitting .277 with 128 HR. They had a couple of other future Buccos emerge from the mix in 2B Dave Cash (#5), who played five years in Pittsburgh with a .285 BA to start a 12-year career and OF Gene Clines (#6) who spent the first five years of a 10-year MLB stint with the Bucs, hitting .287. Pitchers Ron Schueler (#12) & Rich Hand (#38) had nice big league tenures although neither signed with Pittsburgh and were chosen by other clubs in later drafts.
|Richie Hebner 1969 Topps Rookies|
- 1967 - HS outfielder Joe Grigas was the Pirates first (#16) pick in the draft, and never advanced past Class A ball. They had better luck with OF Richie Zisk in the third round. He spent six of his 13 big league seasons with the Pirates, hitting .299. The second half of his career was in the AL, where he earned a pair of All-Star berths.
- 1969 - Pittsburgh picked HS righty John Morlan first (#10) selection in the draft; he won two games over two seasons. The rest of the draft was a complete washout with OF’ers Doug Ault and John Doherty being the only selections to play 100+ MLB games. They both passed on the Pirates and joined the league in later drafts.
- 1977 - HS outfielder Anthony Nicely was the Pirates first pick (#18). He never made it to the show, but two of his draft mates did - SS Wayne Tolleson (12th round), who spent ten years in the league mostly as a reserve for Texas and the Yankees, and LHP Dennis Rasmussen (18th round), who pitched 12 seasons of MLB ball for five teams.
|Sam Khalifa 1986 Donruss|
- 1982 - High school SS Sammy Khalifa was the first (#7) Pirate pick in the draft. the good glove, bad bat infielder would play 186 MLB games. They also drafted LHP Joe Magrane in the third round, but he didn’t sign with Pittsburgh, going to the Cards in 1985 as a first-rounder.
- 1986 - The Pirates selected University of Arkansas's Jeff King‚ The Sporting News college player of the year‚ as the first overall pick in the June draft, giving him an $185K bonus. He spent eight of his 11 big league years as a Pirate, hitting .258 with 99 HR. The Bucs selected other MLB talent in OF Tom Goodwin (.268 over 14 years), SS Mike Mordecai (.244 over 12 years) and pitchers Stan Belinda (who spent his first four plus seasons as a Pirate) & Rick Reed, who started as a Pirate but blossomed as a Met and Twin.
- 2005 - Pittsburgh struck gold as Andrew McCutchen was selected in the first round (#11 overall) of the draft and was signed to a $1.9M bonus, prying the prep star away from a scholarship to Florida. That made it a great day, even though the only other selections to make it to the show were eighth round pick Steve Pearce and fourth rounder Brent Lillibridge.
|Brent Lillibridge 2005 Bowman Heritage|
- 2010 - Pittsburgh drafted high school ace RHP Jameson Taillon, inking the second overall pick for a $6.5M bonus. They also signed preppie RHP Stetson Allie in the second round for $2.5M, who fizzled as a pitcher due to control issues and was converted to a 1B/OF. The club spent $11.9M on their draft class. Texas prep RHP Nick Kingham was a fourth round pick who was signed to a $485,000 deal. Later round guys short-circuited by injuries but who made appearances in the show were pitchers Brandon Cumpton and Casey Sadler.