- 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.
|Richie Zisk 1975 Topps|
- 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.
- 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.
- 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. 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) and 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.
|Cutch 2005 Topps Update|
- 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.