Inspired by Grant Brisbee's article on McCovey Chronicles, I used Baseball-Reference's draft search function to compile a list of the best Pirates drafted at each round. I selected players based on their accomplishments with the Bucs; only in rounds with no significant Bucco major leaguers did I go with players who they drafted but didn't sign. (If neither appeared in a given round, I opted for a draftee with a good name or interesting angle.) If nothing else, the list demonstrates that a) drafting is an elusive exercise and b) gems are available throughout the draft:
The best move of Joe L. Brown's second tenure with the Bucs. With first-rounders Andrew McCutchen, Gerrit Cole and Jameson Taillon (and heck, Pedro Alvarez and Tony Sanchez, not to mention Austin Meadows and Reese McGuire) in the organization, this may be a ranking to revisit in 10-20 years.
Easy win for the Candy Man.
Such a historically lackluster round that a pick from deep inside the Littlefield-Creech Rule 4 wasteland gets the nod: the two most successful major leaguers, Stew Cliburn and Jeff Keppinger, made their careers outside of Pittsburgh. Hoping that Nick Kingham earns this one within a few years.
It took a trade to Philadelphia for Cash to become a regular, but his five seasons of part-time play with the Bucs give him the nod. Rule V loss Bip Roberts also had a solid career. Tyler Glasnow or Justin Wilson may give cause to revisit this ranking at some point.
Effective swingman early in career; then part of the package that brought Madlock (and a world title) to Pittsburgh.
Willie Randolph was the best player the Pirates picked in this round, but all of his big-league accomplishments occurred in pinstripes. Non-signee Mickey Morandini once turned an unassisted triple play at Three Rivers Stadium, but he wore a Phillies' uniform when doing so. For his work in Pittsburgh, Young gets the nod over Matt Capps.
Most of his greatest moments happened after the Bucs let him go, but we'll always have those two and a half months of chaos-theory glory in 1992.
Jimmy Anderson has a slight edge in WAR, but I expect Watson to overtake him in the near future.
11. Milt May (1968)
Alas, the Bucs could not seal the deal with Stephen Drew in 2001.
Smiley provided the Pirates several strong seasons; Ted Simmons later flipped him for another strong lefty starter. Ron Schueler didn't sign as the the twelfth-rounder in 1966, but he showed up in Black and Gold twenty years later as Jim Leyland's first pitching coach.
Late-blooming LOOGY made six of his 467 career MLB appearances with Pirates.
Biggest steal in Bucco draft history.
Two stints in Pittsburgh, a decade apart; also pitched for ten other MLB franchises.
16. Ron Wotus (1979)
Hoping that Max Moroff will someday surpass Wotus' 32 games played/1.0 WAR.
The Bucs liked Gonzalez so much that they drafted him twice; they failed to reach an agreement after taking him in the seventeenth round in 1996, but he did sign after being drafted thirteen rounds later the following June. Rick Honeycutt, selected in 1976, had the most successful career of any Bucco seventeenth-round pick, but all of it occurred with other teams; Harding Peterson gave him away for Dave Pagan (one game pitched for the Pirates) a year after the Pirates drafted him.
18. Bob Moose (1965)
Solid career; untimely death. For such a late juncture in the draft, the Pirates have done relatively well in the eighteenth round; other selections include Dennis Rasumssen, Randy Tomlin and Joe Beimel.
The Bucs' nineteenth-round efforts have yielded eight fringy major-leaguers, none of whom has ever played a game for the Pirates (Brian Tallet's 242 MLB games represents the most substantial career of the eight). Against that checkered past, I'll give the nod to Terry Collins, the 1971 nineteenth-rounder who never played a major-league game, but served the Buccos as a successful minor league manager and major league bullpen coach. (If Kent Emanuel's arm doesn't fall off in the course of his collegiate pursuits, he may seize the top spot.)
Always a steal: as a Rule 4 draft pick (the first example of Mickey White's rose-blooms-in-the-desert later-round competence to appear on this list), as a Rule 5 draft pick, and as a trade acquisition.
Like Rick Honeycutt, a solid lefty starter who Harding Peterson gave away before he could appear in a game for the Bucs. Later, an inspiration for his perseverance in the face of injuries and cancer. Perhaps Phil Irwin will rebound from his own injury and seize this spot on the list.
Most recently seen announcing selections for Kansas City in this year's draft, the diminutive Patek played three seasons for the Pirates before departing in one of Joe L. Brown's less-impressive trading efforts.
23. Ed Ott (1970)
Five letters, very respectable middle-of-the-draft value.
A likeable utility man, but wholly inadequate to replace an injured Jason Kendall in 1999.
Mickey White's influence prevented turn-of-the century Pirates' drafts from feeling completely like sticking a needle into one's eye. Picking McLouth in 2000 was one such ray of sunshine. (Then again, the all-time most noteworthy athletic accomplishment from a Bucco twenty-fifth round pick came on a football field in California: six years after turning down the Bucs for West Virginia football, 1977 pick Fulton Walker notched the first kickoff return for touchdown in Super Bowl history.)
26. Ian Snell (2000)
Rick Reed, selected in 1986, had the best career of anyone the Bucs drafted in this round, but most of it–save for a memorable debut–occurred after the Pirates released him in 1992.
Sanford's .422 OPS over 14 games (as part of the 1998 Pirates' frustrating quest for a third baseman), gets the nod over Jeff Zaske's three scoreless appearances in 1984.
Didn't sign, but went on to play in over a thousand games with seven other franchises.
Didn't sign, but went on to pitch in over 300 games with the Brewers and Mariners. (Twelve-year-old me once took batting practice against the Bucs' 1975 twenty-ninth rounder, Mt. Lebanon High School's Richard Holloway. He said that I had a good swing.)
If you don't want to count Gonzalez twice, this round has also yielded two Bucco one-season wonders: Lou Marone (139 ERA+ in 1969; one game after that) and Kevin Polkovich (93 OPS+ as an understudy shortstop in 1997; 32 OPS+ in his only other year). Lance Johnson was the one who got away.
Won final game at Forbes Field as a rookie, rotator cuff injury ended his career a year later.
32. Doug Ault (1969)
Didn't sign, but went on to hit the first two home runs in Blue Jays' history.
Both of Pirates' 2001 and 2002 drafts yielded major-leaguers in this round; future Rule 5 loss Chris Shelton came a year before Tony Plush.
34. Page Odle (1985)
As a player, never made it past Class A, but interacted with the Buccos frequently in later years as Jack Wilson's agent.
Two respectable seaons in the rotation, early in The Streak Years.
Didn't sign, but further evidence of Mickey White's eye for later-round talent.
Convincing win over John Wehner for "Best Local Guy Bucco, 1990s Edition," as well.
A good return for a thirty-eighth round draft pick–and, alas, a good return for Matt Morris six years later.
39. Vance Law (1978)
Late-round legacy pick turned out to have a solid career as a utility man, but most of it occurred after the Bucs traded him.
Another fortieth-rounder who didn't sign, 2010's Harrison Cooney, figures to improve his standing significantly today.
Didn't sign, but had a solid run as a utility player with the Dodgers before his untimely death.
Lefty power he showed as a part-timer in 1995 and 1996 didn't quite materialize in a regular role in 1997.
Promising start to his major-league career, but ultimately didn't miss enough bats to stick around.
No major-leaguers in this round for the Bucs, but "Dexter Bobo" is a cool name.
Didn't sign, but would be linked to the Pirates in trade rumors a decade and a half later.
Best remembered for shoddy work in both the final game at Three Rivers and first game at PNC Park, but actually an excellent return on a forty-seventh round investment: from 1996-99, he pitched in 179 games (all but two out of the bullpen) and contributed a 115 ERA+. Plus, seemed like a really good dude when my friend Mike and I talked to him at the Clark Bar & Grill after a game in 1997.
His home run off Carlos Perez in May 1997 prompted Greg Brown to coin the term "Freak Show"; ultimately played in 447 major-league games.
The Pirates' were not snoozing during the late rounds of the 1992 draft: after identifying future major-leaguers Wilkins and Brown in consecutive rounds, they took a speedy outfielder from Wayne Graham's first Rice University squad. Emanuel, however, decided to return to Houston for his duties as a speedy quarterback in Fred Goldsmith's final Rice University squad. It proved to be a good career move; Emanuel played eight seasons as an NFL wide receiver, hauling in 351 passes and, by happenstance, causing a change to the league's rulebook.
Didn't sign; brief appearance in major leagues with 2010 Orioles.