After a miserable 69-93 campaign in 2019, the Pittsburgh Pirates' braintrust seems to have finally acknowledged that they need to rebuild. The club has already begun trading the limited valuable assets it has -- take outfielder Starling Marte, for example -- and we can expect that narrative to continue into 2020 if the season is played.
Before that, however, comes the MLB Draft, where the Pirates hold three of the top 44 selections , including the No. 7 overall pick. In theory, Pittsburgh should (emphasis on should) bolster their farm system in the Draft, but it's really never that simple. Look no further than the organization's dimwitted decision to deal top prospects Austin Meadows and Tyler Glasnow, who have since developed into studs for the Tampa Bay Rays. Even former draftee Gerrit Cole only spent five seasons with the team before he blossomed into a superstar in Houston.
Of course, in addition to squandering talent, the Pirates have also managed to completely botch some draft picks throughout their 139-year history. With this in mind, let's highlight their four worst selections of all time.
4. Bobby Bradley
You know a draft pick didn't pan out when his name doesn't even come up in a search on Baseball Reference. The Pirates drafted Bobby Bradley with the No. 8 overall pick in 1999. Let's keep this one brief by saying that he spent six seasons in their farm system and never once cracked an appearance in the big leagues. All-Star hurlers Barry Zito and Ben Sheets were nabbed in the next two picks and outfield stud Alex Rios was taken a little later at No. 19. What on earth was Pittsburgh thinking here?
3. Mark Merchant
Once upon a time, the Pirates used their No. 2 overall selection on outfielder Mark Merchant in 1987. From there, the Oviedo High School product's entire career was spent in the minors and overseas. Not only did Ken Griffey Jr. go in the previous pick, but fellow Hall of Famer Craig Biggio was taken at No. 22 overall. There is no justifying this pick.
2. Bryan Bullington
The Pirates certainly surprised a lot of people when they selected Bryan Bullington with the No. 1 overall pick back in 2002. To say he didn't live up to that billing would be a colossal understatement. The Ball State product appeared in just 18.1 innings for the club, across which he posted a 5.89 ERA. For his career (five seasons), he finished 1-9 with a 5.62 ERA and 1.580 WHIP. By drafting Bullington, they missed out on the likes of BJ Upton, Cole Hamels, Nick Swisher, Zack Greinke, Prince Fielder, Matt Cain and Scott Kazmir. We'll hazard a guess and say that Pittsburgh wishes it could have that one back.
1. Daniel Moskos
Daniel Moskos is rightfully tabbed as the poster child of poor Pirates drafts. The thing is that there...isn't much to say about the former Clemson reliever. Pittsburgh used the No. 4 overall pick of the 2007 Draft and his career literally spanned 24.1 innings. Among the players drafted after Moskos were Matt Wieters (No. 5), Ross Detwiler (No. 6), Madison Bumgarner (No. 10), and Jason Heyward at No. 14. Talk about a gargantuan swing and a miss by the Bucs.