The Pirates have had a ton of bad draft picks, and unfortunately for them being a first rounder was never a lock to make it. Also unfortunately for the Pirates, the hardest thing about making this list will be choosing which ones, not coming up with ten. Fortunately for me the draft didn’t begin until 1965.
- Chad Hermansen – He was the 1995 Pittsburgh Pirates number one pick. Number 10 to be precise and he was supposed to be the answer in center field heading into the new millennia. In six years he played in 185 total games with a total WAR or -3.5. In 492 at bats he put up a .195 batting average. Unmitigated disaster might still be kind.
- Tony Sanchez – Tony had promise. It always felt like we were waiting for some part of his game to catch up to another and for a catcher in many ways that needs to be the bat catching up to the defense. Tony had a tendency to be the opposite. His most significant contribution to the Pirates was probably chugging two beers in the locker room after they clinched a trip to the post season in 2013.
- Daniel Moskos – in 2007 he was the 4th overall pick and the Pirates forked over more than 2 million dollars for the right to watch him struggle to get his footing. He appeared in 31 total games in the majors and became a lightning rod for the Pirates inability to draft pitchers.
- Bobby Bradley – in 1999 he was chosen to be the next in line for Pirates future aces. In fact from 1998 through 2003 the Pirates chose a pitcher with each of their first round picks. Don’t worry, more will be on this list. The most successful of which was, wait for it, that’s right, traded, Sean Burnett. Sean was actually a teammate of Bobby’s as they both came from Wellington Community High School in Florida. I have to write all this because honestly, who knows what happened to Bobby.
- John Van Benschoten – OK, so John wasn’t actually that bad. He showed promise and injuries never let him get a real foothold. That said he holds the record for the highest ERA with at least 75 innings pitched. The Cincinnati native could be a giant conspiracy by the Reds to kill the Buccos.
- Bryan Bullington – MLB and the Pirates number one overall pick in the 2002 draft. He was widely panned as a sign-ability selection. He never made an impact for the Pirates or anyone else. Here are some names passed on to take this prize, Zack Greinke, Prince Fielder, Cole Hamels, Matt Cain. He was a poster boy for the draft system being set up unfairly and Dave Littlefield’s ineptitude.
- Mark Alan Merchant – I’ve covered him previously, as he is still the highest drafted player (number 2 overall) to never crack the league. Injury played a huge role and Ken Griffey Jr. was number 1. \
- Joe Grigas – Drafted number 16 in the 1967 MLB Entry draft by the Pirates. He played four seasons. He never got past Single A. He never played more than 69 games in a season. Not great.
- Rich Renteria – Drafted number 20 by the Pirates in the 1980 draft, he never really made his mark. Playing in only 167 total games most successfully with the Marlins in 1993 as a pinch hitter.
- Sam Khalifa – He was to be the anchor at SS for the Buccos, and platooned with Raphael Belliard, after struggling he was sent down paving the way for Jay Bell to secure his position as the starter. He quit the game after only playing 167 in the league.
The scariest part of writing a piece like this is how easy it would be to put together a top 20. This must improve to be blunt, but the Pirates have a new sheriff in town, here’s hoping he can find gold in all five rounds the league is giving him.