10 biggest draft busts in Pittsburgh Pirates franchise history

For most of their history — and especially in recent years — the Pittsburgh Pirates have been on the outside looking in.

They haven't won the World Series since 1979. They've been to the playoffs just three times since the the turn of the millennium. They haven't even won a division title since 1992, before the NL Central was even formed.

It's easy to point to a lot of reasons for their long-running struggles — repeatedly frugal ownership, poor management and roster decisions, etc. — though their proclivity for misfiring in the MLB draft may be the most prominent.

These poor draft decisions, colloquially referred to as "busts" by sports fans, don't necessarily define a franchise's history, though an egregiously timed one could sink an entire era of a team. Think about how much longer the Kansas City Royals could have stretched their mid-2010s World Series window if Bubba Starling had adequately replaced Lorenzo Cain as planned.

Our picks for the Pirates' biggest draft busts of all time are listed in descending order here, though you could make a good case for them to rearranged in nearly any sequence. Heck, you could make a strong case for players not even on this list to be in the top five. That's how many busts the Pirates have had since 1965, when the first iteration of the modern MLB draft took place.

Note that for a player to be considered here, they must have actually been drafted and signed by the franchise. Thus, someone like Mark Appel, one of the most infamous busts in recent history, doesn't count, even though the Pirates originally drafted him with the eighth overall pick in 2012.

Lastly, it's important to acknowledge what a "bust" actually is. In order to qualify for such a label, a player has to have some hype and momentum in their profile. You can't let anyone down if no one has expectations for you in the first place. As such, expect to see mostly first-round picks on this list.

Without further ado, let's dive into the 10 biggest draft busts in Pittsburgh Pirates history.

10 biggest MLB Draft busts in Pittsburgh Pirates history

10. Henry Davis, C, Round 1 (1st overall, 2021)

Is it too early to put Davis, one of the team's two starting catchers in 2025 (alongside Joey Bart) on this list? Maybe, but for a first overall pick, he sure hasn't lived up to the hype.

Having played roughly 150 games of MLB action through the 2025 All-Star break, Davis is slashing .196/.277/.316 for his career. He's got a near-20-percent difference between his career strikeout and walk rates, and his 62 wRC+ suggests he's been 38% worse than a league-average hitter since making his debut in 2023.

The good news is he's put a lot of work in behind the plate and become a strong defensive catcher. That's a really positive development considering how porous his defense and bat were in right field over the past few seasons.

There's still time for the 2021 No. 1 overall pick to figure things out at the MLB level, but it's going to take an historic turnaround just for him to approach being an average hitter. Turning into a defense-first backup catcher is hardly what the Pirates foresaw when they made him the first pick in his class.

9. Will Craig, 1B, Round 1 (22nd overall, 2016)

Will Craig shot up draft boards after winning ACC Player of the Year at Wake Forest as a sophomore, hitting .382/.496/.702 with 13 home runs and 58 RBI.

Thus, the Pirates leapt at the chance to grab him in the latter half of the first round of the 2016 MLB Draft, a decision they'd soon come to regret. He performed well enough in the minor leagues — posting a .772 OPS in 2,060 career plate appearances — though his huge strikeout totals derailed the hype train before it ever left the station.

He received four at-bats in his 2020 MLB debut before being designated for assignment. After being outrighted back to Triple-A, he received another 60 at-bats the following season for the Pirates before being DFA'd again, which would all but end his time in professional baseball in the states.

His career "highlight", when Javier Baez somehow hypnotized him into forgetting the rules of baseball, stands as one of the most embarrassing moments in Pirates history, and is a defining clip of the last decade of Pittsburgh baseball.

8. Daniel Moskos, LHP, Round 1 (4th overall, 2007)

After starring at Clemson University, the Pirates thought highly enough of Moskos, a left-handed starter, to hand him a $2.475 million signing bonus as the fourth overall pick of the 2007 MLB Draft.

He had some solid years down on the farm, but by 2010, the Pirates converted him to relief, and he would make his MLB debut in 2011. It was a solid enough rookie year, as Moskos, primarily used as a lefty specialist (or LOOGY, as they used to be called), fired off a 2.96 ERA in 31 appearances spanning 24 1/3 innings.

And then... that was it. He began the 2012 season in the minors, getting DFA'd at the end of June as they cleared out 40-man roster spots ahead of the trade deadline. He was claimed off waivers by the White Sox and never appeared in the majors again.

He simply never developed the control or arsenal to be an effective starter in the big leagues, and the Pirates' inability to turn him into an MLB-caliber arm remains a stain on their pitching development legacy.

7. Mike Bielecki, RHP, Round 1 (8th overall, 1979)

There are few minor league seasons as legendary as Bielecki's 1984 season, as he won Baseball America's Minor League Player of the Year award on the back of a 19-3 record. That year, the PCL's average ERA was 4.58; Bielecki authored a 2.97 figure that led the league by a country mile.

All looked to be going swimmingly for the eighth overall pick in the 1979 MLB Draft, and he made his MLB debut September 14, 1984.

Unfortunately, that's where the good times would come to an end, as Bielecki failed to establish himself as a mainstay in Pittsburgh's rotation, only tossing more than 50 innings once (1986). He wrapped up his tenure in the Steel City with a 4.57 ERA and 1.502 WHIP in 244 1/3 innings, and he was traded to the Chicago Cubs prior to the 1988 season in exchange for Mike Curtis.

Though it doesn't factor into our rankings, it only hurts more that as soon as his tenure ended in Pittsburgh, he became a solid starter for the Cubs, finishing ninth in NL Cy Young voting in 1989.

6. Tony Sanchez, C, Round 1 (4th overall, 2009)

You know a guy is a bust when his most memorable career highlight is chugging beers after the team clinched a Wild Card spot.

Another top-five pick, Sanchez simply never lived up to his draft billing. He had an historic career at Boston College, becoming the highest MLB draft pick in school history, though his success never translated over to the pros.

The rare bat-first catcher, Sanchez had some prolific seasons in A-ball, though he began to struggle as he climbed the minor league ladder. He made his MLB debut on June 21, 2013, and though he provided some tolerable production from the catcher position — .259/.303/.378 slash line in 155 plate appearances with the Pirates — his defense remained indefensible.

He was cut loose by the franchise after the 2015 season, and he failed to latch on elsewhere. At least he was around for all three playoff campaigns, right?

5. Rick (Rich) Renteria, INF, Round 1 (20th overall, 1980)

Rick Renteria, who went by "Rich" during his playing days, gave the Pirates -0.1 WAR and 12 total at-bats after being selected in the first round.

I probably don't need to continue beyond that to justify Renteria's spot on this list, but as the rare high school draft pick on this list, it bears mentioning that the Pirates gave up on the future manager when he was just 24 years old.

Now, he didn't develop into anything special in his other career pitstops — though he was a pretty darn good pinch-hitter for the Marlins in the early-1990s — but it's still pretty amazing how quick the Pirates knew they fumbled the pick, considering he was still posting an OPS over .700 in Triple-A in 1986.

Nevertheless, Renteria remains one of the most prominent busts in franchise history, and he's better known now as the guy who lost his job to Joe Maddon just before the Cubs won their historic World Series.

4. Travis Swaggerty, OF, Round 1 (10th overall, 2018)

Oh boy. Now we're getting into real bust territory.

Swaggerty's story is more of a tragedy than anything, as he turned into a superstar prospect at the University of South Alabama after not getting selected at all in the 2015 MLB Draft.

Then, after emerging as a top-100 prospect in the Pirates' system, Covid-19 shut down the 2020 minor league season, hampering the outfielder's development. He returned in 2021 but underwent a season-ending shoulder surgery after just 12 games.

He never really returned to form after that, making his MLB debut in 2022, but notching just one hit in nine at-bats. Eventually, recurrent migraines and a health issue with his wife took their toll, and after slashing .200/.278/.369 in 17 games with Triple-A Indianapolis in 2023, he was released from the organization.

3. Chad Hermansen, OF, Round 1 (10th overall, 1995)

For a guy who was supposed to be the Pirates' center fielder of the future at the turn of the millenium, Chad Hermansen really didn't want to be the Pirates' center fielder of the future.

Another first-round high school pick, Hermansen became a top-50 prospect in the late 1990s, and he would eventually go on to earn the dreaded "Quadruple-A" label.

Owner of a career .804 OPS at the Triple-A level in 2,810 plate appearances, Hermansen was an outright detriment to the Pirates at the MLB level. He slashed .199/.257/.341 in 458 plate appearances over parts of four seasons, offering Pittsburgh -2.8 Wins Above Replacement.

If there's any consolation to this pick, it's that Hermansen gave the Cubs -0.6 WAR after being traded for Darren Lewis during the 2002 season.

2. Bryan Bullington, RHP, Round 1 (1st overall, 2002)

These next two players really belong on a tier of their own in my opinion, as there's a special status that comes with being a top-two pick in the draft.

As the No. 1 overall pick in the draft, you'd expect Bullington to be the best prospect available. Unfortunately, that wasn't really the case, as he was a safe pick made with signability in mind.

He was okay in the minor leagues, though he never emerged as a true top pitching prospect. Plus, he underwent labrum surgery and missed all of the 2006 season, an injury that all but ended his chance of emerging as an elite talent.

He did return to pitch 17 innings for the Pirates in 2007, though they weren't very effective. In all, he gave the Pirates a 5.89 ERA in 18 1/3 innings, good for -0.2 WAR, before getting DFA'd halfway through the 2008 season.

In case you really want to feel bad about this pick for some reason, here's a list of just some of the players selected after Bullington: Melvin Upton Jr., Zack Greinke, Prince Fielder, Cole Hamels, and Matt Cain. Yikes.

1. Mark Merchant, OF, Round 1 (2nd overall, 1987)

There's a lot of arguments to be made for this No. 1 spot, but all of the nine players above have something in common: they made the major leagues.

Now, some of them provided the Pirates with negative value, which you can argue is worse than someone who didn't even play a game for the big league team. But, as one of just five No. 2 overall picks to never make it to the big leagues, Merchant is an obvious selection for this top (bottom?) spot.

He lasted just three years in the Pirates' organization before getting shipped off to Seattle, never reaching Double-A with the team that drafted him.

And, for what it's worth, the lone guy picked ahead of Merchant in the 1987 MLB Draft ended up being pretty good at the whole baseball thing. Maybe you've heard of him: Ken Griffey Jr.