Last Updated: June 17th, 2026 by Michael Griffin
Baseball fans usually must wait the longest to see if their team drafted a star or bust. Basketball and football drafts tend to shake out quickly, while most baseball draftees must navigate the Minor Leagues and then show they belong in the Majors. However, when the busts reveal themselves … woof. We’re talking high-round mistakes here, too. The list of teams that passed on Albert Pujols and Mike Piazza would be WAY too long. Here are 12 unforgettable MLB draft day disasters that still sting, especially if you’re a fan of any teams that picked the bust.
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Yankees Draft Brien Taylor, Pass on Manny Ramirez’s Sweet Swing
With the #1 pick in 1991, the Yankees dreamed of a homegrown ace, grabbing fireballer Brien Taylor, who they envisioned as a lefty Dwight Gooden. Unfortunately, a shoulder injury sustained in a fight meant Taylor never even reached the Majors. To make matters worse, they missed out on Manny Ramirez’s legendary bat. Bronx Bomber fans could have enjoyed having Manny anchor the clean-up spot for a long time. Instead, Cleveland got that pleasure.
Astros Pass on Derek Jeter for College Star Phil Nevin
In 1992, the Houston Astros held the coveted #1 pick and used it on college slugger Phil Nevin. While Nevin carved out a solid career, he was no Derek Jeter, the skinny kid from Michigan who the Yankees famously nabbed with the sixth pick. The Astros missed their chance at a dynasty-defining shortstop, a mistake that still stings baseball fans in Houston.
Orioles Take Ben McDonald, Miss Frank Thomas’ Monster Bat
The Orioles wanted a workhorse ace, so they grabbed Big Ben McDonald with the top pick in 1989. While McDonald had a solid career, the real prize of the draft was Frank Thomas, whose monster bat was still on the board. Thomas went on to become a first-ballot Hall of Famer, leaving Baltimore to wonder what could have been with that powerful pick.
Padres Pick Matt Bush #1, Let Justin Verlander Go to Detroit
In 2004, the San Diego Padres drafted local shortstop Matt Bush with the #1 overall pick, hoping for a hometown hero. With the very next pick, the Tigers selected Justin Verlander. Bush’s career was derailed by personal issues, while Verlander is finishing up a career that will undoubtedly land him in the Hall of Fame. Oops.
Pirates Choose Daniel Moskos, Leave Madison Bumgarner on the Board
With the fourth pick in 2007, the Pirates went for lefty reliever Daniel Moskos, leaving future World Series hero Madison Bumgarner for the Giants to scoop up. While Moskos became a trivia answer, MadBum carved out a legendary October resume. It was another example of the Pirates not drafting wisely during that era.
Royals Bet on Colt Griffin’s 100 MPH Heat—Miss Out on David Wright
In 2001, the Royals couldn’t resist Colt Griffin’s radar-busting fastball, but it never translated to big-league success. Meanwhile, David Wright—picked 38th—became the beloved Captain of the Mets. The Flushing Faithful are forever grateful for Kansas City’s miscalculation.
Mets Pick Steve Chilcott First, Let Reggie Jackson Become Mr. October Elsewhere
The draft was both kind and cruel to the Flushing Faithful. The team had the first pick in 1966, and they selected catcher Steve Chilcott. How bad was this pick? He was the first No. 1 pick to never make the Majors. Even worse? The No. 2 pick was some guy named Reggie Jackson, who went on to become a Hall of Famer and World Series hero.
Marlins Draft Josh Booty, Pass on Roy Halladay’s Cooperstown Career
The Florida Marlins took a swing on two-sport phenom Josh Booty with the #5 pick in 1994, but he ultimately chose an NFL career and never reached the majors. Twelve picks later, the Blue Jays quietly selected Roy Halladay. Sure, other teams passed on Doc, but missing out on a future Hall of Famer for a player who never played an inning is a tough look.
Cubs Take Hayden Simpson, Watch Christian Yelich Become an MVP
In 2010, the Cubs surprised everyone by picking pitcher Hayden Simpson at #16. Just a few picks later, the Marlins scooped up Christian Yelich, who’d go on to win an MVP award. Imagine Yelich patrolling the Wrigley Field outfield as a member of the Cubs, not as a visiting player… OK, deep breaths, Cubbie fans.
Twins Pick Adam Johnson, Chase Utley Goes to Philly
The Twins took pitcher Adam Johnson with the #2 overall pick in 2000. Meanwhile, Chase Utley was still waiting for a call—eventually becoming a Phillies legend and World Series champ. Johnson had a cup of coffee in the bigs, but Utley had a parade. That’s a big difference.
Reds Roll the Dice on Chris Gruler, Miss Cole Hamels’ Big League Brilliance
Chris Gruler was the Reds’ pick at #3 in 2002, a hard-throwing righty whose promise was shattered by injuries before his career could begin. Fourteen picks later, Cole Hamels went to the Phillies and became a World Series MVP. The Draft is a gamble, but this one was a heartbreaker for Cincinnati.
A’s Take Ariel Prieto, Watch Todd Helton’s Rockies Legend Begin
The A’s took Cuban defector Ariel Prieto with the 5th pick in 1995, hoping for instant stardom. Instead, Todd Helton—picked 8th—became a Rockies icon, piling up hits and Coors Field memories while Prieto’s career faded into obscurity after posting a 15-24 record.