Last Updated: September 30th, 2026 by Matthew Brown
I've done a lot of work covering Division I college baseball, which is an exciting level of baseball to observe. Every year, we'll see guys who have the ability to get to the next level. We all know that the MLB draft has enough rounds to give a lot of players a chance to change their lives.
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It is so hard to predict how good a baseball player will be, as the levels in this game can be so far apart. Even those who dominate in college have a lower percentage chance of succeeding in the MLB than a college football player who is drafted high.
Let's go through some of the biggest draft mistakes relative to the superstars that could have been taken with that very pick.
12. Yankees Draft Brien Taylor, Pass on Manny Ramirez’s Sweet Swing
In 1991, the New York Yankees were looking to bolster their pitching staff. You'll remember that their championship seasons at the end of the decade featured Roger Clemens and Andy Pettitte. That wasn't even an inkling in '91, as they wanted to develop the next Dwight Gooden.
That's how highly they thought of Brien Taylor.
The only problem is that their focus on the mound had them pass up a big bat in Manny Ramirez, who would skyrocket in prominence later in the decade.
11. Astros Pass on Derek Jeter for College Star Phil Nevin
This entry is not to call Phil Nevin a complete bust. I think it's more of a criticism of the Astros' frugal nature than of Nevin's ability. Hall of Famer Hal Newhouser was a scout for Houston at the time and lobbied for them to take Derek Jeter.
The team was concerned that Jeter was going to ask for a signing bonus of $1 million or more for him to forgo his college scholarship. Nevin ended up floundering at the MLB level with the Astros and had to bounce around a bit before becoming a great player for the San Diego Padres.
10. Orioles Take Ben McDonald, Miss Frank Thomas’ Monster Bat
You'll find that pitching can be the position that's overvalued in lists like these, but it's really because great pitching can be so hard to find. Ben McDonald was a superstar in college, becoming a Golden Spikes winner at LSU and leading the United States to a gold medal in the 1988 Olympics. It seemed like a no-brainer to choose him.
Unfortunately, they didn't see the immense power that was eventually selected a handful of picks later. Frank Thomas was selected by the Chicago White Sox, and the rest is history.
9. Padres Pick Matt Bush #1, Let Justin Verlander Go to Detroit
There is something about staying local when scouting and making draft decisions. Sometimes, it works out marvelously. Other times, you end up ignoring talent thousands of miles away across the country.
Matt Bush was right there in San Diego, playing for Mission Bay High School, and was easy to scout for the Padres.
They went with a logical, simple decision. Meanwhile, Justin Verlander was making some noise out at Old Dominion University, becoming a top pitcher in the conference and garnering the second overall pick behind Bush and the Padres.
8. Pirates Choose Daniel Moskos, Leave Madison Bumgarner on the Board
We could have gone with a number of teams in the 2007 MLB Draft, as Madison Bumgarner was picked 10th overall. We just went with the highest-drafted pitcher who didn't pan out. The Pirates picking Daniel Moskos fourth overall was almost a reaction to David Price going first.
They were both left-handed pitchers with a lot of potential.
The problem is that Pittsburgh didn't consider Mad-Bum enough in that category, so the Giants gladly and wisely took advantage.
7. Royals Bet on Colt Griffin’s 100 MPH Heat—Miss Out on David Wright
Many teams missed out on David Wright as he had to wait for 37 other draftees to go before he got the call.
The Royals had a top-10 pick in Colt Griffin, whom they thought would be a shoo-in to succeed at the highest level. Instead, that star flamed out before it could even really begin. Meanwhile, Wright started a career-long relationship with the team that drafted him, the New York Mets.
6. Mets Pick Steve Chilcott First, Let Reggie Jackson Become Mr. October Elsewhere
From a pick where the Mets eventually benefited, we go to one where they got the short end of the stick. Unfortunately, this is one of the few true busts in MLB Draft history. Steve Chilcott was a promising catcher who the Mets thought could become one of the best in the league.
He didn't even get a chance to make his MLB debut. Injuries kept him from advancing in the minor leagues, and he eventually retired early at the age of 24. The saddest part for the Mets is that Reggie Jackson was selected with the next pick after Chilcott.
5. Marlins Draft Josh Booty, Pass on Roy Halladay’s Cooperstown Career
I know that there are many high school athletes who excel at more than one sport. For Josh Booty, he was so good at football as well as baseball that the Marlins gave him a $1.6 million signing bonus just to commit to baseball and not put on the pads.
That didn't last long, as he eventually left to pursue a pro football career, and the Marlins were left with nothing from their fifth overall pick in 1994. In hindsight, they had a Hall of Fame career waiting down the line in that same draft in Roy Halladay.
4. Cubs Take Hayden Simpson, Watch Christian Yelich Become an MVP
We return to a common example of a team having their focus tunneled on pitching and passing up a future everyday star. Hayden Simpson had a good amount of hype coming out of Southern Arkansas University, but never could find his footing once he made it to the minor leagues.
The Cubs saw that first-round pick get squandered, and Christian Yelich was selected a handful of picks later. Yelich would go on to win the National League MVP in 2018.
3. Twins Pick Adam Johnson, Chase Utley Goes to Philly
Once again, pitching is such a roll of the dice because you never know these days, with the amount of injuries, surgeries, and just general hitting adjustments. That being said, front offices aren't exactly looking for a franchise player at second base.
This unique situation came to be when the Twins tried to bolster their future rotation with a second overall pick of Adam Johnson. Instead, Chase Utley rose to fame out of that draft as an indispensable member of the Philadelphia Phillies.
2. Reds Roll the Dice on Chris Gruler, Miss Cole Hamels’ Big League Brilliance
This entry is interesting because it compares a right-handed pitcher with a left-handed one. For Chris Gruler, we never really got to see his full potential, as injuries derailed his career before it could get going.
In my opinion, being able to find a potential southpaw ace is more unique and better to build around than a right-handed one. Cole Hamels supports that theory, as he created a deadly one-two punch with another guy on this list, Roy Halladay.
1. A’s Take Ariel Prieto, Watch Todd Helton’s Rockies Legend Begin
International talent has grown exponentially in numbers over the years, and the knowledge base of those players has had to grow with it. In 1995, the Oakland A's thought they had a future Moneyball superstar in Ariel Prieto, but future Hall of Famer Todd Helton was waiting in the wings and was picked a little later.
Call me crazy, but I think Helton would have been a perfect replacement for the eventual departure of Jason Giambi, because I think he would have stayed loyal longer than others at the time.
