Best Missed Draft Picks in Sports History

Key Insights

• Tom Brady going 199th in the 2000 NFL draft is the most discussed missed draft pick in sports history, because every team that passed represents a franchise that could have built a dynasty and didn't
• Sam Bowie over Michael Jordan in 1984 is the clearest single-pick contrast in any draft in any sport, with the outcomes so divergent that the comparison became a permanent cautionary tale
• Mike Trout going 25th in the 2009 MLB draft is the most quietly devastating baseball draft miss, because every team drafting in the top 24 had a legitimate scouting operation and still missed a generational player

The NFL Draft Misses

Tom Brady at 199 (2000 NFL Draft)

Six rounds. 198 picks. Every team in the NFL with access to the same scouting reports, game film, and combine data. All of them passed on Tom Brady before New England selected him with the 199th pick.

Brady won seven Super Bowls and is the most decorated quarterback in NFL history. The specific haunting quality of this miss is the repetition: not one team passing once, but every team in the league passing six times each before New England made the selection that built their dynasty. The 198 picks before Brady represent 198 separate franchise decisions that went in the wrong direction.

The Michigan Wolverines were his college team. He had started for a major program. The film existed. The information was available. The miss is real and documented and the gap in outcomes is as clear as any draft comparison in any sport.

Ryan Leaf over Peyton Manning? No. Ryan Leaf Instead of Peyton Manning.

The 1998 NFL Draft produced the most discussed quarterback comparison in the sport's history, and the specific lesson it delivers is about certainty at the position.

The Indianapolis Colts took Manning first overall. The San Diego Chargers took Ryan Leaf second. Manning won two Super Bowls, is widely considered one of the five best quarterbacks in NFL history, and redefined how offenses were designed. Leaf's career ended with 14 touchdowns, 36 interceptions, and some of the most documented behavioral problems in NFL draft history.

The gap between the two careers is so complete that the comparison became the standard reference point for discussing how wrong a franchise can be about the most important position in football.

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The NBA Draft Misses

Sam Bowie over Michael Jordan (1984)

The cleanest contrast in any draft in any sport, and the miss that became the permanent cautionary tale for NBA front offices.

Portland took Bowie at number two. Jordan fell to Chicago at number three. The reasoning was defensible at the time: the Blazers had Clyde Drexler at shooting guard and needed a center, and Bowie was a promising player. The injuries that limited Bowie's career and Jordan's subsequent dominance made the miss look worse in retrospect than it appeared in the draft room.

The specific quality that makes this the standard draft miss story is the clarity of the contrast. Jordan at three is the best player ever. Bowie at two played 139 career games. The gap is absolute.

Greg Oden over Kevin Durant (2007)

The most painful modern NBA draft miss, and the one with the clearest documented outcome contrast.

Portland's decision to take Oden over Durant was defensible based on available information. Oden was an elite defensive presence at Ohio State and appeared to be a cornerstone center. Durant's offensive brilliance was visible but centers were still valued more highly than wings in most draft evaluation frameworks.

Oden played 105 career games due to knee injuries. Durant became one of the most prolific scorers in NBA history, won two championships, and was a legitimate MVP contender for over a decade. The miss cost Portland a championship window they've been trying to find ever since.

The 2003 Draft: Darko Milicic at Number Two

The Detroit Pistons had the number two pick in the 2003 draft and took Darko Milicic. Available at that point in the draft were Carmelo Anthony, Chris Bosh, and Dwyane Wade.

The specific context makes this miss particularly interesting: Detroit won the NBA championship in 2004 with essentially no contribution from Milicic. The Pistons were good enough to win without a superstar at two. The what-if asks how many championships a Detroit roster with Carmelo, Bosh, or Wade in addition to their existing core would have produced, and the answer is genuinely uncertain in an interesting way.

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The Baseball and Hockey Misses

Mike Trout at 25th (2009 MLB Draft)

The most quietly devastating baseball draft miss in recent history, and one that every team drafting in the top 24 is still answering questions about.

Trout went 25th overall to the Los Angeles Angels in 2009. He became the most dominant position player of his generation, winning three MVP awards and producing numbers that compare favorably to the best players in baseball history. Every organization that passed on him had legitimate scouting operations and professional evaluators who watched the same player.

The miss isn't as dramatic as Brady's because baseball drafts are more uncertain and development timelines are longer. But the gap between Trout and most of the players taken ahead of him is significant enough to make it one of the most discussed recent baseball draft misses.

NHL Late-Round Legend Misses

Hockey's draft miss tradition is dominated by late-round selections who became elite players, which produces a different category of miss from the NFL and NBA:

• Henrik Lundqvist was taken 205th overall in the 2000 draft and became one of the best goalies of his generation
• Pavel Datsyuk went 171st in the 1998 draft and became a two-time Stanley Cup champion and two-time Selke Trophy winner
• Both misses reflect the specific challenge of projecting European players in the late 1990s, when scouting infrastructure for international players was less developed

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The best missed draft picks in sports history share one quality: they were available to teams that had the same information the selecting team had, and passed anyway. That's what makes them haunting rather than just historical. Brady was there at 199. Jordan was there at three. Trout was there at 25. The information was the same. The conclusions were catastrophically different.

FAQ

What is the biggest missed draft pick in sports history?

Tom Brady going 199th is the most discussed for the volume of teams that passed. Sam Bowie over Jordan is the clearest single-pick contrast. Both are correct depending on whether you measure the miss by repetition or by outcome gap.

Did Portland regret the Sam Bowie pick immediately?

Not immediately, because Bowie played and Jordan hadn't yet established himself as historic. The regret accumulated over time as Jordan's career developed and Bowie's injuries mounted. By the late 1980s the comparison was already a cautionary tale.

Why did so many teams pass on Tom Brady?

The combination of his combine performance, his Michigan competition for playing time with Drew Henson, and the general undervaluation of quarterbacks who didn't dominate their college competitions all contributed. The miss also reflects the general difficulty of projecting NFL quarterbacks, where miss rates remain high even with modern analytics.

Is Mike Trout's draft position the biggest baseball miss in recent history?

For a player of his career quality, yes. The 24 picks before him represent 24 organizations that had information about a generational talent and evaluated him below their 25th selection. The specific organizations involved and their subsequent drafts make the context of each miss interesting to examine individually.

Are NHL late-round misses as significant as early-round NFL/NBA misses?

The late-round nature makes them different in type rather than in significance. Missing Lundqvist at 205 is a different kind of evaluation failure than missing Brady at 199 because the expected value of late picks is lower. The specific players who became elite from those positions are the exception, not the expectation. That said, the organizational impact of developing a Datsyuk or Lundqvist in the later rounds is genuine regardless of the draft position.

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