Sure, it's easy to look back on any given draft and see the guys below your team's spot who turned out better (and that's exactly what I'm going to do here).
But there are certain picks that really stand out as major mistakes that have hurt a franchise.
There is the drafting of Tony Manderich second overall in 1989 in front of future or current Hall of Fame players Barry Sanders, Derrick Thomas, and Deion Sanders. And then there is practically any draft day move made by either Al Davis or Matt Millen.
And certainly other factors like injuries, lack of surrounding talent, poor coaching, or poor fit for the team can contribute to the washout of an otherwise talented player.
You only need to look at the top five overall picks from the last few drafts to see that talent alone won't get you too far as a pro. Drafting that high and whiffing can set a franchise back considerably. The Lions, Browns, and Bengals have perpetually picked at the top of the draft, which tells you something about their success there.
But speaking strictly as a Vikings fan, the drafting of Demetrius Underwood in 1999 was a move that hurt when it could have helped.
It's commonplace nowadays to see young men, with all the measurables and athletic talent on loan from God, become instant millionaires by getting drafted.
Rarely do you get the combination of a lack of college production coupled with a first round gamble like in Underwood's case.
And on top of that, Underwood also has the distinction of having not played his senior season by his own choice. He seemed to have shown his college coaches other behavior that concerned them of his readiness to mentally make it as a pro, and they warned Minnesota scouts of their concerns.
Of course, Underwood could have overcome all of this and worked hard to become a good NFL player and helped the Vikings stay on top of the league. But he never made it through training camp, let alone play a single down for the Vikings, and they had nothing to show for his pick but the large part of a $5.3 million deficit from his contract.
Coming off of one of the most impressive regular seasons in league history, the Vikings were picking at the bottom of the draft. Having traded QB Brad Johnson to the Redskins for the 11th overall pick, they were poised to remain a league powerhouse and take the next step to the Super Bowl.
Using the Redskins pick for the QB of the future, Daunte Culpepper, let them concentrate on the defensive side of the ball, which was quite good in 1998, but aging in some key areas.
Stalwart defensive tackle, and team leader, Jon Randle was 32 years old (and playing DE mostly that season), run stuffing Jerry Ball was 35, and pass rushing end Chris Doleman was 38. The concept of building from the line back was under use, as the team had, three years earlier, drafted California DE Duane Clemons in the first and Vanderbilt DT James Manly early in the second.
Then in 1997 they used a first on LB Dwayne Rudd of Alabama. Clearly, the defense was the main focus on draft day for Dennis Green at the time.
So, when you see that the 29th pick in 1999 was basically a forfeit because of Underwood's mental instability, the easy question is, who should they have picked instead? The answer to that question is, of course, anybody.
The next two picks were DE Patrick Kerney to the Falcons and LB Al Wilson to the Broncos. Dre Bly and Mike McKenzie were two CBs taken later in the draft that would have helped on the defensive side as well.
But, when a young man has mental problems ,and his college coaches warn you not to draft him, Jim Finn (Mr. Irrelevent that year), or picking no one at all would have done less damage to the team.
The Vikings went on to record a nice season despite the odd and disturbing training camp before Underwood's release. They finished 10-6 and won the Wild Card game against the Cowboys before getting outscored by the Greatest Show on Turf in St. Louis. And, their other first round pick went on to have a few good (and even great) seasons as an NFL QB.
But no Vikings fan will ever forget hearing the name "Demetrius Underwood" on draft day 1999 and saying aloud, "WHO?"