1. Michael Olowokandi (1998-2003)
Here’s a list of every first overall pick between 1996 and 2000:
1996: Allen Iverson
1997: Tim Duncan
1998: Michael Olowokandi
1999: Elton Brand
2000: Kenyon Martin
In this very carefully chosen slice of NBA history, Olowokandi is flanked by two all-universe Hall of Famers in Iverson and Duncan, and two All-Stars in Brand and Martin. They’re like a late-70s rock band, with two household names on vocals and lead guitar and two beloved backups on bass and drums.
But then there’s the triangle player. Nobody is really sure why he’s here or what he’s even doing. But he’s impossible to ignore. Eventually, the constant “ding-ding-DING DING” begins to haunt your dreams and invade your conscious mind, chipping away at your sanity until your entire lived experience morphs into a single, maddening chorus of chimes.
It’s probably not quite that deep, but basketball statistics won’t do the disaster of Olowokandi’s Clippers tenure much justice. He was good for around 9 points and 9 boards but cost the team their most valuable asset in years. Whiffing on a number-one pick seriously hurts, and having him around for five whole years was like the maddening triangle player from earlier.
Olowokandi was definitely talented and probably could have become a 15-10 player had he taken NBA basketball a bit more seriously. But myriad contract disputes, his alleged status as uncoachable, and a wildly confusing free agency after his rookie deal muted any chance of that.
Side Note: Number-one pick historians will note that I unfairly picked a 5-year slice—1996 to 2000—that conveniently makes Olowokandi’s pick look like the worst thing since unsliced bread. Had I expanded the range by one year on each side, noted busts Joe Smith (who was a solid player but never an All-Star) and Kwame Brown (a generational flop) would have been included. I’ll refer you to Darrell Huff’s 1954 book “How to Lie with Statistics” for further reading.