The Biggest NBA Draft What Ifs

How different would the Association had looked if different decisions had been made?

2007 NBA Draft Portraits

Now that Anthony Bennett has been bought out, his status as the worst top pick in NBA history has been cemented. However, it’s not like Cleveland made the worst decision in choosing Bennett first overall. There wasn’t a ton of talent that year, as Grantland’s Zach Lowe explains:

It’s not as if Bennett’s 2013 draft class has blown the league away. Re-draft today, and it’s plausible — likely, actually — that Giannis Antetokounmpo and Rudy Gobert would be the top two picks in some order. They went at nos. 15 and 27, respectively. Cleveland lost value by reaching for Bennett at no. 1, but it wasn’t an insane pick at the time, and none of the reasonable alternatives are going to inspire ‘what if?’ stories for the next 30 years. This is not LaRue Martin over Bob McAdoo, Greg Oden over Kevin Durant, or Sam Bowie (at no. 2, of course) over the G.O.A.T.

When I read that, I began thinking of those “What if?” stories. Here are eight of them that stand out to me:

  1. What if the Portland Trailblazers chose Michael Jordan instead of Sam Bowie in 1984?

Possibly the biggest “What if?” in sports history, no one needs me to rehash it. Even NPR has done an examination on it. Portland already had Clyde Drexler and big men were still coveted at the time (Hakeem Olajuwon went first that year), so they went with a center. Rarely has such a decision been proven to be so wrong, particularly at the highest level when Jordan’s Chicago Bulls defeated Drexler and the Blazers for the 1992 championship. Although Drexler has always believed he was better than Jordan, no one agrees with him. Literally no one.

  1. What if the Detroit Pistons chose anyone — Carmelo Anthony, Chris Bosh, Dwyane Wade, David West, Josh Howard, even Chris Kaman, Mo Williams or Kyle Korver —instead of Darko Miličić in 2003?

Speaking of second picks, imagine if Joe Dumars had gotten this one right. He had already assembled the pieces of what would become a veteran championship team, so how deadly would the Pistons have been with a young star? Choosing Carmelo would probably have changed the dynamic and the chemistry, but how about Wade in place of Rip Hamilton or Bosh playing a stretch-4 alongside Rasheed and Ben Wallace? Darko appeared in a whole 34 games as a rookie, averaging less than five minutes per. He was a glorified seat filler, although he did spawn a great website. Replace him with almost anyone else from the Class of ’03 and the Pistons rule the East for a decade.

  1. What if Chris Webber and Anfernee “Penny” Hardaway aren’t traded for one another in 1993?

This one has multiple angles to it. Webber and Shaquille O’Neal in the frontcourt together in Orlando? Devastating. Meanwhile, over in Golden State, Tim Hardaway was injured for the entire year, so that would have allowed Penny to play alongside Chris Mullin, Billy Owens and Latrell Sprewell to create Run-TMC 2.0.

More than their roster fits, there is also each player’s journey and ultimate fate. Webber clashed with coach Don Nelson and was shipped to Washington where he played well, but not spectacularly before ultimately reaching his peak in Sacramento. Penny was electrifying the first few years alongside Shaq, even outplaying a rusty MJ en route to the 1995 NBA Finals before injuries derailed him. Maybe Webber stays in Orlando more than a year. Maybe Penny’s body doesn’t betray him. Or maybe all that mess would’ve happened anyway.

[Interesting side note: what if the Philadelphia 76ers hadn’t wasted the number two pick on all-time stiff Shawn Bradley and taken Hardaway (or Webber) or Jamal Mashburn or Vin Baker or Allan Houston?]

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  1. What if Portland had not selected LaRue Martin over Bob McAdoo and Julius Erving in 1972?

Portland needs a draft exorcism. Unlike some other choices, this one took time to realize. Martin was far from a project. He had shown he could play with the best in college, but when he became a pro, he just couldn’t put it together. The Blazers would choose Bill Walton two years later, so the possibility of a team comprised of Walton and Erving – two guys that battled for the title in 1977 – sounds like dream.

  1. What if the Boston Celtics won the 1997 lottery?

Tim Duncan is not walking through that door, fans. Rick Pitino left Kentucky to join the Boston Celtics on May 7, 1997. With two lottery picks and the second-worst record in the league, Boston was expecting to win the top pick and coaching Tim Duncan (along with money) lured Pitino away from the college game. Eleven days after agreeing to become Boston’s coach, Pitino watched as San Antonio won the lottery and the Celtics were stuck with the third and sixth picks. They used those to choose Chauncey Billups and Ron Mercer, respectively, both of whom were traded in two years. Tim Duncan, meanwhile, is still with the Spurs and has led them to five rings. While revisionist history has dictated that Duncan would have worked his magic in Boston, the Spurs’ incredible success has had a long line of contributors aside from Duncan – from Gregg Popovich and the front office all the way down to David Robinson. Even with Duncan, could Pitino’s style have succeeded in the NBA? Would Duncan’s quiet leadership have had such an impact with a different team in a rabid town such as Boston? Maybe not.

  1. What if Len Bias had lived?

Amazingly, the Boston Celtics, who had just completed one of the greatest seasons in history, going 40 – 1 at home and winning the title, had the second pick in the draft. They chose Bias. How good was Len Bias? Really, really good. There were arguments over who was the best player in the ACC – Bias or Jordan. Taking a player of Bias’s skill and athleticism and putting him on a team full of smart but aging players with a system and a culture in place could have prolonged the Celtics glory years by another decade or so.

  1. What if Kobe Bryant hadn’t dropped to 13th – and what if Charlotte had not traded him to the Los Angeles Lakers – in 1996?

I was only 16 at the time and was not writing anything except bad poetry to girls that found me repulsive so I can’t link to it, but I knew Kobe would be better than most of the members of the Class of ‘96. I had watched him play in person in high school and it was clear that there was just something about him, particularly during that time before every 11th grader with hops was projected as a lottery pick. I couldn’t believe he fell to 13th. Bust after bust after bust went ahead of him – Lorenzen Wright, Kerry Kittles, Samaki Walker, Erick Dampier. Hell, even Todd Fuller was chosen two spots ahead of him. Finally, after Charlotte took him, they traded him to the Lakers in exchange for Vlade Divac, laying the groundwork for a future dynasty. He struggled early in his career, but after five titles and almost two decades, it’s obvious every team in the league should have taken Kobe.

  1. What if Portland chose Kevin Durant instead of Greg Oden?

Poor Portland. A great beer city, a wonderful basketball town, a horrible place for NBA drafts. Much like Bowie in ’84, hindsight says that everyone but the Blazers front office knew the correct pick and that is not true in either case. Plenty of people thought Oden was the right choice, most notably ESPN’s Chad Ford. Even with Durant, Seattle had its team ripped away from it, so Oden clearly couldn’t have changed that, but maybe the eventual Oklahoma City front office keeps James Harden if Oden was constantly hurt. And Durant would’ve been magical in Portland, giving that franchise hope instead of heartbreak.


Christopher Pierznik is the author of eight books, including the brand new In Defense Of…, all of which can be purchased in paperback and Kindle. His work has appeared on XXL, Cuepoint, Business Insider, The Cauldron, and many more sites. He has been quoted on Buzzfeed and Deadspin. Subscribe to his monthly reading review newsletter or follow him on Facebook or Twitter.