# What is the biggest what-if in NBA history?

> Knees, draft picks and one phone call from the league office. Every entry here rewrote a decade that never happened.

*By YPB Team · Published August 25, 2026 · https://youpick.best/ranking/what-is-the-biggest-what-if-in-nba-history*

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## Current results (no votes yet)

1. **Portland picks Sam Bowie** — score 1000/1000
   Portland took Bowie second in 1984 and Chicago got Jordan with the next pick.
2. **Yao Ming's early retirement** — score 763/1000
   The most globally significant centre of his era retired at 30 with a broken foot.
3. **Jordan's baseball detour** — score 680/1000
   Michael Jordan retired at his peak in 1993 and spent a season in minor-league baseball.
4. **Derrick Rose's 2012 knee** — score 624/1000
   The youngest MVP in league history tore his ACL in his first playoff game that spring.
5. **The 1985 frozen envelope** — score 560/1000
   New York won the first draft lottery and Patrick Ewing, and the conspiracy theory never died.
6. **Penny Hardaway's knees** — score 560/1000
   Orlando's other star broke down before the partnership with Shaquille O'Neal could pay off.
7. **Portland picks Greg Oden** — score 397/1000
   Portland took Oden first in 2007 ahead of Kevin Durant, then lost him to knee surgery.
8. **Bill Walton's feet** — score 397/1000
   A dominant Portland centre lost most of his prime to repeated foot fractures.
9. **The vetoed Chris Paul trade** — score 397/1000
   The league office blocked a 2011 trade that would have sent Paul to the Lakers.
10. **Grant Hill's ankle** — score 397/1000
   A player compared to Jordan played 47 games in his first four Orlando seasons.
11. **Brandon Roy's knees** — score 291/1000
   Portland's All-Star guard was out of the league at 27 with no cartilage left.
12. **Kawhi Leonard's 2017 ankle** — score 291/1000
   San Antonio led Golden State by 25 when Leonard landed on a defender's foot.
13. **The 1998 Bulls breakup** — score 162/1000
   Chicago dismantled a team that had just three-peated rather than run it back.
14. **Kevin Durant's 2019 Achilles** — score 162/1000
   Durant went down in Game 5 of the Finals and Golden State's run ended with him.
15. **Ralph Sampson's Twin Towers** — score 162/1000
   Houston's 7-foot-4 forward broke down two years after reaching the Finals.
16. **Shaq leaves Orlando** — score 162/1000
   Orlando lost a 24-year-old centre to Los Angeles in 1996, a year after reaching the Finals.

Tags: basketball, players, nba, all-time