Jaylen Brown, 2016
The pain increases here, as Boston Celtics superstar Jaylen Brown was selected just one pick after the Los Angeles Lakers instead selected Brandon Ingram. The pain is mitigated, of course, by the fact that Ingram was a valid pick who was ultimately traded for Anthony Davis.
While it's entirely possible that Brown, who played college basketball at the University of California, could've been traded, as well, one can't help but wonder what could've been.
Brown, 27, is a three-time All-Star and former All-NBA Second Team honoree. He's thus far helped the Celtics reach the NBA Finals on two different occasions, as well as the Conference Finals in a remarkable six different campaigns.
A proven postseason player whose regular season résumé doesn't do him justice, the former Pac-12 Freshman of the Year is one of the biggest What If? draft misses in Lakers history.
Imagining a scenario in which the Davis trade happens, but Brown is kept out of trade talks instead of Kyle Kuzma, the Lakers would likely be contending in 2024-25. A trio of Brown, Davis, and LeBron James would be among the best in the NBA, with the former thriving as a long-term franchise player.
Instead, Brown is teaming with Jayson Tatum on a Boston Celtics team that has dominated the Eastern Conference in recent years and doesn't seem to be slowing down.