Boston Celtics: Top 5 Heartbreaking Moments in Celtics History

1. Len Bias and Reggie Lewis – What could have been

Yes, the Celtics have suffered a number of different tragedies and heartbreaking moments throughout their 72 year history.

But this one hurt. A lot.

Many know the story behind former Northeastern standout Reggie Lewis and Maryland’s Len Bias, two of the most incredible talents the Celtics ever acquired that didn’t pan out the way they were supposed to.

While we have done a number of in-depth looks at the two, both here and here, it all boils down to how the Celtics could have not only dominated the 80’s, but potentially could have grown to govern the 90’s and early 2000’s as well.

Len Bias was one of the most incredible two-way talents the world had ever seen. His prowess on the basketball court was often compared to that of a bigger Michael Jordan, and his swagger on the court and ability to affect others with his confidence is what made him such a dangerous basketball player.

Sadly, his mentality to be the best and thrive in a league that was at his fingertips was clouded by one errant decision he made not 48 hours after he was drafted by Boston.

Bias passed away of a cocaine overdose, and the basketball world mourned the loss of what could have been one of the greatest to ever play the game.

"“When Bias’ same playground swagger became fashionable in the ’90s — thanks to the UNLV guys, the Fab Five, the post-dunk woofing, the baggy shorts, the trash-talking and so on — it seemed much more contrived, almost like the players were saying, “Hey, look at me!”, The Ringer’s Bill Simmons noted during his time with ESPN. “Nothing about Lenny Bias was contrived. He went out of his way to dunk on people. He grabbed rebounds and spat out an occasional “Arrrrrrggggggghhhh!” for show. He barked at his teammates, he barked at referees, he barked at opponents. He exhibited a refreshingly honest amount of passion and heart.”"

Reggie Lewis, on the other hand, was the complete opposite of Bias on the court, as well as off it. Lewis was a mellow kid who played his college hoop at Northeastern University, becoming the at the time leader in points scored with 2,708 in his Husky career.

Lewis was found dead on July 27th, 1993 while participating in an off-season practice at Brandeis University. He was warned by doctors he would be risking his life if he ever participated in basketball activities after his collapse during a playoff game in the previous season.

As the years have passed, Boston fans still suffer at the thought of what Reggie could have been, and the wonderful person they never quite became familiar with.