Over the summer, Danny Ainge and the Boston Celtics parted ways. After 18 years with the organization, Ainge believed it was time to move on. He and the Celtics have had great success throughout his time with the franchise.

They made the Conference Finals six times, NBA Finals twice, and took home one championship. Yes, they were expected to have more success over the years. However, for a team like the Celtics in this generation of the NBA, that resume is amazing.

In a previous article, we touched on the best moves he made during his tenure with the organization. However, it is time to look at the opposite end of the spectrum. Every GM, and/or President, has had their fair share of bad moves. Ainge’s moves are sometimes magnified, depending on the circumstance.

Nonetheless, Ainge has made quite a few questionable moves over the years. Here are the three worst.

3. Drafting Guerschon Yabusele

In the 2016 NBA draft, the Celtics had the No. 16 overall pick. They ended up drafting Guerschon Yabusele out of France. The pick was odd, but maybe Ainge saw something in the young forward.
Unfortunately, the big man never panned out.

He only lasted two seasons with the Celtics before being waived. No other teams in the NBA have called for his services since. The pick didn’t work, but that is the case sometimes.

The draft is a literal crapshoot. However, the Celtics have had issues with their supporting cast in recent years. The 2016 draft consisted of a good amount of players that can help the current Celtics team.

Malik Beasley and Caris LeVert are good young scoring guards in this league. Dejounte Murray is a good defensive guard with a lot of potential. Malcolm Brogdon won Rookie of the Year, while Pascal Siakam is an All-Star and champion.

All of these players were selected after Yabusele. A simple difference in that selection could have led to a Finals appearance and maybe a title in the rafters.

2. The Kendrick Perkins Trade

Kendrick Perkins is now known for being on ESPN handing out bold takes. Before all of that, he was a former big man enforcer for the Celtics in the late 2000s and early 2010s. His role was never scoring or being flashy.

His job was to be the rough and rugged post defender that can grab some rebounds. In addition to that, he was one of the leaders of that team. He was a no nonsense type of guy, but knew how to be a great team player.

However, during the 2011 NBA trade deadline, he was moved to the Oklahoma City Thunder for Jeff Green. On paper it was a good move. In reality, it was a move that hurt team morale and left a big hole in the roster.

The trade had some promise with Green’s talent. Unfortunately, he ended up having heart surgery and missed the entire season of their last chance of a title. This trade from Ainge was controversial and started that official era of the Celtics.

1. Trading Isaiah Thomas

Isaiah Thomas was on top of the world in 2017 with the Celtics. He made his second straight All-Star team and he finished second team All-NBA. Going from the last pick of the NBA Draft to All-NBA caliber was such a unique story.

Thomas was ready to be a Celtic for the rest of his career and sign a huge extension. However, that never materialized. Thomas ended up getting hurt with a severe hip injury that would sideline him for the beginning of the following season.

Instead of Ainge waiting for the guy who risked hurting himself even further, he wound up trading him to the Cleveland Cavaliers. The player they got in return was one of the best bright young stars in the league, and arguably better than Thomas at the time, Kyrie Irving.

As a franchise, that is a move you have to make. The ripple effects from this trade doomed the franchise, unfortunately. Irving lasted only two seasons and it did not end well either.

It has been a couple of years, but the fans have not forgotten his time in Boston. There was even an incident, last season, of a fan throwing a water bottle at Kyrie at the end of a game. Furthermore, this trade left a bad taste in several player’s mouths due to Ainge not showing Thomas loyalty.

Paul George and Kawhi Leonard refused to be traded there. Irving didn’t want to stay. Al Horford left. The Celtics wanted Anthony Davis for years, but was told by his dad that they were a dishonest franchise.

Several players and their inner circle were not afraid to voice their own opinions about how the Celtics operated.This trade has soured a lot of great players for ever wanting to play for the Celtics. The actual trade was a good move, but the aftermath has hurt the franchise for several years now.