Not Drafting Dragan Bender- 
Ainge has been looking for his diamond-in-the-rough European superstar for most of the time as general manager. Bender placed very high on a lot of mock drafts, so it wasn’t as if he was a complete nobody. In 2016, when the Celtics picked forward Jaylen Brown with the third pick, Brown wasn’t exactly a clear-cut choice. Ainge had been scouting Bender for most of the year and was very impressed by the big man’s long term potential. Ainge and company had also been scouting Kris Dunn heavily as well as Marquese Chriss. Ainge did pick Brown in the end, and it was a way better choice than Bender. Bender has underwhelmed from the very start and three years later has only averaged 5 points and 1 rebound per game.
Never signing Dwight Howard- 
Ainge has wanted to get Dwight Howard on the roster since the Big three were still on the team. As Kevin Garnett was reaching the latter stages of his career, Ainge felt Dwight was the perfect replacement. Every year since about 2011 or so, Ainge has always had in the back of his mind to sign or trade for the former Orlando center. One of the main reasons that Ainge was not able to get Dwight to the Celtics was due to Howard’s high asking price. In order to add Dwight’s large contract on the books, Ainge would have had to cut most of his better players. Between the years of 2011 and 2018, Howards yearly salary has increased annually while his numbers have decreased every single year in almost every category. Ainge would have ultimately needed to give Howard a long term 200 million dollar deal to lock him up, or trade away some of the Nets drafts picks which netted them Jaylen Brown and Jayson Tatum. Was Dwight Howard worth a 200 million dollar contract the last 5 years or two top draft picks?
Not Drafting Markelle Fultz- 
This is the biggest bomb avoidance on this list. Scouts and NBA GMs were rating Fultz higher and higher with every passing week during his freshman year at Washington. Fultz made third team All-American in his freshman season, but scouts felt he had the athletic skills and scoring abilities to go ahead of everyone else in the draft. Now, Ainge did feel that Fultz would be a great player, he just didn’t think that Fultz was leaps and bounds ahead of the rest of his draft class as other scouts saw it. Ainge did trade the pick with 76ers, and received another pick in that deal. Ainge went with Duke swingman Jayson Tatum, and he has performed at the very top of his draft class. Meanwhile, between Fultz’s injury, shooting mechanics disaster and confidence issues, he has averaged just 7 points per games in a very limited sample size. Philadelphia traded him this past year to Orlando for a former undrafted player and two second round picks. Can you remember a time when a number pick was worth two second rounders and an undrafted player just two years after being drafted?
Not trading for Carmelo Anthony- 
Lets get something out of the way: Carmelo Anthony deserves an NBA roster spot somewhere, just not in Boston. Its a sad story that Anthony is still not an NBA team, because he has the talent to help some team out with offense and veteran presence. Now, on from the that, Melo would have been a disaster fit with the Celtics. Brad Stevens runs a sort-of college style offense in which any player can get offensive opportunities. Stevens and Ainge have always preached positionless and unselfish basketball, and for a greater part of Steven’s tenure, has worked out pretty well. Now try and sell that to a veteran scorer like Carmelo Anthony. Celtics have always been mentioned in Carmelo Anthony rumors, and in the end Ainge never pulled the trigger on any of them. Ainge knew that Carmelo would have not fit into Stevens offensive philosophy.
Trading Jeff Green- 
Jeff Green had a strange four years in Boston. Boston originally traded for Green with the hopes of Green matching up well against the younger and more athletic Miami Heat. The one thing that the Celtics were missing at the time was athletic sparks off the bench and he had it. Once Boston moved on from the Big 3, Green was then moved into the team captain role with hopes that Green could move into Paul Pierce’s position. Green became the Celtics lead guy and averaged around 17 points per game. The Celtics had Green on a 9 million dollar a year contract, which wasn’t so bad considering that Green was putting up solid numbers. The Celtics realized that Green was never meant for the leader role or max contract and dealt him to the Memphis Grizzlies before having to extend a long contract his way. Danny Ainge knew that Green was a solid starter player, but not a part II to Paul Pierce or NBA All Star.
Picasso Baby 