Given that they have been labeled as a “championship-contender” over the last several NBA seasons, this season was definitely a disappointment for the Boston Celtics, but they did learn a lot about themselves. Not only did they learn that Jaylen Brown and Jayson Tatum are going to make up a terrific duo in this league for a while, but they learned that it was time for a change of scenery in the front-office. 

Since 2003, Danny Ainge had been working in the Celtics’ front-office, but after losing in the first-round this year, Boston made the move to move on from Ainge and they promoted head coach Brad Stevens to be their new general manager. After promoting Stevens, the Celtics then made a big move to trade Kemba Walker 

Boston traded Walker, the 16th pick in this year’s draft and a 2025 second-round pick in exchange to the Oklahoma City Thunder in exchange for Al Horford, Moses Brown and a 2023 second-round pick. Then, after trading Walker, the Celtics hired Nets assistant coach and former NBA wing Ime Udoka to be their next head coach. 

Now, the Boston Celtics have turned their attention to the future of this organization and are looking for ways to not only get the most out of their championship window, but build for the future as well. One of the biggest problems the Celtics had this year was that their second-unit and bench was horrible. 

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Finding ways to add more talent to their roster without giving up any key talents will be key for them this offseason, which is why Aaron Holiday could be a realistic trade option for them. Boston needs some more talent in their backcourt after trading away Kemba Walker and Holiday could really use a fresh start. 

With that said, let’s take a look at an offseason trade idea that would send Aaron Holiday to the Boston Celtics in exchange for a few bench players and a second-round pick.