My ranking of the Top 10 Celtics trades:
Honorable Mention: The KG and Paul Pierce to Brooklyn Nets trade. I only put it here because so far all we have to show is James Young and Jaylen Brown. The fruits of this trade are obviously yet to play out, and could certainly vault into the Top 5 (or better) depending how things play out.
Honorable Mention #2: Kermit Washington, Don Chaney, and a 1st round pick in 1978 draft for Charlie Scott. The Celtics were in free fall from their 1976 title appearance. So Red acquired a player he always coveted in Kermit Washington. Unfortunately, Washington had been suspended for 60 days for sucker punching (and nearly killing) Rudy Tomjanovich. Scott's best days were behind him, and he would have limited impact for the Lakers, and would end his career in Denver. Chaney would play a contributing role as a defensive specialist for the 1981 title team.
Why is this trade listed here? The reason is that the Celtics would own the 6th (their own) and the 8th pick in the 1978 draft. With 2 picks in the top 10, Red was able to use the 8th pick to draft Freeman Williams, while using the 6th pick to draft an underclassman forward from Indiana State that would be a year away from playing.
10.) Tiny Archibald, Marvin Barnes, Billy Knight and two 2nd round picks for Washington, Kevin Kunnert, Sidney Wicks and Freeman Williams. Tiny would end up playing a key role in the 1981 title team. Best of all is that this trade would mark the beginning of the end of the infamous Wicks-Rowe era. And as for those 2nd round picks: one would be used to select an infielder for the Blue Jays.
9.) Charlie Scott for Paul Westphal. A trade that would have interesting ramifications, as the two players would meet later that season in the NBA Finals match between the Suns and Celtics. The young Westphal had trouble cracking the backcourt rotation that was anchored by JoJo White and Don Chaney. In a GFIN move, the Celtics decided to complement an aging roster (Havlicek was 35, Don Nelson 34, and Paul Silas 32) with the high-scoring backcourt player (24.8 ppg with the Suns). The move paid dividends as the Celtics were able to squeeze one more title out of the often overlooked Cowens/Havlicek/White era.
8.) Bailey Howell for Mel Counts. Howell helped the Celtics replace the retired Tommy Heinsohn during the final Russell years, and was a key playoff contributor to the 1968 and 1969 title teams.
7.) Bill Sharman for Chuck Share. Hall of Famer Sharman was a key contributor to the Celtics first few titles during the Russell era.
6.) Paul Silas for Charlie Scott. The young Celtics needed a rebounder, and they got a good one for their often overlooked 1974 and 1976 title teams. Upon completing an outstanding NCAA career at UNC, Scott decided to spurn the NBA join the Virginia Squires of the ABA. In a forward looking move, the Celtics end up drafting Scott in the 7th round, thereby retaining his rights in case he should decide to return to the NBA. By the time Scott had grown tired of the ABA, the Celtics had plenty of offense in the backcourt with JoJo White, so Scott was shipped to the Suns, where he would establish he could score in the NBA as well. Scott also gets a nod for being part of 3 memorable Celtics trades.
5.) There may be some recency bias here, but the IT4 trade certainly needs to land in the Top 5.
4.) DJ for Rick Robey. The early playoff exit in 1983 showed that the team had some serious issues in the backcourt. Tiny was at the end, and Buckner and Henderson were JAG's. Noone could believe all it took to acquire the 4-time All Star was a redundant backup center.
3.) KG trade. I put it up here, as while it wasn't as lopsided as some of the others, it made the team relevant among the local fan base again. It also gave Paul Pierce a well-deserved NBA crown.
2.) McHale and Parish for JBC and Rickey Brown. Even with Bird, it would have been a long way to a title without the 2 big guys in the middle.
1.) Bill Russell trade. The difference between possibly 2 or 3 titles and 11.
Toughest omission: The Ray Allen trade, which really belongs in the Top 10.