Before this gets turned down completely, think about this first. The Celtics are in a strange stage, they are on the very last legs of a legit title run. They are looking at a bleak future after this season, with only Rajon Rondo, Paul Pierce and Avery Bradley on the roster for sure, and maybe Jeff Green—but we will get to that.
The Celtics biggest problems come once the Big Three are off the floor. Jeff Green never looked comfortable in a backup role and had a hard time meshing with a veteran team. This could change with an offseason under his belt.
Danny Ainge recently said that it is not impossible for him to see Pierce coming off the bench next season. Danny might truly be in love with Jeff Green, but he doesn't fit for next year's push and he doesn't look like he can truly be a leader in the post-Big Three era. That means he needs to go. Teams will be all over Green to sign him. As a restricted free-agent, the Celtics can and should match any offer to keep him.
The Celtics, who would like to find a star of the future to play next to Rajon Rondo, would have found one in Derrick Williams. While Williams is under-sized for a power forward, he is quick enough to fit in at the small forward position. If Danny is serious about Pierce coming off the bench, Williams would be a huge offensive upgrade over Green.
So what would this look like?
The Celtics should flip Jeff Green, Ray Allen and the No. 25 pick in the draft for the No. 2 pick and Wayne Ellington. Why on Earth would David Kahn do this you are asking?
Well, first he's David Kahn. The man drafted three consecutive point guards IN THE SAME DRAFT and a player who basically told him he wouldn't play there no matter what. Then he picked up Darko Milicic, who he then compared to Chris Webber. Darko has performed admirably and has turned out to be a smarter move than we may have originally thought.
From Minnesota's perspective, this allows them to play small ball with Love, Green, Beasley, Allen and Flynn, who one would hope returns to form. Then Darko and Wes Johnson could come off the bench providing a solid top seven rotation.
So how does this help the Celtics?
The Celtics get more athletic and younger immediately. Losing Ray Allen hurts and Wayne Ellington is by no means a starting shooting guard, but he is able to shoot the three at a good clip at nearly 40 percent, which is only slightly lower than Ray and with more time, his attempts and makes would likely go up along with his scoring.
The Celtics need to add depth in the backcourt and that could be addressed through free agency. Wilson Chandler, Nick Young, Chris Douglas-Roberts and Marcus Thorton are all scorers who could help the Celtics long-term. This, combined with Derrick Williams and Rajon Rondo, would set the Celtics up to be competitive for the next five to seven years.
It's not for sure, but the Timberwolves are looking to get out of the No. 2 spot and the combination of Ray Allen and Jeff Green is probably better than what most teams are offering.
Does Danny have it in him to gamble on a draft pick? Probably not, but it sure would be fun to watch.