Here's a ridiculous one. This one started as a fake trade with my friend who is a Spurs fan. He wanted Jaylen Brown, and said he'd do Vassell, Castle, and the 2nd overall pick for him. The idea snowballed from there.
Celtics trade: Holiday, Brown, 25 28th pick, 25 32nd pick
Celtics receive: Vassell, Castle, Washington, and the 1st overall pick Flagg
The reasons are pretty evident for this trade. They get out of the 2nd apron. They refill their team with solid veterans and Flagg and Castle.
Spurs trade: Vassell, Castle, Johnson, 2nd overall pick
Spurs receive: Brown
According to my friend, he thought Brown was the best player for the Celtics in their championship run. He was excited about pairing Brown with Fox and Wemby and was hopeful about their ability to contend over the next few years.
Mavs trade: Washington, Thompson, Gafford, Marshall, Christie, Hardy, Prosper, Williams, Martin, Powell, 1st overall pick
Maves receive: Holliday and Durant, 25 28th pick, 25 32nd pick
The Mavs aren't trading the 1st overall pick, but if they were it would only be for a superstar player. I'm not as high on Durant anymore as many are, but he's been linked to them in the past. Their starting 5 is Davis-Lively-Durant-Holliday with Kyrie when he gets back. They fill out the roster with vet signings and the Celtics picks this year.
Suns trade: Durant
Suns receive: 25 2nd overall pick, Martin, Hardy, Marshall, Gafford, Thompson
The Suns get multiple solid veterans that can be flipped into other assets or used as they retool around Booker. The 2nd overall pick gives them a talent infusion.
Nets trade: nothing of consequence
Nets receive: Johnson, Williams, Prosper, Powell, Christie
The nets get multiple young players for participating in the trade.
Where to start? This trade is nuts on a lot of levels. Technically the numbers work, but the logic breaks down in several places. It went from the Celtics getting the 2nd pick to "how much would it take to flip that into the 1st pick?" to "wait the Mavs have been linked to Durant and Holliday in the past" to "the Nets need to be in this trade just to make it work."
Still, fun to think through as I tried to break the trade machine.