As I was running through the NBA teams and their cap situation on shamsports capulator, one thing that stuck out was the similarity between the Bucks and the Pelicans roster and situation.
Obviously, this similarity starts with Davis and Giannis. They both play the same position. They score at extremely efficient rates. Giannis is a much better creator and passer. Davis is a better shooter and defender (not by much on defense). Both players are in their prime. Both players are MVP candidates. Both players are potential HOFers.
Next, there is a very close similarity between the second options. Middleton and Holliday both play the wing (Holliday is more of a guard, but both play off ball). Both guys are fringe all-stars. Both are really good scorers at all three levels (though not elite). Both can play good defense as well.
Then you have your supporting cast. Mirotic and Illyasova are similar players, but Mirotic is better. Moore is a similar player to Snell (I'd take Moore). Dellavadova is a similar grinder at a different position to Hill - both on bad contracts. Payton and Bledsoe are similar players (I'd take Payton).
I might be stretching it here, but both Henson and Randle are lefty bigs with limitations (I'd take Randle). The Bucks have Brogdon, Wilson, and Maker as interesting prospects, but I think only Wilson has the chance to be a starter on a high level team, and even that is dubious. The Pelicans have Diallo and Jackson as interesting prospects, and I don't think either are rotation players on a high level team.
Giannis = Davis
Middleton = Holliday
Bledsoe = Payton
Illyasova < Mirotic
Henson < Randle
Dellavadova = Hill
Snell = Moore
Brogdon > Jackson
Maker = Diallo
Wilson = Miller
Lopez > Ajinca
Neither the Pelicans nor the Bucks are in a good financial situation. Holliday forced the Pelicans' hand last year, demanding a huge contract, knowing that if the Pelly's didn't pony up, it would likely lead to Davis leaving. I think Middleton does the same thing this off-season with the Bucks. I could see Middleton commanding 30 million a year, not because he's worth it, but because he knows the Bucks have no other way to replace his production and Middleton leaving might lead to Giannis leaving.
Honestly, the Pelicans aren't in terrible financial shape, but unless they get a MLE guy (or minimum guy) that outplays his contract by a lot, they also have no real way to take the next step forward into contention. They don't have the assets to swing a trade for a high level guy.
The Bucks, however, are in a much worse financial situation due to Snell's, Dellavadova's, and Henson's poor contracts. By my count, without resigning (and with renouncing) Bledsoe and Brogdon next year, they will be over the cap and only 12 million dollars from the luxury tax line. Assuming they sign one of the two of them back to play point guard for them, they start rubbing against the luxury tax really quick.
I think there is enough hope and flexibility in New Orleans that the Pelicans can try to keep Davis for one more year. For the Bucks, if their young players continue to lack development, I could see Giannis realizing he has no chance to make it to the finals in Milwaukee. I think both players want to get traded before the end of their contracts.
Side point: I think both teams are possible trade partners with the Hornets for Batum.
As far as the Celtics go, I'd love either player normally, but I really like this team. I also wonder how in the world the Cs avoid a 9 figure luxury tax bill in 3-4 years without losing one of Kyrie-Hayward-Horford-Tatum-Brown. Also, there is no way they can pay the luxury tax bill if they trade for one of those guys without giving up one of their core.