Portland is rumored to be targeting TM3. I think this is a great fit because his contract and Deni's contract would add up to be less than the average max for this year and the next two years. That is a great pair of young wings to have as building blocks!
In this trade I have Portland getting TM3 and Kevon Looney for Jerami Grant, Rupert, and two future first round picks that are the better of Milwaukee's or Portland's. That means that in 2028 and 2030, New Orleans would have their own pick, plus whichever of those picks are closest to 1st overall.
While I do think this is heavy draft capital to give up for a non-all star in TM3, his combined fit, contract, and the ability to get off Jerami Grant's money are all too good to pass up. Grant's contract being the deciding factor in Portland adding on the 2030 pick.
New Orleans gets significant draft capital while not falling off a cliff in terms of current day talent. Jerami Grant is a quality starter that can help this season while they don't have their own FRP and they may even be able to trade him for draft capital by the time it reaches the last year of his deal when someone may want a start level player on an expiring contract.