First of all, I refer you to the excellent article by Blake Murphy detailing the Raptors current and future salary situation. Blake also details possible and improbable trade options.
In my opinion, the biggest thing to focus on is the salary cap worksheet for next season. Currently, Gary Trent is looking for a contract similar to Tyler Herro, but Tyler is a slightly better shooter, and Gary is a slightly better defender. Tyler is a much better rebounder and passer, so I don't see Gary getting the 4 yr, 130 million that Tyler got, but somewhere in the range of 4 yr, 108 million (ie. 24, 26, 28, 30 million/yr). Fred, on the other hand, supposedly turned down a 4 yr, 114 million contract and rumor has it that he is looking at a contract along the line of Tyler Herro (27, 29, 31, 33 million/yr). Using the numbers above, puts the raps right up against the luxury tax line (approx. $161 million) with minimal cap space to fill out the roster (ie. more bench depth, center position, guard depth). In summary, signing both Gary and Fred to team friendly contracts puts the raps right against the luxury tax line and sacrifices any good options to help with bench depth. The Raps team would be similar to this year's team with less depth AND less options to improve the team. Raptors management is NOT going to go into the luxury tax for a borderline .500 team.
For the above reasons, most NBA teams feel the raptors will be doing a trade at the trade deadline. The Raptors have too many good young players (Barnes, Anunoby, Trent, Achiuwa, Koloko) to blow the team up and start from scratch. The following trade is more of a soft reset.
To Toronto Raptors:
Dyson Daniels, Jaxson Hayes, Devonte Graham, +/- First Round Pick, +/- Trey Murphy III
To New Orleans:
Fred VanVleet, J. Hermangomez, Malachi Flynn or Thad Young
For the Raps, the key to this trade is Dyson Daniels. He is young, excellent point of attack defender who fits vision 6-9 perfectly. Also, he is the type of player who doesn't need the ball in his hands to have a positive impact on the game. Hayes is a young big (who has had some legal troubles) who can provide the Raps with some young, experienced depth at center. Devonte becomes the veteran point guard (can shoot the 3 ball, but not as good a scorer, defender, or passer as Fred) until Daniels learns the position a bit more.
For the Pelicans, I equate this trade as similar to the Valanciunas-Gasol trade. We gave up a good, young player with potential, for a savvy veteran who can still play. Fred brings scoring, defense, passing, leadership and playoff experience/success to a young Pelicans team. The Pelicans are currently in 4th place (despite Zion and Brandon missing quite a bit of time) in the west with a higher seed being very possible. Assuming Zion and Brandon are able to play post All-Star break onwards, post trade, the Pelicans starting five would be:
VanVleet, McCollum, Ingram, Williamson, Valanciunas
with a bench of Alvarado, Temple/Murphy III, Jones, Nance Jr, W. Hermangomez.
Let me know what you think. Comments appreciated.