The title sums it up. I don't think deals involving 8 players are likely midseason, but something like this would have to happen if the 76ers wanted LaVine without giving up Tobi.

For the Bulls, the motivation here is pretty simple. LaVine has value, but it seems to be decreasing given the size/length of his contract at his age combined with his recent play. Moving him and Caruso at once for a bunch of expiring contracts, at least two of which (Covington and Melton) could likely be flipped for even more assets isn't a bad idea if they decide to go full tear-down. I have them only getting two firsts here due to Lavine's decreased value, freeing up so much money, and getting more tradable assets back, but the exact value is less of a focus here than the players anyway.

For the 76ers, this would turn wing depth from a strength to a weakness immediately. For what it's worth, there were slightly easier deal constructions involving Batum instead of including Melton, House, and Drummond, but I thought the 76ers would try to keep at least one of the wings they got for Harden. After this trade, LaVine would present a massive offensive upgrade in the starting lineup over Melton, and should fit in nicely alongside Maxey, Batum, Harris, and Embiid. The bench would still be rather guard-heavy with Alex Caruso, Patrick Beverley, and Jaden Springer. Kelly Oubre would be basically the only good forward. However, getting Andre Drummond might allow the 76ers to shift Paul Reed to the PF position in some lineups if they need more size. Giving up two firsts is always tough, especially since this will entail a downgrade on defense (at least in the startign lineup), but the 76ers did just get these two from the Harden deal, so they might not mind giving them up again if they think the new firepower (and the ability to not play Maxey 39 minutes a night) might vault them into contender status.

I don't personally think the 76ers should go after LaVine in the first place. Caruso is a good smaller target, and other big defenders that can play off Maxey and Embiid better (like former Nick Nurse-coached guys in Pascal Siakam or OG Anunoby) are a cleaner fit. However, if they DID decide to go the Lavine/Caruso route, this is how they'd have to do it!