I could see Masai having a talk with Lowry about his future to see what is more important to him, Retiring as a Raptor, making as much money as possible, or hunting another championship at all cost. If he wants to go hunting for either the most money possible or the path of least resistance to another ring then you trade him right now. Even if they make the playoffs, they aren't a contender this year as currently constructed. ....like not even close. I think if they make it in they will be a bottom 4 team and likely get eliminated in the first round. With no elite scorer to rely on every night and no elite team defense to rely on, they are in treadmill land right now....and if this keeps snowballing much longer they could end up high in the lottery.
All this starting 5 needs is a legit young athletic shot blocking, rebounding C with a jumper that isn't totally broke to develop along with Pascal, FVV and OG. This is why I wanted someone like Oturu in the draft over Flynn. Especially now that it looks like Davis likely isn't going anywhere. He would have been a perfect fit with this roster. I know he isn't playing much in LA now that they have both Serge and Zubac, but how nice would a 21 year old, 6'10", 240 lb C with bounce fit in with this team? All he did was average 20 and 11 with 2.5 blocks in college last year as a the primary option for Minnesota...while shooting over 56% from the field, over 70% from the FT line and 36.5% from deep on almost 2 attempts per game. Flynn may develop into something, but this core needed someone like Oturu a heck of a lot more than they needed Flynn.
So, that being said what about the following:
Lowry, Baynes and McCaw
for
Batum, Beverly, Oturu
Batum is an expiring 29M dollar deal, but he is a solid 6'9, three and D wing who's shooting 43.5% from deep so far this season. Beverly is a solid defensive minded PG who plays hard and would fit right in with this team with his ability to make open 3's, and Oturu gives them a young C with solid size and quickness.
With FVV looking like an all-star so far this season, they can afford to trade Lowry if he is likely gone at the end of the season for nothing.