Lowry only has one or two elite years left, which I think coincides pretty closely with his contract. If he is going to continue playing like a top twenty player, you gotta keep him. I have no problem riding this out.
For sure he can keep it up for a couple years. But if Leonard re-signs, does he really want to be in the middle of a five-year contract, in his prime, with a 34-going on 35 year-old PG with 14, 15 years in the league?
I think Lowry is playing stellar, but looking long term, who on the roster can inevitably take over for him at that juncture when he'll clearly slow down? (it's not like Lebron or a big SF that can slide to an undersized PF -- Lowry is a PG, plain and simple.) Van Fleet? Maybe, but he's up for an extension this summer, isn't he? Gonna have to pay the kid top dollar (which may be tough if you are going to give Leonard 190 million) to be a backup for a few years.
Just some stuff to think about. It's clear they are going to ride Lowry this year, and they should. But you're going to have to figure out how to reduce the age of that roster in order to realistically sign Leonard to a max deal. Danny Green is 31, and is more of a role player than a starter (even though he starts). You've got an old backcourt, and that really needs to be addressed (if I were Leonard's agent).
I am rooting for the Raptors. I hope they win the title this year, as I really think that fan base, and those players deserve it. But your GM, whose name I can't remember how to spell has his work cut out for him to lock in Leonard long-term.
p.s. Pistons had to win that game last night. Only fair, after the Raps axed Dwane Casey (which I think was the right move, but Casey is a dynamite coach). Was happy for him.
Oh, and p.p.s. Wolves now 2-0 in post-General Soreness era. They looked amazingly good in the first half, and then hung on to win it. KAT and Wigs look like they did before Butler came in, which is EXACTLY what I was hoping for. With Wigs now back at the 2 guard spot, and Covington playing SF and bombing away, it opens up things for WIgs to do his thing.