Keeping Leonard will always be the key to Toronto’s future. Aside from Davis and Giannis, there is no under-30 player I would rather build a team around.
If Toronto wins the East, I’m betting Kawhi signs a max deal, and Green sticks around for the same money, because no other team will make a big offer to a guy who has never put up big numbers.
I would keep Anunoby, Siakam and Ibaka, and see how the other guys react to being on a title contender.
Ibaka is only 29. If Horford is still effective at 32, they can extend Ibaka another three years.
My guess is that they can find a good, younger point guard through the draft or trade to replace Lowry for less than $33M in 2020, which means the core of Leonard, Ibaka, (good point guard TBD), Siakam, and Anunoby, would be intact until 2020, and possibly longer.
Once a team looks like they have a chance to win a title, there is always a flow of older veterans who will sacrifice money for a ring.