He'll probably get none, unless a trade is made prior to that. Very hard to envision Ainge sacrificing next years cap space and flexibility to accommodate Olynyk, a player who may be gone next year if we go after a Max player as it is. Unless Ainge has plans to cut the fat somewhere else somehow or imagines he can move him easily.
Also, Olynyk is currently injured, so hard to commit to someone before he gets on the court and without probably much practice.
I know people were fond of being alarmists for Sullinger's health issues, but Olynyk's is equally concerning if not more so.
In all, it's doable, but I just don't see an extension happening. I'd wait and see for the Summer.
Pretty much this. They're not going to cut into future flexibility by much. Furthermore, if he signs an extension, his salary becomes more difficult to trade. Say he signed a 4-year, $40 million extension (which would be a bargain, by the way). His outgoing salary, which determines what the Celtics can take back, would remain its current $3.1 million. However, his incoming salary for the team receiving him would be the average of Olynyk's current salary and his new contract, and so would be about $8.6 million. It doesn't make him impossible to trade, but when players have disparate incoming and outgoing salaries, it makes salary matching a lot more difficult.
But the bigger deal is cap space. According to Eric Pincus, the max for a 7-9 year player currently projects to $28.3 million. Without any trades, if you assume that Zeller is gone (a safe assumption), but do account for 1st round draft holds, the Celtics have about $30-33 million in cap space (depending on how many of Young/Hunter/Mickey are kept, and where the Nets pick winds up), before accounting for Olynyk at all. Without a trade, there's simply not enough flexibility to extend Olynyk at this point, and depending how the numbers shake out next year, there might not be enough to keep him at all.