He will be 28 at the start of next season. He will likely have 2-3 years on his next deal before age-driven regression starts. Players like Jake who get by on explosive speed tend to regress at a younger age than players who get by on high hockey IQ, physicality, all out effort, stickhandling, shot etc. Also, he is famously not a nutrition and workout fanatic, so that will likely accelerate his regression.
All this is to say nothing about his lack of drive and inconsistency etc.
Whomever signs him to his next contract is going to regret it, I just hope it isn’t the Bruins. Might as well trade him now. Won’t get much for him, but might as well get something.