With all the other retirements in the league is next year Teddy's last? He certainly has earned the right to stay as long as wants to. He has 20 years of being quite a good recruiter and an average talent developer. Whether it is he or the current assistants, I agree with the comments that talent development has lagged with the current upperclassmen.
Things will only get harder going forward in relying on recruiting as a the main driver of success with smaller rosters and all of the other changes like the portal and the potential to bring in folks from the Major Juniors. To succeed (at D1 as opposed to D2 or D3), Harvard will need the next coach to excel at both recruiting and development.
If Teddy stays, perhaps he should change up the staff a little so he can have better luck developing talent like some of the other ECAC schools. Alternatively, maybe he can have some influence to convince the ECAC and the Ivy League to get with the program enough to stay viable at D1. They don't have to go as far in hockey as in basketball to remain competitive but simply pretending it is 1989 in 2025 won't cut it.