They had Matthews and Marner on ELCs in 18-19. They had to take a swing at that. Then Tavares had his best season that year. Then they were up 3-2 on Boston. That was the year to do it.
Chicago did it early. Pittsburgh did it early. Edmonton tried to. At least some of the guys the team was built around still on ELCs.
They still had Kadri. They still had Hyman. They brought in Muzzin.
That they didn't get the job done, when they took that shot, yeah. Chicago had to re-tool a bit after 2010. Pittsburgh missed a lot of chances after 2009. The Leafs didn't get it done, but you can't fault them for trying to take advantage of those big name ELCs. I don't know who else was realistically out there to get in 2018, but in a hard cap world, with 2 star players on ELCs? Any team in that position that could've signed Tavares at that time, does. No question about it.
Spending on vets is one thing. Spending on a vet they didn't need is something else.
Toronto was 4th in the league in scoring in 2017-18. In 2018-19, Tavares had the best year of his career and Toronto finished...4th in scoring. They finished 3rd, 6th, 2nd, 9th and 2nd in the years since.
They were 12th in goals against in 2017-18. in 2018-19, they were 20th. In the years since, they were 26th, 8th, 20th, 6th and 21st.
The Tavares contract has kept them from properly addressing issues on defense and in goal. They had a couple years where they were top 10 in goals against but couldn't maintain that level of play due to cap issues and inconsistent goaltending.