To be fair to Lou, no one thought for a second JT would come home at that time. I thought he'd be an Islander for life. So during Lou's time if no JT comes, the Leafs have more than enough for all 3 of 34, 29, 16 as well as accommodating Patty for his 3rd year.
Problem happened when JT went FA. That's when we had to get creative with cap and no longer offer 8-year deals to our ELC stars. Leafs saw a window to be very competitive down the middle for close to a decade and they took it. I'd do it too.
It's been beaten to death but if a player like JT comes to market you scoop him up right away and maneuver around cap after. Core was on board with JT coming along, poor JT didn't know how greedy these kids are though.
JT played his entire career being underpaid and didn't go for money until UFA. What a change in mentality from that generation to this current generation of players.