Here are 3 instances where the Maple Leafs missed out on making a trade or signing a player that could have changed their franchise trajectory.
Wayne Gretzky
Gretzky was linked to the Leafs in 1996 off season when he was an unrestricted free agent. Things at the time had even progressed so far that GM Cliff Fletcher had an agreement in place with The Great One, but the Leafs Board of Directors shot it down due to financial reasons.
Eric Lindros
Lindros ultimately ended up a Leaf, but unfortunately it was long past his prime. It turns out in 2001 the Leafs had a deal worked out in principal to acquire Lindros. The package was agreed upon Danny Markov, Nik Antropov and a 1st round pick to Philly for Lindros.
But two days went by and Philly decided that wasn't enough and things soured quickly as can be seen in this video.
Vincent Lecavalier
There were two times Lecavalier was supposed to be a Leaf. Once to circumvent the compliance buyout window and once when he was 21. The deal was all but agreed upon with Nik Antropov and Tomas Kaberle to the Lightning for the 21-year-old former first-overall pick.
Unfortunately for the Leafs when the trade call was supposed to happen GM Rick Dudley got over ruled and the deal never ended up happening.
These are just 3 stories of players who were almost Maple Leafs.