This season, the Leafs have lost a player to waivers 5 times, though Adam Brooks accounts for two of them. That being said, it's odd that it happens to the Leafs more than anyone else.
When Brooks was waived by the Vegas Golden Knights, no teams except the Leafs put a claim on him - but when the Leafs waived him in hopes of stashing him in the AHL, the Jets claimed him. A move that was justified at the time, as Brooks being young and from Winnipeg, but perhaps it was Kevin Cheveldayoff getting one up on Kyle Dubas.
The Michael Amadio's of the world pass through waivers on a regular basis. Unfortunately for the Leafs, when they put him on waivers he was claimed by the Golden Knights. Granted, GM Kelly McCrimmon does need inexpensive NHL players due to his team's cap structure, but come on.. Michael Amadio?
Eleven players lost to waivers in 4 years seems a little lofty to be a coincidence. Dubas himself even called out his fellow GM's during his post trade deadline press conference, cracking a joke about how many players the Leafs have had claimed and telling agents to recommend Toronto as a stopgap destination to find them a guaranteed home.
I've gotta say.. I loved Kyle Dubas' newfound sarcasm and willingness to break GM kayfabe to call out some of the things he's seen unique to Toronto that we just don't see with other franchises.