There were rumours about the Leafs going after players like Jakob Chychrun, Patrick Kane, and Timo Meier before they pulled off separate trades for Ryan O'Reilly/Noel Acciari as well as Jake McCabe/Sam Lafferty. Then, with the deadline still a few days away, the thought of adding an insurance goaltender became the next "big" thing to talk about.
Ilya Samsonov and Matt Murray haven't had the cleanest track record when it comes to their bill of health, so the idea wasn't too far-fetched. To begin the season, the Leafs were without both goaltenders for a short while as Erik Kallgren had to take the reins for a bit - including a bumpy western road trip.
At the time of these most recent rumours, Murray was sidelined with an ankle injury and because of the tight salary cap situation, many wondered if the Leafs would hold him out for cap purposes, much like the Tampa Bay Lightning or Vegas Golden Knights have done with some of their players in recent memory.
Jonathan Quick was a name that had just become available after his shock trade to the Columbus Blue Jackets and Weekes was one of many insiders who believed the Leafs should've given it a kick at the can and added Quick as an insurance policy. The thought process behind that was to have an experienced playoff goaltender in case another injury occurred, you'd want to be prepared and although Quick has fallen off, he is still a 2-time Stanley Cup champ and a Conn Smythe winner.
The Leafs balked at the idea as the trade deadline passed, largely because it wasn't needed in Kyle Dubas and Sheldon Keefe's minds. Also, with Joseph Woll already showing the ability to play very well at the NHL level, the Leafs currently employ 3 relatively good goaltenders.
He was recently called out for it on Twitter after a video was posted of Joseph Woll making an incredible save midway through a 1-1 game against the Wilkes-Barre/Scranton Penguins of the AHL. He responded back saying he had never once questioned Woll's abilities and affirming that he never said Woll was incapable of being the number #3 goaltender for the Leafs - just that adding an insurance goaltender for the playoff run should've been a priority.
As it stands today, the Leafs are healthy in goal and are rolling along nicely with Murray back and Samsonov playing extremely well. If the wheels fall off the tracks anytime in the near future or heading into the post-season, they know they have a reliable rookie goaltender waiting in the wings in Joseph Woll.