No. 2: Max Pacioretty
Pacioretty supposedly has a number of offers on the table right now and I'd be shocked if Toronto isn't one of them. Based on his age and recent injuries, the veteran winger will be an inexpensive option who teams hope can find lightning in a bottle.
It would be weird to see Pacioretty in a Leafs uniform, but I'd love to see it. Remember when Tomas Plekanec joined Toronto for the 2017-18 playoff run and how weird that looked? After spending 15 years with the Montreal Canadiens, he was all of a sudden a Leaf, but that trade worked out as he scored two goals and registered four points in seven playoff games versus Boston.
If Pacioretty was healthy over the past two years, he'd still be fetching $5M AAV on the open-market as team's would be lining up for his services, but the 35-year-old has a ton of question marks heading into this year. Although there are concerns about health, he seems like he could be an unbelievable pick-up for the Leafs this year.
He struggled in Washington last year, but he could be a force beside Auston Matthews or John Tavares. Toronto's core is going to draw so much attention that Pacioretty could be able to sneak into the open areas and return to that 30-goal player he was, just a few years ago.
Pacioretty shouldn't be asking for more than $1M AAV at this point in his career, so taking a flyer on him at that price should be a no-brainer. If it doesn't work out, they can easily flip his contract somewhere else or they can bury it in the minors like they always do. This is a classic low-risk, high-reward player that Brad Treliving should sign immediately.