The Toronto Maple Leafs roster is in tatters.

At one point on Sunday, it had just 18 healthy players. A fuller inventory offered a truly sad account of what's left.

Four prospects who had recently come up from the Toronto Marlies. A few minor-leaguers. A handful of veterans with expiring contracts who expect to be dealt by the NHL's trade deadline at 3 p.m. on Monday. Only a few young players of consequence: Morgan Rielly, Nazem Kadri and Jake Gardiner.

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No captain. No one with more than 308 games played – less than four seasons – as a Leaf. Not a single veteran with any history with the franchise (unless you count Leo Komarov, who has spent most of his 10 years with the organization playing overseas).

The Leafs will officially bottom out talent-on-the-roster-wise on Monday when GM Lou Lamoriello trades whoever else can garner a 2019 sixth-round pick. But the low point of the deconstruction likely came on Saturday afternoon, when underdog goaltender James Reimer was unceremoniously shipped to the San Jose Sharks for a fourth-round pick.

There were other pieces in the deal, but they were inconsequential. It was a trifling return for a goalie in the midst of a very solid season, one who had been hugely active in the community and who badly wanted to stay.

On a completely rational, detached level, moving Reimer made sense. He doesn't have a contract next season – negotiations toward one hadn't gone well – and the Leafs are moving everyone in that situation for whatever they can get of value.

This is the automaton GMing that the NHL's salary cap world demands of teams in the Leafs predicament. But that doesn't mean it doesn't sometimes hurt. Reimer was a first-on, last-off type at practice for almost a decade, a remarkable rags-to-riches story of a kid from the middle-of-nowhere Manitoba who started playing organized hockey at 12 years old and somehow became the starting goalie in one of the centres of the hockey universe.

He wasn't a Vezina Trophy-level goaltender, but every year, he cared more than anyone else on the roster – even this season, when it made little sense to care and diehard fans were actively rooting against the Leafs in hopes of a better draft pick.

Even coach Mike Babcock – who can be tough on goalies and demanding on everyone – was thoroughly impressed with Reimer. Both who he was and what he did on the ice.

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Few would have been surprised had Reimer signed for a significant hometown discount to backstop this mess of a team for another year of rebuilding. That's what made one media outlet report on Saturday that he was asking for an outlandish $6-million-a-season deal – quickly refuted by Reimer's agent on social media – so dubious.

It didn't fit.

"Not even close," said Ray Petkau, the agent.

Ultimately, it made sense for the Leafs to move Reimer, especially given he is likely to be available again in the summer. A fourth-round pick isn't much, but it's something – something the Leafs gain for giving up a player for 23 meaningless games. (Let's set the over-under on how many of those they'll win at five.)

Lamoriello will be making several more such deals on Monday. P.A. Parenteau is rumoured to have strong interest from the New York Islanders, his former team, where he has strong chemistry with John Tavares. Fellow unrestricted free agents Brad Boyes and Michael Grabner may fetch picks deep in some distant draft, and goaltender Jonathan Bernier has been scouted by teams of late.

The Leafs will also continue their considerable roster churn by sending a pile of players back and forth to the Marlies on Monday, preparing so that the best of their youngsters can legally still play in the AHL playoffs come April.

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So some of the future is on the way, likely including 19-year-old wunderkind William Nylander, who is overdue for his first taste of the NHL.

But most of the past is now long gone as part of the selloff. In almost every case, that's a very good thing considering how sordid the Leafs recent track record is. There wasn't much you would want to keep.

Reimer is the exception. And there remains the possibility he'll be back.

For a lot less than $6-million.

"It's sports. It's hockey," Reimer said not long after learning he had been dealt. "It's a forever-changing thing. Obviously, I had a lot of good years here.

"It's definitely a weird feeling to be going somewhere else. But the changes that were being made in Toronto, obviously they're building to do really neat things and be successful in the future."

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There's a reason Leaf fans called him Optimus Reim. There's a reason, too, that they'll be cheering for him in San Jose.

He deserves it.