Kyle Dubas cannot let Morgan Rielly just walk away with nothing in return, the way he has done with winger Zach Hyman and others.

As the Maple Leafs’ 2021 season unfolded, there was a growing sense among team-watchers that – barring some stand-on-his-head stretch of excellent performances – goaltender Frederik Andersen was playing in his final season with the franchise.

Andersen had too many bad memories clinging to his reputation with Toronto, too many letdowns stuck in the memories of Leafs’ fans, too many soft goals at the wrong time, too few games in which he’d stolen a win from the opposition. It didn’t matter that backup Jack Campbell played well enough to steal the starter’s job from Andersen – even if Campbell struggled and Andersen returned from injury to resume his role as the Leafs’ No. 1 netminder, Andersen would’ve had to thrive, and in short order, for him to wipe the slate clean and re-establish himself as Toronto’s starter in time to secure a big payday from the Leafs when he became an unrestricted free agent this summer.

That didn’t happen, obviously, and Andersen showed his character when he accepted a drastically reduced role with the Buds. But as the team headed into the off-season, it was all but publicly acknowledged by GM Kyle Dubas and the rest of Leafs’ management it would be moving in a different direction. Andersen’s salary cap hit of $5-million was far too rich for a club squeezed by a flat salary cap, and that, coupled with his sub-par play (including a regular-season save percentage of .895), spelled the end of Andersen in Toronto.

There’s another, current and longtime Maple Leaf whose career appears to be following the same trajectory as Andersen: defenseman Morgan Rielly

Now, Rielly hasn’t been underwhelming in the same way Andersen was in his final season as a Leaf. Indeed, Buds’ head coach Sheldon Keefe utilized Rielly more than any other Toronto skater, putting him on the ice for an average of 23:36. Rielly also chipped in five goals and 35 points in 55 games, which put him eighth among all NHL defensemen in points last season. The 27-year-old can still be a workhorse, and likely will be through the next handful of years.

However – and this is where his career trajectory with Andersen begins lining up – Rielly has never been part of a playoff winner in Toronto. This is not to suggest the Leafs’ post-season struggles are entirely his fault. But the stench of losing, and losing in horrible ways the way Toronto has, leaves a long-term mark on all players involved. Moreover, the fact Rielly will be a UFA at the end of the 2021-22 campaign, is likely to force Dubas’ hand: either get him signed to a contract extension, or trade him, either this summer or during the regular season. Dubas cannot let Rielly just walk away with nothing in return, the way he has done with winger Zach Hyman and others. He must make him fit under Toronto’s tight cap constraints, or move him.

But how in the name of Tim Horton can Dubas figure out how to retain Rielly’s services beyond this coming year? The Leafs’ reliance on their Big Four forward core (Auston Matthews, John Tavares, Mitch Marner and William Nylander), in addition to their financial commitments to D-men T.J. Brodie, Jake Muzzin, and Justin Holl, add up to some $53.15 million in cap space, used on just seven players. That would leave approximately $28-million to fill out the rest of their lineup, and some of that money will necessarily go to Campbell, should he replicate the success of his 2021 season.

With that in mind, riddle me this: how will the Leafs be able to match an offer like the one veteran blueliner Dougie Hamilton got from New Jersey ($9 million a year for seven years) for Morgan Rielly? How can Toronto slide a contract across the table at him that is less than the one Seth Jones just signed with the Chicago Blackhawks ($9.5 million per season for eight years)? How can they afford to put up as many dollars as the Columbus Blue Jackets recently did to extend the contract of D-man Zach Werenski (six years at an average annual value of $9.58 million)? It’s true, Werenski is three years younger than Rielly, but Hamilton is the same age as Rielly, and Jones is just one year younger. The market essentially has been set for elite defensemen, and it doesn’t make for encouraging news for the Leafs and their relationship with their top D-man.

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The Maple Leafs have been working diligently to develop Grade-A defensemen, and perhaps one of them – Rasmus Sandin, Travis Dermott and Timothy Liligren – can make the competitive leap, earn a large chunk of ice time, and make Rielly a surplus asset they can deal away to help plug lineup holes. More likely, at least for the time being, is that Keefe leans harder on veterans Muzzin, Brodie and Holl, and eases the youngsters into more meaningful minutes as the season progresses. But at some point, there will be a reckoning for Rielly and the Buds, and there’s no doubt it could end in a way Leafs fans will not enjoy.

Dubas came out during this current off-season and pledged his total support for the Leafs’ core of talent. He’d likely tell you Rielly is a part of that core, but that wouldn’t be entirely true. All of Toronto’s top four forwards are signed well-beyond the 2021-22 season, and thus would be easier in some facets to trade should the Leafs falter again in the playoffs.

Rielly, however, is a different asset altogether. Toronto brass has to make a decision on Rielly prior to the trade deadline, and it’s either going to result in major cap headaches next summer, or Rielly will be moved. There’s no way the Leafs can replace the steady, if unspectacular showings Rielly is famous for, but there’s also no way they can afford to throw massive amounts of cash to him.

Of course, things can change between now and the next trade deadline, and Dubas may yet figure out a way to hold onto Rielly for the long term. At the moment, though, it appears Rielly is headed toward a career crossroads. He can accept less money to try being part of the solution in Toronto, or he can let the UFA market decide where he winds up playing.

The decision he makes, and his play on the ice, will dictate whether he remains in Blue & White, or spends the latter portion of his NHL career wearing a different jersey.