Toronto Maple Leafs: Signing O’Reilly Would Be a Massive Unforced Error

CHICAGO, ILLINOIS - FEBRUARY 19: Ryan O'Reilly #90 of the Toronto Maple Leafs takes the ice for the third period against the Chicago Blackhawks at United Center on February 19, 2023 in Chicago, Illinois. The Blackhawks defeated the Maple Leafs 5-3. (Photo by Stacy Revere/Getty Images)
CHICAGO, ILLINOIS - FEBRUARY 19: Ryan O'Reilly #90 of the Toronto Maple Leafs takes the ice for the third period against the Chicago Blackhawks at United Center on February 19, 2023 in Chicago, Illinois. The Blackhawks defeated the Maple Leafs 5-3. (Photo by Stacy Revere/Getty Images)

The Toronto Maple Leafs are said to be interested in bringing back Ryan O’Reilly.

Doing so would get the Brad Treliving Era off to a terrible start, and it would cost the Toronto Maple Leafs for years.

Because Ryan O’Reilly might just be the biggest name on the free-agent market, at least at his position (centre) and he’s going to get paid.

So unless he decides that he wants to give the Leafs a Marc Giordano/Jason Spezza style bonus, signing him is going to be a bad decision.

Toronto Maple Leafs and Ryan O’Reilly

Even though O’Rielly is popular and most Leafs fans probably want him to re-sign, signing him is going to a terrible move.

He will cost too much money, he won’t return any value for what he’s paid, and the contract will be guaranteed to age horribly.

Ryan O’Reilly is 32 and he hasn’t played an 82 game season since 2018-19, something he’s only done twice since 2015.

Three years ago he was close to a point-per-game player.  In the last two seasons, he has not been and is clearly declining.

In each of the last two playoff years, he’s been under a 50% Expected Goals player.

O’Reilly brings a lot to a team, but he is no longer a star and he isn’t going to suddenly start being a point-per-game player again.  In the NHL, if you aren’t a star, you aren’t worth paying.  That sucks, but that’s how the salary cap makes things work.  It is literally impossible for an older player who doesn’t have any upside to be worth his contract.

If that player happens to be a “name” who will get more than his skills would be worth, it’s even worse.

In the NHL, any time you pay a non-star money or term, you are taking a big risk. When the player is over 30 and has declined visibly and statistically, you aren’t even really taking a risk, you’re just setting your money on fire.

O’Reilly with the maximum amount of money retained was a worthwhile risk for Kyle Dubas and the Toronto Maple Leafs to make going into the playoffs.  But based on his overall play, his age and how he figures to continue to decline signing him to a long-term deal makes no sense.

Brad Treliving made some fairly bad long-term free-agent signings with the Flames. For instance, Blake Coleman is making $4.1 million for the next four seasons until he’s 35.  Nazem Kadri was 32 when Treliving signed him for almost $8 million. 

Both of those contracts are worse than any single move Kyle Dubas made during his whole tenure, but either would be preferable to something like Ryan O’Reilly for three years at $3 million, which I doubt he’d ever sign for.

The Toronto Maple Leafs should not be interested in signing Ryan O’Reilly for anything over $1 million dollars and a single year.  If he wants more, let another team make a mistake and you win twice.