Toronto's past interest in Arber Xhekaj and Sean Monahan shows that prior management knew their roster needed specific pieces that took until this summer to acquire.
Herb Zurkowsky of the Montreal Gazette reported that an unnamed source revealed there was prior interest two years ago from the Toronto Maple Leafs in Canadiens players Arber Xhekaj and Sean Monahan - who now plays for the Columbus Blue Jackets:
A source on Thursday told The Gazette that Toronto was interested in Arber Xhekaj and former Canadiens forward Sean Monahan two seasons ago. But the Maple Leafs have undergone a management change.
Monahan was traded in February 2024, so the timeframe lines up with the Maple Leafs' interest.
Xhekaj and Monahan fixed two weaknesses Toronto still talks about today
Xhekaj, 25, would have added a cheap left-handed defenceman who feasibly could have taken the same role as Simon Benoit did - a physically dominant, gritty, and tough as nails blueliner.
Monahan, 31, would have been a player that helped solidify the middle of the lineup and give Toronto their 3C they spent years trying to find. Monahan would have added secondary scoring, power-play and penalty killing help, and been able to help drive the offence more on the third line but could have easily swapped up and down the lineup depending on situation.
But looking back, acquiring one or both of those players would have solved a lot of weaknesses. Toronto would have had a reliable and consistent two-way centre in Monahan, who could take tough minutes off both Auston Matthews and John Tavares' plate, and Xhekaj could have added a lot of protection.
You have to wonder how the reaction to the Radko Gudas hit would have gone if Xhekaj was part of the team. He's a massive presence willing to fight anyone for the sake of his team, and we might not have had such discourse when it comes to the Maple Leafs' toughness.
If management knew two years ago that the team needed these improvements, then they at least at the foresight to target their weaknesses. There's no public indication of a package for either player, but there were clear needs then that weren't addressed until two years later.
John Chayka found those roles without acquiring either player however
Toronto didn't just add one defensively sound centre - they added three. Nick Paul, Colton Sissons, and Teddy Blueger will work by committee to help balance the lineup and give them that stability that Monahan would have offered but spread throughout the lineup.
All three players can play the wing, so they can swap out as necessary and though Paul had a down season in 2025-26, he has scored 20+ goals multiple times in his career, so there's the offensive part covered too - though is coming off a wrist injury so you can't depend on him to hit that plateau immediately.
On the backend, Toronto added Darren Raddysh and Emil Andrae which added more offence and mobility though doesn't quite offer the toughness and aggressiveness of Xhekaj and solve a different problem for the team - that being puck movement and mobility.
They did however add a similar player up front in Brandon Duhaime. He's recorded at least 140 hits per season over his career, is known to fight, provides a lot of energy and helps bring the crowd into the game, and will make life miserable for opponents - it's not on the blueline but it's on the ice nonetheless.
It's not like they don't have players who won't get involved as both Jake McCabe and Oliver Ekman-Larsson have no issues getting in the middle of things but they are not your physically dominant or aggressive type of players.
Though there's been a regime change and a lot of overhaul both in the front office and the on-ice product, the ghosts of the Maple Leafs' past weaknesses still haunt them and they're hoping adding multiple pieces to cover Monahan and bringing in the toughness like Xhekaj is the solution - even if they never acquired them.
Do you think Toronto would have been better off with Sean Monahan and Arber Xhekaj?
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