Max Pacioretty is only the latest in a long line of former stars nearing the end of their careers to land with the Toronto Maple Leafs in hopes of a) prolonging their career and b) chasing a Stanley Cup.
How often has it worked out?
We found six from the recent past (Ryan O'Reilly wasn't at the end of his career when he joined the Leafs, so he's not included) and ranked them on just that: their effectiveness for the Leafs long after their best days were behind them. More often than not, the intangible stuff loomed larger than the on-ice contributions. Injuries were a frequent problem. A few made it work in just the right way -- until, that is, Father Time finally caught up with them.
Then-Leafs GM Lou Lamoriello flipped a second-round pick and a couple prospects to Montreal at the 2018 trade deadline for Plekanec. It was a high price to pay for a fourth-line centre pegged to line up behind Auston Matthews, Nazem Kadri and Tyler Bozak. Plekanec looked odd in a Leafs uniform after a career spent in Canadiens colours. His role was drastically reduced and he made little impact. In 17 regular-season games, Plekanec didn't score and registered only two assists.
Then Nazem Kadri ran down Tommy Wingels in Game 1 of the first round, got suspended and left a gaping hole at centre. His eventual 2C replacement was Plekanec, who played between Mitch Marner and Patrick Marleau for Games 4-7 of that series with the Bruins. Plekanec held his own. He even set up a Marner goal and added an empty-netter himself in a Game 6 win. And that was it. Plekanec returned to Montreal the following season, suited up in three games, and never played again in the NHL. His time with the Leafs felt like a blip in a long career: 1,071 games with Montreal, 24 with the Leafs. The price paid never did match the end result.
Thornton was 41 and coming off a 15-year run in San Jose when the Leafs signed him to a one-year deal, worth $700,000, for the pandemic-shortened 2020-21 season. At the time it felt like a worthwhile flier for a guy who was still chasing his first Stanley Cup. Thornton wasn't a star anymore, but he had been reasonably productive for the Sharks only two seasons earlier and he promised to bring good vibes and a dose of leadership to Toronto. Then-coach Sheldon Keefe was clearly intrigued: Thornton started training camp, and the season, on the left wing of Matthews and Marner. Though early results for the threesome were strong, Thornton got hurt almost immediately. He fractured a rib, missed a month and struggled when he returned.
Even with top-line opportunity, not to mention a spot on the No. 1 power-play unit, Thornton produced little offence and was eventually moved down the lineup. At one point Thornton, a former MVP and scoring champ, went 17 straight games without hitting the scoresheet and 27 straight without a goal. Thornton started the playoffs on the fourth line and was barely playing by the time that first-round series against Montreal was over. Foot speed, or lack thereof, finally caught up to him. It's worth noting Thornton was beloved by the Leafs' young stars. He played 34 games with Florida the following season and never again in the NHL after that.
Simmonds wasn't quite old when he came to play for his hometown team in 2021 at 32, but he also wasn't close to the player he had been in Philadelphia. The Leafs weren't expecting him to score like he did in those days, when Simmonds was perennially good for 20- and even 30-plus goals a season. What they hoped is that Simmonds, signed to a one-year deal worth $1.5 million, would inject some toughness, some spirit, some character into their team. Simmonds did just that in his regular debut: He fought Ben Chiarot and even scored in three straight games a few weeks later.
Like Thornton, Simmonds got hurt soon after -- breaking his left wrist -- and never really recovered. In 26 games after the injury, playing mostly on the third line, Simmonds produced two goals and two assists and was held to a single point (an assist) in the playoffs. The Leafs loved Simmonds' intangible qualities though and brought him back on a two-year deal. His role grew increasingly marginalized, to the point of not playing at all in five of seven playoff games in 2022. Simmonds got into 18 games the following season and never scored playing seven minutes a night.
The problem with Marleau was always the contract. Even though Marleau was 38, Lamoriello signed him to a three-year deal in 2017 with a cap hit of $6.25 million. Marleau wasn't bad in the first year; he scored 27 goals for the second year in a row, playing mostly on Kadri's left wing, and added a pair of multi-goal games in the playoffs. By year two, it was clear that the hands were starting to go (16 goals). Then-coach Mike Babcock was still a believer though, playing Marleau in a top-nine role all season, including in the playoffs where Marleau failed to score.
Needing the cap space, and unwilling to commit so much coin to a potential fourth liner, then-Leafs GM Kyle Dubas dumped Marleau's contract to Carolina in the summer of 2019. The cost was high: a first-round pick that became impact forward Seth Jarvis. Like Thornton and Simmonds, Marleau was a popular personality among his teammates, Marner and Matthews especially.
Giordano was a shrewd deadline pickup by the Leafs, plucked from Seattle for three draft picks (two seconds and a third). He wasn't quite Norris Trophy-level Mark Giordano, but he wasn't far off either, even at age 38. In his first playoffs with the Leafs, Giordano, another hometown guy, averaged over 20 minutes per game, fourth among the Leafs' crew on defence. Valuing both his play and leadership, the Leafs re-signed him for two years with a marginal cap hit of $800,000. The deal looked to be a bargain early on as Giordano continued to excel despite his age, gobbling down huge minutes, including a stint as the team's No. 1 defenceman, amid injuries on the back end.
Then the playoffs came and, suddenly, Giordano looked like what he was: the oldest skater in the league. The Leafs made the second round, but by that point, Giordano had become unplayable and indeed was barely playing. The final year of his contract was a difficult one for him on and off the ice. His father died unexpectedly in February 2024. Giordano also struggled with injuries and found himself out of the lineup at playoff time.
It's kind of funny looking back that Spezza, long a nemesis of the Leafs during his time with the Ottawa Senators, became one of the team's more popular players in the twilight of his NHL career. Like many of the players we're talking about here, Spezza signed with his hometown team to chase the Cup that still eluded him and did so for the NHL's minimum salary of $700,000.
Things started awkwardly when Babcock weirdly scratched Spezza in the season opener -- his first potential game playing in front of friends and family for the Leafs -- and for plenty more games after that. After Babcock was fired and replaced by Keefe, Spezza got his opportunity and never looked back. Though he garnered fewer than 11 minutes per game during that 2019-20 season, Spezza managed to produce 25 points in 58 games. Most impressive was how willingly he embraced a reduced role and managed to convert himself from top scorer to useful bottom-six forward, someone who was even counted on for FOGO responsibilities on the penalty kill. If there's a path for aging stars like Pacioretty to follow, it's this.
Spezza's spirited and entirely unexpected bout with Dean Kukan was among the few highlights for the Leafs in a 2020 play-in series loss to Columbus. Spezza delivered bargain results again the following season: 10 goals and 30 points in 54 games playing for the fewest dollars he could take. He then tied for third on the team with five points in a first-round loss to Tampa. Spezza remained productive as a 38-year-old playing for the minimum again in year three -- 12 goals and 25 points -- but by late in the season, signs of age began to show and his spot in the lineup was no longer secure. Spezza was scratched in Games 1 and 2 against the Lightning and played spare minutes after that. He retired that spring, joining the team in a managerial role.