The Toronto Maple Leafs made it official on Friday, naming Kyle Dubas as Lou Lamoriello’s replacement as general manager. It’s a major leap of faith by the team, with the fate of the 101-year-old franchise now in the hands of a GM who’s just 32 years old.

We can’t pass a final judgement on the Dubas era quite yet — we’ll give him about one more week before we get started on that. But in the meantime, we can see how the other men to hold the job stack up with each other.

We’ll be looking at all of the full-time GMs in Maple Leafs history — we won’t count any interim tags, or the time that the team went without an official GM for a little over a year. That leaves us with 16 pre-Dubas GMs to work with, which seems like a good number for a ranking. Let’s count them down from worst to best, starting with the least-effective Leafs’ GM of all-time. As you might expect, there was some decent competition for that particular honour.

No. 16: Howie Meeker (1957)

Record: Not applicable.

Signature move: None.

There could be some debate over whether Meeker even deserves a spot on this list; after all, he didn’t even make it to his first game as Maple Leafs’ GM before he was “reassigned” to the PR department. But he did officially hold the role, however briefly, so we’ll include him.

Meeker had had a distinguished career in Toronto, including winning the Calder in 1947 and spending a season behind the bench in 1956–57. That year hadn’t gone that well, with the Maple Leafs missing the playoffs, and Meeker was bumped upstairs to the GM job once the season ended. But it didn’t last, and Meeker was out of the role before opening night. News reports of the day called it a resignation, but Stafford Smythe left little doubt as to what was really going on, telling reporters that “[Meeker] didn’t have the experience needed in that kind of job and we didn’t have the time to let him gain that kind of experience.”

The Leafs didn’t formally fill the GM’s role until over a year later, going with a committee approach (although Smythe was rumoured to be calling most of the shots).

No. 15: Floyd Smith (1989–1991)

Record: 61-84-5

Signature move: Trading a first-round pick for Tom Kurvers.

The Leafs finished .500 in Smith’s debut season, the first time that happened since 1978–79. But his second year was a disaster, one that saw an aging Leafs team start 1-9-1 and very nearly finish dead last. They rallied to finish ahead of the Nordiques, meaning the Kurvers trade cost them Scott Niedermayer instead of Eric Lindros, and Smith was fired after two years on the job.

To give you a sense of how the Smith era played out in Toronto, here’s local sportscaster Joe Tilley not mincing words.

No. 14: Hap Day (1955–1957)

Record: 45-67-28

Signature move: None stand out; the few Leafs traded during this time basically amounted to selling fringe players for cash.

There’s some confusion as to whether Day ever officially held the GM’s title, but everyone seems to agree that he was running the show at the end of the Conn Smythe era, so we’ll include him. The team made one playoff appearance in Day’s two seasons, but after missing in 1957 he was publicly criticized by the Smythe family and forced out, ending a Maple Leafs career that saw him win seven Stanley Cups as a player and coach.

No. 13: Gord Stellick (1988–1989)

Record: 28-46-6

Signature move: Trading Russ Courtnall for John Kordic, which to this day I insist was a good trade. Note: I am the only person on Earth who thinks this.

At just 30 years old when he took the job, Stellick was the youngest GM in history; he was even younger than Dubas is today (although his league-wide record has since been broken by 26-year-old John Chayka in Arizona).

Other than the Kordic trade, Stellick is best remembered for the draft where the Leafs had three first-round picks and used them all on Belleville Bulls. None of those selections worked out, but people forget that the Leafs had all those picks because Stellick was somehow able to get two firsts from the Flyers for veteran goalie Ken Wregget at the deadline.

Stellick was fired that summer, and went on to join the Rangers’ front office before heading into a career in the media.

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No. 12: Dave Nonis (2013–2015)

Record: 94-97-21

Signature move: Signing David Clarkson to one of the worst contracts in league history.

Nonis was the GM for the team’s first playoff appearance of the salary-cap era, although he did it with a roster largely built by Brian Burke. Then came the disastrous Game 7 meltdown against the Bruins that seemed to send Nonis and the Leafs into panic mode. They threw a massive, buyout-proof contract at Clarkson, traded for Jonathan Bernier and one year of Dave Bolland, and doubled down on fourth-line toughness even as the rest of the league was moving on from it. The team cratered, Brendan Shanahan arrived, and soon Nonis was gone.

Maybe the best thing that could be said about the Nonis era is that by guiding the team towards rock bottom, he finally paved the way for the long-awaited rebuild that’s paying off today.

No. 11: John Ferguson Jr. (2003–2008)

Record: 145-110-10-30

Signature move: Trading a young Tuukka Rask for Andrew Raycroft.

Ferguson may be the most-maligned GM in Leafs history, and there’s a good chance you were expecting to see him much earlier on this list. There’s no denying that he made some disastrous moves; not only did he deal Rask for Raycroft, but he tried to clean up that mistake by spending multiple picks on Vesa Toskala. Mix in his decision to go old and slow coming out of the lockout and his penchant for handing out the no-trade clauses that torpedoed the 2008 deadline, and it’s clear that his tenure represented a major step back for a team that was a legitimate Cup contender when he arrived.

So how does he nearly crack the top 10? A few reasons. First, he somehow has the second-best winning percentage in Leafs’ history, which is incredibly depressing. And second, there’s some question as to how much of the Leafs’ post-lockout mess was his fault. One version of the story is that Ferguson wanted to do the sort of full-teardown rebuild project that Shanahan would start a decade later, but was denied permission by ownership. We may never know how much of that is true and how much is just sympathetic retconning of the facts, and ultimately the buck stops with the GM. But while Ferguson failed, it’s possible that nobody could have done much better under the circumstances he was up against.

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No. 10: Gerry McNamara (1981–1988)

Record: 166-302-67

Signature move: Drafting Wendel Clark first overall in 1985.

Poor Gerry McNamara. He’s remembered as the GM of the worst era in Leafs’ history, as the 1980s saw the team go from also-ran to outright joke. He boasts the worst record of any Leafs GM, and even the addition of the beloved Clark only came because the team finished dead last.

On the other hand, well, McNamara’s boss was Harold Ballard, and vintage Sam Pollock wasn’t going to win anything with Ballard looking over his shoulder. If anything, the fact that McNamara lasted almost seven seasons without strangling anyone or being forced to wear a paper bag over his head probably counts as a victory.

No. 9: Ken Dryden (1997–1999)

Record: 75-73-16

Signature move: Signing free agent Curtis Joseph after a late-night ice cream run. (No, really.)

Dryden only became GM after leading a lengthy search to fill the position that came up empty. After missing out on several candidates (with rumours saying he wanted Bob Gainey), Dryden took the job himself and held it for two years.

The Dryden era was marked by plenty of political maneuvering in the Leafs’ front office, a situation that continued for years after he relinquished the title. But it also featured the reemergence of the Leafs as contenders, thanks largely to landing Joseph in what still stands as the team’s best-ever free agent signing.

No. 8: Lou Lamoriello (2015–2018)

Record: 118-95-33

Signature move: Drafting Auston Matthews first overall in 2016.

It’s tough to rank Lamoriello’s work, as the young team he helped build is still very much a work in progress. Some of the key pieces were already in place when he arrived, and landing Matthews involved a healthy dose of lottery luck. Still, Lamoriello made some key moves, including dumping the Dion Phaneuf contract and adding Frederik Andersen. We’ll slot him in the middle of the pack for now, with the understanding that his tenure could look different within a few years.

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No. 7: Brian Burke (2008–2013)

Record: 129-135-42

Signature move: Trading for Phil Kessel in 2009.

Is this too high? It seems kind of high. Burke arrived in Toronto with all sorts of hype and bluster, then missed the playoffs every year. Given what he was brought in to do, there’s really no question that he failed in Toronto.

So how does he rank in the top half of our list? Well, as we’ve seen so far, he’s not exactly up against a Murderer’s Row of competition. But more importantly, Burke excelled at one of the most important aspects of the GM’s job: making trades. When it comes to pulling off deals, there’s really only one other name on this list that can rival Burke’s track record. In an era where other GMs were constantly mumbling about how hard it was to put a trade together, Burke was able to consistently fleece teams in deals for players like Jake Gardiner, James van Riemsdyk and Dion Phaneuf. Even the Kessel deal, often held up as Burke’s greatest blunder, landed the team its leading scorer for the next half-decade or so. If that’s your worst trade, you’ve had a pretty good run.

Most of those robberies didn’t pay off, because Burke’s hiring, drafting and contract negotiating never kept up with his wheeling and dealing. So yeah, he might be too high on this list. But we’ll give him a few bonus points for being among the last of his kind — a GM with the guts to actually swing for the fences when it came time to make a deal.

No. 6: Charles Querrie (1917–1927)

Record: 127-133-10, two Stanley Cups

Signature move: Signing early stars like Hap Day, Ace Bailey and Babe Dye.

Querrie’s name isn’t well-known among Toronto fans, and he technically wasn’t ever in charge of the Maple Leafs — his time at the helm preceded the team adopting that name.

Instead, Querrie headed the Arenas and St. Pats through the league’s tumultuous first decade, stabilizing the franchise and setting the stage for everything to come. Winning two Cups and seeding the team with a solid core of players for the future were nice, but Querrie’s most important accomplishment came as the team’s majority owner: simply keeping the team alive as the fledgling NHL struggled to find its feet.

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No. 5: Pat Quinn (1999–2003)

Record: 169-109-35-15

Signature move: Trading for Owen Nolan at the 2003 deadline.

Quinn held the dual role of coach and GM for four years, meaning the Leafs were very clearly his team. He used that power to build a team that was old, expensive and thoroughly unlikable.

They also won. A lot. Quinn’s teams were in the running for the Stanley Cup every year, and he holds the highest winning percentage of any Maple Leafs GM. And he wasn’t afraid to swing for the fences, adding players like Alexander Mogilny, Ed Belfour and Joe Nieuwendyk, while nearly landing Eric Lindros in 2001. The deal for Nolan was a classic Quinn move — it cost a fortune, and didn’t ultimately result in a Cup win. But it made a good team even better, which is all Quinn ever seemed to do in Toronto.

No. 4: Jim Gregory (1969–1979)

Record: 334-324-130

Signature move: Signing Borje Salming out of Sweden in 1973.

Gregory was the first GM to have to do most of his work under Ballard, so he was starting with two strikes against him. But he still managed to have a decent amount of success, including eight playoff appearances, and found three future Hall of Famers in Darryl Sittler, Lanny McDonald and Salming. (The latter of which Gregory could scout and sign only because Ballard was in jail at the time.)

No. 3: Cliff Fletcher (1991–1997)

Record: 202-200-58

Signature move: The 10-player Doug Gilmour trade, still the largest ever pulled off in NHL history.

Fletcher’s overall record isn’t that impressive; he actually lost more games than he won if we count his return to the job for an interim stint in 2008. But it’s hard to overstate the importance of his arrival in Toronto in 1991, and what he was able to do in the ensuing years. Fletcher took over a team that had spent a generation as an utter joke. Within a year, he’d transformed them into a contender, building what still stands as the most beloved Leafs team of the modern era.

He did it with aggressive trades, not just for Gilmour but for future Hall of Famers like Grant Fuhr, Dave Andreychuk and Mats Sundin, as well as by plucking Pat Burns out of Montreal. His reliance on veteran talent eventually caught up to him in Toronto, and his “draft schmaft” philosophy ultimately set the team back. But while he never delivered the Cup that seemed so close in those Gilmour-era days, he brought Leafs fans something that had seemed even more elusive: hope.

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No. 2: Punch Imlach (1958—1969, 1979—1981)

Record: 433-359-159, four Stanley Cups

Signature move: Signing and developing Dave Keon in 1960.

Imlach remains the last GM to build a Stanley Cup winner in Toronto, having put together the legendary “Over-the-Hill Gang” that took home the 1967 title. It was the team’s fourth under Imlach’s guidance (as both coach and GM), and spelled the end of the last truly great era of Maple Leafs hockey.

His return to the job in 1979 didn’t result in quite the same level of success; those two seasons are best remembered for Imlach dismantling much of what Gregory had built, including dealing away Sittler and Lanny MacDonald. There’s no doubt that tarnishes his legacy in the eyes of Leaf fans. But not enough to erase the glory years of the 1960s.

No. 1: Conn Smythe (1927–1955)

Record: 706-550-248, seven Stanley Cups

Signature move: Acquiring King Clancy from Ottawa, using money won in a horse race.

Apologies if you were hoping for more suspense at the top of the list, but there’s really no way to make the case for anyone other than Smythe in the top spot. Smythe spent nearly three decades as not just the Leafs’ GM, but as its owner and the architect of everything the franchise would become. He gave the team its name, adopted their famous blue-and-white color schemes, and built Maple Leaf Gardens.

Oh, and he won championships. Smythe guided the Leafs to seven titles, including six in the decade between 1941 and 1951. He yielded the GM’s duties to Day in 1955, and eventually sold his ownership stake to his son Stafford. He was elected to the Hockey Hall of Fame in 1958, then oversaw the construction of the actual HHOF building 1961.

It’s fair to say that Dubas will have a long way to go before he gets mentioned in the same breath as Smythe, let alone matches his achievements. But if you’re a Maple Leafs fan looking for a good omen, consider this: Smythe’s three-decade journey as the greatest GM in team history began when he took the job in 1927, when he was just 32 years old.