Worst General Managers in NHL History

by Micheal Aldred on April 23, 2009 in Uncategorized - 156 Comments

Part 3: 20 Years of Maple Misery
From Gord Stellick to Cliff Fletcher Version 2.0

It’s been over 40 years since the Leafs won the cup and while others make fun of the fans for continuing to cheer, here is an overview of why you shouldn’t make fun, but feel bad for them…


Let’s Begin with Gord Stellick – April of 1988 to August of 1989 – who quit because there was too much interference by Harold Ballard.

His Infamous Trade: On November 7th, 1988, he dealt Russ Courtnall to the Montreal Canadiens for John Kordic and a 6th round pick in 1989 (Michael Doers).

People still complain about how lopsided that deal was, and in a recent interview with the Toronto Star, he’s still a bit ashamed of it.

“When Punch Imlach traded Lanny McDonald to Colorado he went right out of sight,” Stellick said. “Unfortunately for me, it seemed Russ was on TV every Saturday in Montreal, with his perfect teeth and scoring four goals a night, even though he only had 22 for them that year. He was a sexy player.”

He’s right, you know, Courtnall was pretty sexy, but that is besides the point. What must be discussed is this “perfect teeth” syndrome – a disease only terrible hockey players suffer from.

Seen Here: Pure Sex Appeal. Just look at those teeth!

Courtnall went on to score 82 goals and 195 points in 240 games. John Kordic, on the other hand, posted just 16 points, but an impressive 437 PIMs for the Leafs in 101 games. Unfortunately, he’s best remembered for being the guy who overdosed on cocaine and steroids and was beat by 6 police officers until he died just moments later in an ambulance, still bound by rope and cuffs.

Floyd Smith: 1989 to 1991 – the man who acquired Mike Foligno.

Infamous Trade: On October 16th, 1991, Floyd Smith dealt Toronto’s 1st round pick in 1991 to New Jersey for Tom Kurvers. Kurvers, a young offensive defenseman at the time, played just 89 games for the Leafs, collecting 55 points in the process, before he was dealt in January of 1991 to Vancouver for Brian Bradley, a small centerman who scored just 10 goals in the 85 games he played in the blue and white. Toronto’s 1st round pick became the 3rd overall pick after an abysmal season by the Buds, and the Devils used that pick to select none other than Scott Niedermayer.

Cliff Fletcher: 1991 to 1997 – the guy who brought us Doug Gilmour and Pat Burns.

Infamous Trade: Everyone knows he made that big crazy deal that landed Doug Gilmour and company, but what people forget is the trade he made with the Islanders. You see, Cliff is not only known as the “Silver Fox”, but also “Trader Cliff” as he followed the theory of “draft schmaft”. He dealt Toronto’s 1st round pick in 1996 which ended up being Dainus Zubrus, to the Flyers for Dmitri Yuskevich. But that isn’t the trade I’m talking about, is it Cliff?

“I don’t know what you’re talking about.”

Of course you don’t. But the secret is about to be revealed, Cliff. Toronto wanted Wendel Clark back, and they had to swing a deal with the Islanders to get it done. But that’s alright, because then general manager Mike Milbury, who we’ve already discussed, was terrible at trades. Well not this time.

On March 13th (Unlucky? Yeah, I definitely think so), the Leafs dealt Kenny Jonsson, Darby Hendrickson, Sean Haggerty and a 1st round pick in 1997 to the Islanders for Wendel Clark, Mathieu Schneider and D.J. Smith.

No, not that D.J. Smith.

At first thought, the trade is a tad one-sided. On second thought, knowing the first round pick became Roberto Luongo, it is HORENDOUSLY one-sided. Somehow, I think the whole “draft schmaft” thought should be written on a big brick and provided to Cliff where he publicly shoves it somewhere inappropriate.

Ken Dryden: 1997 to 1999 – the guy who brought us Pat Quinn.

Infamous Move: Bringing us Pat Quinn.
You see folks, life would have been a lot different had Pat Quinn not been brought on board. Not only would he have not become the Leafs general managers (which occurred in 1998) but we would not have suffered the whole “young players can be dealt for the retirement home” theory Quinn lived by.

Seen Here: Pat Quinn answers questions after camping out over night for his own press conference.

Yes, the reason why hiring Pat Quinn as coach and later offering him the general manager position was so terrible is that Ken Dryden had another man in place for the role. Bob Gainey. The two were interested in reuniting since their playing career in the management field, but once Quinn heard Gainey was the “second” choice (yes, I’m thinking the same thing you are) he immediately took the reins and ran the team into the ground. You’ll learn about that soon enough.

Or how about Now?

Pat Quinn: 1999 to 2003 – the guy who brought us frustration.

Infamous Trade: The Boston Bruins were angry with an arbitration ruling on Dmitri Khristich’s contract and thus Pat Quinn was there. The Bruins refused to sign him (thus making him a free agent) but before that could be made official, Pat Quinn dealt a 2nd round pick for him. Khristich, at the time, had just posted back to back 29 goal seasons. It wasn’t necessarily the trade itself that was horrid, but the aftermath. Not only did Khristich only tally 15 goals in 80 games for the Leafs, but they had to make room for him on the roster, so Toronto took a young guy by the name of Steve Sullivan and stuck him on waivers. He was claimed by the Blackhawks and the rest is history.

“But I still got one of these!” – Yes, but you still suck.

Because on March 5th, 2003, Pat Quinn dealt Alyn McCauley, Brad Boyes and a 1st round pick (Mark Stuart) to the San Jose Sharks for Owen Nolan. Nolan became an often injured player, despite notching 60 points in 79 games for the Leafs. He was then bought out and became nothing but a thing of the past and cap space of the future. Boyes, on the other hand, has gone on to become a 30+ goal scorer who would look horrible in a Leafs jersey right about now.

John Ferguson Jr.: 2003 to 2008 – the guy who brought us Andrew Raycroft.

Infamous Trade: It goes without saying, everything this guy did was destined to fail. Raycroft sucked, Leetch was acquired for a 1st, 2nd and prospects to play a whopping 15 games (in which he had a point a game), Blake signed a 5 year deal then suddenly found out he had cancer, and then he traded a 1st, 2nd and 4th for Vesa Toskala and Mark Bell. The 1st rounder ended up having an opportunity to draft Angelo Esposito, who’s draft value dropped significantly. It’s difficult to pinpoint just one trade in which people will look back on and say “yeah, that was bad” because every single decision he made seemed to be for the worse. He was simply a God at fuck-ups.

Seen Here: Ferguson, just seconds before completing another shitty deal.

Cliff Fletcher (The Return): 2008 to later 2008 – the guy who got rid of McCabe, Tucker and Raycroft.

Infamous Deal: Other than a reunion of the whole “draft schmaft” concept as the Leafs trade a 3rd, 5th, and 4th away in deals involving a return of Mike Van Ryn, Ryan Hollweg and Jamal Mayers, I will give Fletcher credit in moving up to steal Luke Schenn 5th overall at the entry draft. However, he would follow that up with a trade that will go down as the definition of “idiocy” in the hockey history books.

On November 24th, 2008, just 5 days before he would be replaced by Brian Burke, Fletcher completed what was hopefully the last terrible trade made by the Leafs before moving into a new era in which the “suck” factor is turned down a notch or four. He sent Alex Steen and Carlo Colaiacovo to the St. Louis Blues for Lee Stempniak. Lee tallied 13 points in 14 games for the Blues on the year and finished off the season with 31 points in 61 games as a Leaf. Steen and Colaiacovo combined for 53 points for the Blues. The trade lifted the Blues into playoff contention this season, while the Leafs finished in the bottom half of the league, as per usual. What made the trade even worse is Cliff Fletcher being quoted as saying “I wasn’t sure the trade would get done because of how good Stempniak was playing”. What? Is that to say you were going to give up more? I tend to wonder if he was watching the wrong player.

Seen Here: David Perron

A Possible Scenario:

Cliff: This kid is amazing! We should trade for him.
John Davidson (Blues GM): Who?
Cliff: Uh, his jersey is 50 something, uh 57?
John Davidson: What would you offer?
Cliff: Carlo Colaiacovo and Alex Steen.
John Davidson: Oh, you’re talking about Lee Stempniak.
Cliff: Not sure, his number is 50 something.
John Davidson: No, you’re thinking 12.
Cliff: Could’ve sworn it had a 5 in it.
John Davidson: No, you see Cliff, a 2 looks like an upside down 5, so your mind is confusing you.
Cliff: Oh, yeah, you’re right. So those 2 for Stempniak?
John Davidson: Sure, just sign here.

To read more “Worst General Managers in NHL History”, click Here for Part 1 and Here for Part 2 or visit Checking From Behind for more.

Micheal A. Aldred
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