Which team makes the best roster of stars who won a Cup somewhere else?

We’re down to four teams left in the playoffs, and that list feels like it’s about to get even shorter. Pretty soon we’ll have our final two, and the odds say that your team is probably long gone. Maybe they were never around to start with.

But maybe a few of their former players are. That’s always a bittersweet storyline for a hockey fan. Assuming the player left on good terms, you still have some loyalty and might want to see them do well. But watching a player win a Cup somewhere else when they couldn’t do it for your favorite team isn’t exactly ideal. You’re happy for them. You just can’t help but think of what might have been.

Today, let’s celebrate those guys with a simple question: Which team can build the best six-man roster out of guys who won the Stanley Cup somewhere else?

I like this topic because it feel like one of those questions that just about every fan base probably thinks they’ll do well in, because we all think this happens to our team more than most. We’ll see about that. But first, a few ground rules:

• We’re looking for three forwards, two defensemen and a goalie, without worrying about position beyond that.
• We’re looking for players who had an impact with a team, then left and won their first Stanley Cup somewhere else. If they won a Cup with your team first and then won another somewhere else, that obviously doesn’t count. Neither do guys who already had a ring before they arrived on your team.
• You get credit for whatever the player did with your team. So the longer they stuck around, and the higher their peak when they were there, the better. A big-name superstar won’t help you much if they only had a brief cameo with your team.
• Finally, we’re only looking at Cups won as a player – going somewhere else and winning as a scout or a coach or whatever doesn’t count.

As always, I’ll aim to do ten teams or so and then turn it over to you in the comments to add any additional contenders.

It should go without saying that some teams will make for better options here than others. Teams that have been around longer have more runway to work with, and teams that go long stretches without Cups will also have a big advantage. Wait, did I just accidentally design a roster-building game where the Maple Leafs are the team to beat? I might have, so let’s start with them…

Toronto Maple Leafs

They haven’t won any Cups since 1967. Did you know that? It doesn’t get brought up all that often.

Forwards: Lanny McDonald, Phil Kessel, Vincent Damphousse

Defensemen: Tomas Kaberle, Carl Gunnarsson

Goalie: Bernie Parent

The Maple Leafs start us off with a strong team, although maybe not quite as strong as you would have thought. Their Original Six era stars all won Cups in Toronto, and many of the biggest names since never won at all, which takes out guys like Mats Sundin, Darryl Sittler, Borje Salming and Wendel Clark.

Still, we’ve got some strong talent to work with, starting with Hall-of-Famer McDonald, who had to wait until his final year in Calgary to write an OGWAC redemption story. Kessel went straight from Toronto to back-to-back Cups, and Tomas Kaberle only took a few months to get a ring after the Leafs sent him to Boston. I gave the third forward spot to the criminally underrated Damphousse, although we could have also gone with Tyler Bozak, Gary Leeman or Eddie Olczyk, and Nazem Kadri might lay claim to the job in a few weeks.

The weakness here is the second blueline spot, and our goalie isn’t as impressive as it seem since we’re only getting two seasons of Parent before he headed back to Philadelphia to become a superstar. All in all, the Leafs aren’t bad, but they’re certainly beatable. As always.

Let’s try another Original Six team…

Chicago Blackhawks

We don’t have any recent names because they foolishly won multiple Cups in the last decade, but a 49-year drought should give us something to work with.

Forwards: Denis Savard, Steve Larmer, Phil Esposito

Defensemen: Allan Stanley, Cy Wentworth

Goalie: Eddie Belfour

We get off to a good start up front with two stars from the 1980s, with Savard getting his Cup in Montreal in 1993 and Larmer following the next year in New York. We’re only getting Esposito’s first four seasons, though, so it’s just the 60-point kid and not the 70-goal monster.

The blueline isn’t good; remember, Chris Chelios had a Cup from Montreal before he arrived, so him getting another in Detroit after he leaves doesn’t help us. Doug Wilson never won a Cup, and neither did long-time Hawks like Bob Murray or Keith Magnuson, so we’re scrambling to fill the defense slots (and not getting anything close to Stanley’s best years). But we’ve very strong in net thanks to Belfour’s Cup in Dallas, so it balances out into a very solid entry.

We’ll come back to the Original Six, but let’s try some of the expansion era teams.

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