NHL teams that lost out in the Cup Final only to win it soon after

So at the time of writing this it is July 1, which is significant in a few key ways. Not only is it Canada Day, and the start of NHL free agency, but it's also the one week anniversary of the Edmonton Oilers losing in game seven to Florida in the Stanley Cup Final.

Now many of you might be asking - why would I bring this up now? Am I a masochist? No. Believe it or not, this is actually a step forward. NHL history has shown that you must lose in the Cup Final before you can win. It's something you can take the bank. When I made my prediction here, there was literally no doubt in my mind that the Oilers would come out victorious - and if we're being honest, in my defense, they very nearly did, only missing by a mere two goals. But perhaps I was blinded by elation and emotion, not hallmarks of who I am as a sports fan. I thought the McDrai duo, a combination lethal to the opposition, would overcome NHL tradition. But I was wrong.

If Wayne Gretzky and Mark Messier could lose in 1983, then surely Connor McDavid and Leon Draisaitl could lose in 2023. In hindsight I realize that now. I did tip my hat to Florida as opposition when I made my prediction, though, going into the series with my mind wide open knowing full well they were also a good team and could also win it. There was also the very real history of both the regular season and playoffs when the Oilers came back from adversity time and time and time again, so I had that going for me too, as did all Oiler fans.

Last Monday night, a friend of mine was watching the game at his house while I was watching it at mine. (I have a part time job whose schedule is in the late afternoon-early evening, so I was only able to give a portion of the game my full attention). He wanted to go out and see how Whyte Ave. was doing at a time like this, so he drove to my place and we went there and, as expected, was very quiet. There's an ice cream place my friend likes to go on Whyte, and since I'm down on my luck job wise right now he treated me. While we were in line, a guy walked past me saying "blow it up" - not literally, of course, but referring to the team. This is, of course, a sentiment not based on reality or logic - as the smart sports fan judges their team on - but strictly on emotion.

Did it suck to lose last week? Yes it did, even for a less emotional fan like myself. But, is it the end of the world or the start of another rebuild? Absolutely not. The NHL is filled with teams who lost in the Cup Final one year, only to win not soon after. Let's go through some of those teams now:

New York Rangers, 1937 - The New York Rangers lost the Cup final in 1937 to Detroit, only to rebound in 1940 against the Toronto Maple Leafs to win.

Toronto Maple Leafs, 1936, 1940 - The Leafs lost to Detroit in 1936 and to those same Rangers in 1940, before winning it all - against Detroit, no less - in 1942.

Toronto Maple Leafs, 1960 - The Leafs lost in 1960 against Montreal, only to go on to win in 1967 against Montreal. How mad do you think the people of Montreal were that year?

But this was the original six era, you say, where you practically had to bunch your huggies not to make the playoffs? Well, prepare to be amazed.

Calgary Flames, 1986 - The Flames would lose in 1986 - Patrick Roy's first full season in the NHL, no less - to Montreal, only to beat the Habs three seasons later in 1989. This 1989 date in history is also significant as it would later spawn a great joke - "What's the difference between the Calgary Flames and a bra?" "A bra has two cups." Lol, hope you enjoyed that one.

Montreal Canadiens, 1989 - They would lose to the Flames in 1989, only to come back to the Final in 1993 and beat Gretzky and the LA Kings - subsequently the last appearance in the Cup Final of his career.

Detroit Red Wings, 1995 - Ah the neutral zone trap era - this Final likely goes down as one of (if not the) most boring Cup winners to watch in NHL history. Anyway, the Red Wings lost to New Jersey in '95 before winning two straight in 1997 and 1998, starting Ken Holland's legacy as a GM with the golden touch.

New Jersey Devils (reverse order), 2000 - This is a weird one. The Devils won the Cup in 2000, only to get back to the Final but lose in Colorado the next year. How do you think that loss would've felt for Devils fans? Experiencing the thrill of victory before the bitterness of defeat? No other team has really done it in this order since, except for Tampa Bay. But never fear, for the Devils avenged that loss in 2003 when they won against the Ducks. Speaking of which....

Anaheim Ducks, 2003 - The Ducks lost to New Jersey in 2003 before coming back to the Final in 2007 and winning it all against the Ottawa Senators, for the franchise's one and only Stanley Cup win so far. They're still rebuilding at this time, so don't count on them going back to the Final anytime soon.

Pittsburgh Penguins, 2008 - The Pens lost to Detroit in 2008, only to come back from the experience and flip the script, beating Detroit in 2009 then San Jose and Nashville in 2016 and 2017 respectively.

Tampa Bay Lightning, 2015 - The Lightning lost to Chicago in 2015 only to come back and win two straight during the covid era of 2020 and 2021, then would go on to lose against Colorado in 2022 - the other reverse order.

Vegas Golden Knights, 2018 - The Vegas Golden Knights lost in 2018 to Washington only to make it back to the Cup Final in 2023 and beat Florida, which then brings us here.....

Florida Panthers, 2023 - The Panthers lost in 2023 to the Golden Knights, only to beat the Oilers in 2024 to win it.

That's many examples of teams that had to lose before they would win - and that's why they play the games, as the cliche goes. Some teams, like the Blackhawks of the 2010s, were just so loaded at every position they didn't have to lose a Cup Final before winning one. Ditto the LA Kings of the 2010s as well.

Others, like the 1991 and 1992 Pittsburgh Penguins, won their first cup in franchise history in 1991 largely because their opponent was a cinderella story that wasn't supposed to be there in the first place in the Minnesota North Stars. But history shows those teams are the exception, not the rule. It could be much worse - other teams like Ottawa, Nashville, San Jose, Buffalo, and Vancouver have appeared in Cup Finals but have yet to win one.

The million dollar question, though, is this - Will the Oilers repeat Florida's history and win the Cup in 2025 after losing it in 2024? Maybe. As an Oilers fan, I hope so. It may not be next season, but I believe the Oilers are more primed than ever to win a Cup going forward. Gretzky once told McDavid in this interview that he was too good NOT to win the Stanley Cup, and I believe him.

The Oilers WILL win the Stanley Cup, it's just a matter of when, not if. You can quote me on that.

Meanwhile, around the NHL

A few major trades went down over the last week or so.

First off, the long rumored move of Jakob Markstrom to New Jersey was completed. This was apparently supposed to have materialized at the deadline, but it collapsed at the last minute. It's been completed now. I will never in my life understand why teams like this guy so much - he's never been actually good outside of maybe two seasons. He's proven himself to be an average, underperforming goaltender. Either way, he's New Jersey's problem now. In exchange the Flames got a fairly decent guy who just became an NHL regular last season with the Devils in Kevin Bahl. The Flames have been forced to completely retool their roster on the fly, as veterans get tired of playing for a team that's obviously going nowhere at this point and with an ownership group that seems oblivious to reality and won't let them go full fledged rebuild. By the way the Flames are now almost $6 million dollars below the cap floor, so they're going to have to make moves of some kind, otherwise they risk repercussions from the league. But hey, good luck convincing anyone to sign with your dumpster fire of a franchise....

Then there was a big problem child trade that went on - Pierre-Luc Dubios went to Washington in exchange for Darcy Kuemper straight up. The feeling here is Dubois will ride shotgun with Alexander Ovechkin and help him try and break Gretzky's all time goal scoring record before he runs out of gas. Guess the caps miss Nicholas Backstrom more than they thought....meanwhile Kuemper is an oft-injured goaltender. The guy's been in the league for 13 seasons but has only played 50+ games in three of them and has only played in 30+ games in five of them. Not a great track record for goalie durability. On paper this is trade that should work out well for both teams.....but there's huge risk on both sides. If Dubois's fresh start doesn't pan out, the Caps will have an $8.5 million boat anchor on their roster for another seven seasons, not a promising prospect. Not to mention they've only got one more season of Backstrom's LTIR cap space, so they'll have to figure out how to pay for Dubois regardless after this coming season. Meanwhile, Kuemper, when healthy, is a very good goaltender, but so far he's basically been the goaltending version of Marion Gaborik - when healthy, very good, but often not healthy. This is technically a re-acquisition for them, as Kuemper played for the Kings in 2017-18.

Then there was Ottawa trading Joonas Korpisalo to Boston in exchange for Linus Ullmark. The nets are now Jeremy Swayman's to lose in Boston, while Korpisalo, with a reduced role and less pressure, at least in theory should rebound. Goaltending held the Sens back last season from what they could be, and on paper at least Ullmark should provide the Sens with what they need. I certainly wouldn't count out the Sens from a playoff spot next year with Ullmark in net.

The Flames also dumped malcontent Andrew Mangiapane to Washington for Colorado's second round pick next season. This makes a ton of talent that has exited the Flames at all three positions - Matthew Tkachuk, Johnny Gaudreau, Mangiapane, Chris Tanev, Noah Hanifin, Jakob Markstrom, Nikita Zadorov, Elias Lindhom - that's a huge chunk of their core from the last season or two. The Flames will look very different next season, and frankly I don't know who in their right mind will sign with them so they can reach the cap floor. Maybe a native Calgarian warm body can sign with them, a hometown boy is the only person I can really think of that might even consider it. GM Craig Conroy certainly has his work cut out for him, and I wouldn't want his job right now.

The Pittsburgh Penguins then picked up Kevin Hayes from the Blues for "future considerations" - aka nothing. I know Hayes has been underperforming the last two seasons, but....nothing? Seriously? Not a mid-low end draft pick? Hayes has 713 games of NHL experience and thus will be a great veteran presence in Pittsburgh. Nothing? Man did the Blues ever gets fleeced on this one.

The Washington Capitals traded for Logan Thompson from Vegas in exchange for two draft picks. So now we know who's going to replace Kuemper in Washington. I wonder who's going to tandem with Hill in Vegas now......is Robin Lehner healthy enough to play out his contract now? I wonder......

The Utah hockey club made two separate deals with Tampa Bay and New Jersey, to bring Mikhail Sergachev and John Marino into their defense corps for next season and beyond. Definitely two good trades that will make that team better. I wouldn't go so far as to say they'll be in the playoffs next season, they were a pretty bad team last year, but they're definitely better than last season. Funny how players actually want to sign with you when a move to another city isn't looming.....fun fact - the Oilers second round pick in 2025 that they traded away to Arizona in the Zack Kassian trade went to New Jersey as part of the Marino trade. The only roster player of any relevance they really gave up was Conor Geekie. Pretty good deal for them, for sure.

And last but not least, the Oilers made a trade with Philly for the 32nd pick in the first round for their first rounder in either 2025 or 2026 for Florida's first rounder this year at the draft table, so they could draft Sam O'Reilly, a player who already cracked the 20 goal and 50 point marks in his first full season of junior hockey for the London Knights of the OHL. He looks like a keeper, we'll see how his development goes.

Other Oilers news

Calvin Pickard and Cam Dineen re-upped - Pickard was re-upped for $2 million over two seasons ($1 million AAV), while prospect blueliner Dineen was signed to a two way contract at $775,000 per at the NHL level ($1.55 million total). Dineen is not one of the surefire NHL prospects at this time, we'll see what he does over the length of the contract.

Jack Campbell bought out - I was honestly hoping the Oilers could trade Campbell somewhere before exploring this - maybe Vegas where Campbell has the same cap hit as Lehner, or Washington prior to them trading for Thompson, or Seattle or Detroit where their goaltending is nothing to write home about. But, for all I know, maybe Holland already explored this option and found it wanting. The move will save the Oilers $3.9 million this upcoming season, $2.7 million two seasons from now, and $2.4 million three seasons from now before costing $1.5 million for the next three seasons after that. It remains to be seen what the Oilers will do with that cap savings.

Ken Holland and Oilers mutually part ways - His contract was up as of June 30, and it won't be renewed. It always seemed a bit odd to me that the Oilers didn't want to renew the contract of the GM who had built their team into a Stanley Cup contender - and on the surface that's certainly what it looks like. However, it was evident that as soon as Bob Nicholson moved into an advisor role from running the hockey ops, and the Oilers hired Jeff Jackson to replace him, we all knew there was some possibility that Holland's days were numbered regardless of how he does at the helm. Holland, after all, was a Nicholson hire, and so when your boss moves out or to a different role than before, you don't have that protection in your job on an NHL team. Holland was also believed to acknowledge that Jackson would likely want to "hire his own guy" so to speak. The Oilers, while largely satisfied with Holland's performance, were thinking they might want to get younger at the position. After all, Holland is 68, and he has children and grandchildren, and with $25 million made from just working with the Oilers alone, not to mention whatever he made all those years in Detroit, he has the cash to determine his own destiny. We don't know at this point whether he will simply retire or take a job with another NHL club. Jackson himself will be the interim GM, and now he has a chance to really put his own stamp on this club. Internal candidates for the GM job are believed to be Keith Gretzky, current assistant GM (and primary GM For the Condors) and interim GM for the club after Peter Chiarelli was fired, current capologist Bill Scott, and assistant GM Brad Holland, who oversees pro scouting for the Oilers right now.

Oilers cup run makes a $200 million economic impact to the City of Edmonton - At this point it's pretty safe to say that Daryl Katz's investment in the Oilers in 2008 has paid off in spades for him. The Oilers are now a top 10 NHL team in terms of their books and profit margins, and this past playoff run has only enhanced that. Part of that boon for the city must've been in increased revenues from the Community Revilatalization Levy put down for many years to come as part of the funding formula for businesses surrounding Rogers Place, who surely saw a surge in business on game days themselves. So no need to feel sorry for them that they have to pay extra taxes. Congratulations to Katz, he has built the Oilers into a business entity that consistently punches above it's weight class.

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