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The storied, sometimes questionable and funny, history of one of sports’ greatest trophies

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(CNN) — It’s one of the most recognizable trophies in sports, with a history dating back to the 19th century, so it’s no surprise that the Stanley Cup has a story or two to tell.

Named after Lord Stanley of Preston, a Canadian governor general who donated the first Cup back in 1892, the trophy is awarded to the NHL champions every year.

It is, and always has been, the pinnacle of the sport and something players dedicate their entire lives to winning.

With that being the case, it’s perhaps predictable that those who manage to get their hands on the trophy are keen to celebrate, especially since it is tradition that every player of the winning squad gets to spend an entire day with the prized silverware.

Problem is, that’s left the poor old Stanley Cup in some unusual situations. CNN Sports looks at some of the most bizarre predicaments it’s ended up in.

1924

Montreal Canadiens

In almost cartoon-like fashion, the Montreal Canadiens left the trophy on the side of the road after winning it in 1924. The story goes that a car carrying some of the team had stalled going up a hill, meaning players had to get out to push. It wasn’t until they reached the top that they realized they had left one of the most famous trophies in the world behind!

Prized possession

The Stanley Cup is looked after by a team of people with the title of “Keeper of the Cup.” These people travel with the trophy, keeping it clean and, more importantly, safe. At least one member of the team is always with the trophy when it’s in public. “We get called different things too. People have fun with it. They call us Cup keepers, Cup dudes, Cup guys. You know, handlers is all kinds of terms, but in essence, we’re basically babysitting the Cup,” Howie Burrow, Keeper of the Cup, told CNN Sports.

1987

Edmonton Oilers

It’s only natural that players want to party after finally getting their hands on the trophy and that seemed to be the case with the Edmonton Oilers following the magical final series in 1987, where the Oilers blew a 3-1 series lead, but managed to pull off the win in Game 7 against the Philadelphia Flyers. Led by Mark Messier, both on and off the ice, the Oilers reportedly went partying to celebrate and accidentally damaged the Stanley Cup over the course of the night, requiring repairs before being returned.

Global tour

The Stanley Cup has traveled to dozens of countries around the world, including places such as Afghanistan, Japan, Scotland and the UAE. It doesn’t get a first-class seat, though. Instead, it flies underneath the airplane in a very secure box. “When I’m getting my boarding passes, I’ll open it up to show whoever’s checking me in, but soon as I do that, there’s usually about a dozen people in the other lines going, ‘Oh my God, that’s a Stanley Cup. Can I get a photo? Can I touch it?’” Burrow told CNN.

1991

Pittsburgh Penguins

One thing the trophy’s handlers insist on is that the Cup shouldn’t get wet – although that didn’t stop the Pittsburgh Penguins. Now legendary photos show the team celebrating with the trophy in Canadian star Mario Lemieux’s swimming pool. Luckily, though, it seems like the trophy floated.

All shapes and sizes

The Stanley Cup we see today has been the same shape since 1948, but it hasn’t always looked the same. The first ever iteration of the trophy, back in 1892, was just a bowl and was called the Dominion Hockey Challenge Cup. Over the years, more tiers have been added to it and now the Cup stands at 35.25 inches and weighs 34.5 pounds. “If you have to hang on to it for a long time and say, you have to walk a block or two because you’re following somebody, it does get heavy. You’re switching arms, or you got to put it down. You can work up a good sweat. But when the players first win it, right after on the ice, I mean, I’m sure it weighs hardly anything to them,” Burrow said to CNN.

1994

New York Rangers

It seems even animals can enjoy the “People’s trophy.” In 1994, a photo was taken of Kentucky Derby winner Go For Gin eating out of the trophy while at New York’s Belmont Park. New York Rangers star Eddie Olczyk was rumored to be behind the stunt, but he’s since denied responsibility.

Etched into history

Each player of the winning team has their name etched into a band which is then placed onto the trophy – with older bands being retired through the years. Given the number of winners, it’s not surprising that a few spelling mistakes have creeped onto the prestigious Cup.

2008

Detroit Red Wings

What’s the worst thing you could imagine happening to – or in – the Stanley Cup? Well, this might be it. When Kris Draper had his day with the trophy, he celebrated by putting his baby daughter in the Cup for a photo. Only she left behind a little surprise… by using the legendary trophy as a toilet.

Summer tour

Since 1995, every player who wins the Stanley Cup is allowed a day to celebrate with it – sometimes two – in any way they deem fit. The trophy is then returned to NHL trustees before the new season, meaning every team bids to win the prestigious trophy again.

2017

Pittsburgh Penguins

Forward Josh Archibald got creative and used his time with the Cup to baptize his son. Three-week-old Brecken was photographed receiving his blessing while sitting in the bowl at the top of the trophy. Quite the experience for someone not even a month out in the world.

Record winners

No team in history has gotten its hands on the Stanley Cup more than the Montreal Canadiens. The Habs have won it 24 times, including a record five-in-a-row from 1956 to 1960. The franchise’s first win came in 1916 – before the NHL even ran the tournament. The Canadiens haven’t won it since 1993, though, and last reached the final in 2021.

2018

Washington Capitals

In 2018, Capitals defenseman Dmitry Orlov decided to celebrate with the trophy in his hometown, the southwestern Siberian city of Novokuznetsk. The Cup had to take a myriad of connecting flights to reach the destination and you can probably guess what happened. The trophy missed one of its flights and was left behind in Moscow. A helicopter was chartered in order to reclaim it quickly!



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Evian Championship: Grace Kim produces improbable late comeback to clinch first major

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CNN
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Grace Kim produced one of the most remarkable comebacks you are ever likely see as she clinched the Evian Championship to become just the fifth Australian woman to win a golf major.

The 24-year-old was three shots off the lead with four holes left to play in Sunday’s final round, but closed with birdie, birdie, par and eagle to draw level with Thailand’s Jeeno Thitikul at the top of the leaderboard and force a playoff.

However, the comeback looked like it would end early as she hit her second shot on the first playoff hole into the pond by the 18th green.

But remarkably, Kim chipped in from where she had taken a drop to force the playoff to a second hole, where she sunk a 20-foot eagle putt to seal the most improbable of major triumphs.

“Obviously, it’s a huge achievement for me,” Kim said, per Reuters. “I’ve had a lot of doubts early this year. I was kind of losing motivation.

“I kind of had to get some hard conversations done with the team. Yeah, kind of had to wake up a little bit. So to be sitting here next to this trophy is definitely surreal.”

Kim, who battled a cold throughout the tournament, has struggled on the LPGA Tour since winning the Lotte Championship in Hawaii in 2023, her rookie season.

She had recorded just one top-10 finish in her last 11 appearances, per Reuters, and earlier this year slipped down to world No. 100.

But after securing her second LPGA Tour title, Kim has now joined exclusive company in Australian women’s golf.

Fellow Australian Minjee Lee, also a major winner, was watching from the side of the green as Kim sunk the winning putt, before running on to spray her with champagne.

Seven-time major winner Karrie Webb and three-time winners Jan Stephenson and Hannah Green also make up the exclusive club.

“I saw there is a picture of Karrie as you walk into the locker room, walking down 18 as well, so seeing that each day is motivating” Kim said.

“Obviously, Minjee’s first major was this one and this is now mine as well.”



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Amanda Anisimova vows to return stronger after being ‘frozen’ with nerves during Wimbledon final defeat

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London
CNN
 — 

It was billed as the Wimbledon women’s final that no one expected, it finished as a match that American rising star Amanda Anisimova will want to forget.

The 23-year-old always knew she was up against it, playing in her first grand slam final against a five-time major champion who has seemingly reinvented her game on grass.

But even the biggest Iga Świątek fan would never have predicted the 6-0, 6-0 thrashing that played out on Centre Court on Saturday.

The demolition job took less than an hour. It was also the first time since 1911 that a Wimbledon women’s final was won without the champion dropping a single game.

Everything went wrong for Anisimova, while everything went right for Świątek. The perfect storm, with two very different outcomes for either player.

“I think I was a bit frozen there with my nerves and maybe the last two weeks I got a bit tired,” a very poised Anisimova told reporters during her post-final press conference.

“It was a bit tough to digest, obviously, especially during and right after. It’s not how I would have wanted my first grand slam final to go.

“I think I was a little bit in shock after as well, but I told myself I’ll definitely come out stronger after this.”

Anisimova showed resilience by completing her on-court interview after the final.

Despite the heavy defeat in the final, we must not forget the incredible tournament that Anisimova has had at SW19 this year.

No one really tipped the world No. 12 for a title run on the grass, there were simply too many better players, with too much experience in this competition.

But as the big names dropped out of the women’s draw, Anisimova kept getting closer to her maiden grand slam final.

Then came a semifinal against world No. 1 Aryna Sabalenka. Ask Anisimova today and she might say she wished her tournament ended after that brilliant win.

The American showed everything that is great about her game against Sabalenka: Her booming backhand drawing gasps from the Centre Court crowd who started to fall in love with the youngster.

But, in truth, none of that form was on display during Saturday’s final. Her serve was left wanting and 28 unforced errors just demonstrated what state of mind she was in.

In her post-match comments, Anisimova said how she had struggled with the heat during the semifinal and thought that maybe could have caused her level to drop in the final.

She also said she felt fatigue during her warmup, but didn’t want to take anything away from her opponent’s “incredible” performance.

Straight after the match, Anisimova somehow mustered the courage to conduct her on-court interview, something that has become tradition at Wimbledon over the decades.

After brushing away the tears, she managed to speak so eloquently about what must have felt like one of the most difficult moments of her career.

But while she explained how she simply “ran out of gas” in the final, the love she showed her family and friends in the player’s box spoke volumes about the journey she’s been on.

In 2023, Anisimova stepped away from the sport, deciding not to touch her racket for months while she combatted what she described as burnout.

The time away from tennis was to help her own mental health, which had suffered after several seasons on the hamster wheel that is the professional tennis tour.

If bouncing from hotel to hotel is not enough, each tennis match is like a psychological game of chess. It’s no wonder that teenage prodigies, like Anisimova was, can quickly get tired of it all.

During the break, Anisimova said she learned a lot about herself, spending time with the people she loves and exploring new hobbies, one of which was art.

In 2024, she returned and set out proving people wrong.

After her semifinal win at Wimbledon, Anisimova told reporters that people had said she would never reach the top of tennis again after taking such a long break.

She previously said it was a “special” feeling to show how wrong doubters were at SW19 this year.

“My fighting spirit has gotten me to the final today,” she said as her tournament came to an end.

“It wasn’t me playing perfect. There were matches where I struggled and I wasn’t playing to my full potential, but I think just me staying focused and fighting my way through certain moments and focusing and also lifting myself up and trying to not get negative on myself was the most important thing.”

Anisimova says she felt fatigue in the buildup to Saturday's final.

No one needs to tell Anisimova that there will be brighter moments in her career to come.

If anything, this tournament has shown her game is good enough to reach a grand slam final while still having plenty of areas to improve – and that’s exactly what she’s promised to do going forward.

First, though, the more important things. Anisimova vowed to spend some much-needed time with her family and friends after they showed so much support throughout the tournament.

Whatever comes next in her career, though, you get the sense it will be driven from the feeling she felt on Centre Court during this year’s final.

“There’s a lot of improvement,” she said. “If anything, I think it’s more experience for me on how to handle nerves. It’s my first grand slam final, so at least I have that experience now.”



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Bill Ackman: Swift backlash after billionaire’s pro debut

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CNN
 — 

Billionaire Bill Ackman and organizers of a tennis tournament have been strongly criticized by former grand slam champions and social media after the hedge fund manager made his professional tennis debut, a match he ended up losing.

Ackman, who has a prominent social media presence on X, played with three-time grand slam doubles champion Jack Sock in the men’s doubles at the Hall of Fame Open – an event sanctioned by tennis’ world governing bodies, the ATP and the WTA – on Wednesday where they lost in straight sets 6-1, 7-5 to Omar Jasika and Bernard Tomic.

The 59-year-old and Sock were vastly outplayed by their Australian opponents, coming second in almost every statistical measure in their match in Newport, Rhode Island.

Ackman had been invited to play by Sock, who had received a wild card entry to the tournament, which is a WTA 125 event and also sits on the ATP Challenger Tour, a lower-tier men’s tour focused at giving younger or aspiring players an opportunity to progress their careers.

Ackman – the founder and CEO of Pershing Square Capital Management and has a personal net worth of $9.5 billion according to Forbes – said it was a dream come true to play pro tennis just once.

“I feel like maybe it’s one and done,” Ackman said afterwards, per The New York Times. “But I figured one, in my life, that seemed fair.”

On social media, Ackman called the whole experience “very humbling” and detailed the “stage fright” he felt playing on a professional stage.

“I can speak in front of an audience of a thousand people or in a TV studio on a broad range of topics without any preparation and without a twinge of fear, but yesterday I had my first real experience with stage fright,” Ackman wrote on X.

“I found myself on a tennis court in a live streamed professional tournament with a few hundred in the crowd. Throughout the match, my wrist, arm and body literally froze with the expected negative outcomes. I had difficulty breathing, and it was not a fitness issue. It got a bit better as the match progressed, but I was not able to overcome it.”

While his appearance ticks off a lifetime goal for Ackman, his foray into professional tennis was met with derision from fans of the sport, including journalists and former pros.

Former world No. 1 Andy Roddick was extremely critical, highlighting his own involvement in the International Tennis Hall of Fame and the organization’s role in the sport.

“Bill Ackman, who’s been a massive tennis fan, supporter, funds the PTPA (Professional Tennis Players Association), does the whole thing, wanted to play a pro tournament. So, there was obviously some exchange of something,” the 2003 US Open winner said on his “Served” podcast. “You don’t give a wild card to someone who 50 players at my club are better than.

“This was a total miss. Now, the job of the Hall of Fame is to preserve and celebrate excellence in our sport. This was the biggest joke I’ve ever watched in professional tennis.”

When contacted by CNN Sports, the ATP pointed to its rule on wild cards, saying tournaments “may not receive compensation and players may not offer compensation in exchange for the awarding of a wild card.”

CNN Sports has contacted Pershing Square Capital Management to offer Ackman the right of reply. CNN Sports has also reached out to Sock, the International Tennis Hall of Fame and the WTA for comment.

Roddick also called into question the effort levels of the players involved, apart from Ackman, saying that the match should be reviewed for its apparent lack of competitiveness.

“There was exactly one person on that court trying as hard as they could,” he said. “If you want to argue with me, go back and watch that video. And you can’t tell me there was more than one person trying as hard as they could every point, or any point. It was a disaster.”

On social media, Ackman wrote that the “competition were clearly holding back” which “made it even more difficult as I had too much time to think.”

CNN Sports has reached out to Jasika and Tomic via Tennis Australia for comment.

18-time grand slam singles champion Martina Navratilova weighed in on Ackman’s involvement, writing: “Apparently you can buy yourself a wild card. Oh to have the confidence…”

Tennis journalist Jon Wertheim also criticized the appearance of the hedge fund manager at the tournament, writing on X: “This would’ve been fine for a pro-am. For a sanctioned event with points and prize$? It was, at best, wildly inappropriate and lacking in integrity.”



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