ST. PAUL Minn. — It took two phone calls with his agent.

That’s it. Two.

When it came to a contract from the Minnesota Wild last summer, there were no lofty expectations from defenseman Jake Middleton, especially after spending six years mostly in the minors and finally getting his first full year in the NHL last season at the age of 26. There was no “Get me a big contract, Joey,” even after years of living paycheck to paycheck to afford Silicon Valley apartment prices on at times a $50,000 minor-league salary with San Jose Barracuda.

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“I remember that first AHL paycheck, when I saw the taxes they took out of it, I was like, ‘Oh boy, this is going to be a long year!’” Middleton said, laughing.

Over the years, Joe Resnick has negotiated some mega contracts for some mega talents like Joe Thornton, Rick Nash, Logan Couture, Adam Henrique and Jake Muzzin, but one of the most gratifying calls Resnick has ever made in the agent business was when he called Middleton last offseason to inform him he was about to go from bricklayer just a few years earlier to millionaire with one stroke of the pen.

“You work hard for all your clients, but Jake’s the type of guy you go the extra 100 miles for because he’s as honest as the day is long, there’s no nonsense with him, he’s a loyal kid and he’s just worked his butt off to get to this point,” Resnick said of Middleton, who was coming off a league minimum $750,000 contract. “Jake called me before free agency and said, ‘Rez, I’ve never made money, so let’s not get crazy.’ So when I made that phone call and told him we agreed to a three-year deal worth almost $2.5 million per season, that was one extremely emotional call for both of us.

“It wasn’t the biggest contract, but I felt so good about it.”

Middleton almost dropped the phone.

“I just said, ‘Send the papers before they change their mind. I’ll sign it,’” said Middleton, acquired for goalie Kaapo Kahkonen at last year’s trade deadline and stapled to captain Jared Spurgeon’s left side ever since. “I’ve had a friendship with Joe since I was 14 back to major bantam in Ontario, so he’s gone through all the hard stuff with me. For him to call me and say I got three years of security was pretty cool.”

And when he called his parents, Darlene and Steve?

“Now, that was emotional,” Middleton said, smiling and flashing his missing front teeth. “They cried instantly just because they really had to deal with all the pissed-off phone calls I would’ve had and FaceTimes and that type of thing throughout the years of maybe not getting an opportunity or not making the most of some opportunities I’ve gotten. So, after six years of pro, to be able to do that, they were excited, they were happy, they were emotional. It was just … gratifying. Just so grateful this has all happened.”

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Middleton knows the value of a dollar.

“They weren’t born with a silver spoon in their mouth,” Darlene said of her three children, Jake being in the middle. “He worked extremely hard to get where he is.”

Jake Middleton. (Courtesy of Darlene Middleton)

Born in Wainwright, Alberta — coincidentally teammate Mason Shaw’s tiny hometown — Middleton moved to Stratford, Ontario, at the age of eight. Stratford is a town of 30,000, has a hockey rink that opened in 1924, is full of cornfield and dairy farms and has a world-renowned Shakespearean Theater.

His parents owned the restaurant Honeypot in Wainwright, but as long as Middleton can remember in Ontario, his dad headed to work at 4 a.m. to do custodial work at a Toyota plant.

Now 67, Steve still works there. Darlene does sales and marketing for a company after doing the same thing for years at a local newspaper.

“My parents worked hard for everything,” Middleton said, beaming proudly. “Now that I’m older, I realize they had nothing, but we had everything. They just did everything for us, so it doesn’t feel like we didn’t have a lot of money. Growing up doesn’t feel like I didn’t have much because we really did. We always had skates, we always had sticks. We just had everything. And we were happy.”

Jake and his younger brother, Keaton, a 6-foot-6, 24-year-old defenseman for the Colorado Eagles, had jobs at a very young age.

When Middleton was 12, he and his brother scrubbed dishes at a local diner. They then worked for a used office furniture store. They’d help refurbish the furniture and resell the items. Middleton worked on a 60-acre hobby farm cutting grass and doing odd jobs like painting sheds and feeding goats. He couldn’t believe he was making $12 an hour for such fun work. But Middleton’s brother had a friend whose father owned a masonry. He offered to pay the brothers $15 an hour to lay brick and set up scaffolding because he had the contracts for a bunch of new subdivisions going up in Stratford.

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“So I had to tell the old man I couldn’t work on the hobby farm anymore,” Middleton said. “I felt bad. But three dollars more an hour! I had no choice.”

This was the Middleton brothers’ summer job for four years. The young hockey players would work out at 6 a.m., go to work at 8 a.m., then they’d skate at night and do it all over again the next day.

“And we got way more than minimum wage,” Middleton said, smiling. “By the end of it, I think I was getting 18, 19 bucks an hour. It was way better than doing dishes or any other odd jobs I was doing.”

Middleton worked as a bricklayer up until age 20 — the year before he turned pro and after captaining the Ottawa 67’s. In fact, even when hockey came to a halt in 2020 during the pandemic, Middleton went back to work at his buddy’s construction company. He built fences for six weeks despite being a four-year pro hockey player at that point.

Keaton and Jake Middleton. (Courtesy of Darlene Middleton)

“It was fun,” Middleton insisted. “This is what we were taught as youngsters. If you wanted your own fun money and that kind of thing, you’d work. That was just always instilled in us. Work for what you want. It was better to go and do something and make money doing it rather than sit around on the couch.

“It’s just how I grew up. We’ve had a job forever, so let’s just say, I wasn’t about to fight the Wild for a few more bucks.”


Middleton is one fascinating guy.

He’s simple and proud of it.

He famously rotates through five white T-shirts, five black T-shirts, three hoodies, a couple pairs of jeans and three jackets, and that hasn’t changed since he finally earned the big paycheck.

“I don’t like to think about that kind of stuff,” Middleton said. “When I’m waking up in the morning, it’s easy. The hardest part is finding a clean one. I’m not too flashy or into fashion.”

Wild coach Dean Evason calls him a “throwback.”

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Not only the way he plays — he’s big, skates well and is physical — but the way he is off the ice with the big mustache, the missing teeth, the Harley Davidsons he rides to and from practice and games (maybe not so much in the recent sub-zero temps, but over the summer, in training camp and early in the season) and the big, aviator sunglasses he sports all the time.

“It’s because of these big ears,” Middleton said over lunch earlier this season in St. Paul. “I wear the flat hat and big sunglasses because it looks more proportionate on my head.”

His teammates find him hilarious, well, except when he’s walking around the locker room basically completely naked. Under his uniform, he proudly wears nothing but cut-resistant socks and a jockstrap. Matt Dumba says he looks like he’s wearing “assless chaps,” and teammates hurry to get dressed or they’re liable to have a couple cheeks in their face.

Middleton terrorizing the locker room without a care in the world…he’s an icon.

— dont worry about it (@soleildabs) December 19, 2022

Middleton, who always conducts his Bally Sports North between-periods interviews shirtless, explains that, “I run hot. I get uncomfortable wearing a bunch of underwear and stuff. I like things looser and like to let everything breathe.”

After he was traded early in the morning to the Wild, he needed to wait for the malls to open in San Jose so he could buy some luggage. Before that, he traveled with a carry-on suitcase or threw stuff in trash bags.

Over the summer, he and his then-fiancée, Natalie, rented teammate Alex Goligoski’s downtown Minneapolis townhome. After signing the new contract, instead of a big house search, Middleton noticed the townhome directly across the street was on sale. He bought it.

“In California, I was making Nat live in 430 square feet because that’s basically all I could afford,” Middleton said. “It’s nice to have a home now.”

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Now, teammates Shaw and Connor Dewar live in Goligoski’s townhome. Natalie is a nurse in the cardiac stepdown ICU department of a downtown Minneapolis hospital. When she works late, Middleton heads over there and hangs out on their couch for a few hours.

“We’re 26 years old,” Middleton said of him and Natalie. “We got our dog, Leo, and no kids. Why would I want to move out of Minneapolis? This summer we went to First Avenue and Fine Line for like four or five concerts and ball games on the weekend. We’d buy a $10 ticket and go hang out in the upper deck at the Twins games. It’s just a 15-minute walk to everything. Spoon and Stable, Billy’s Sushi, the ham and cheese croissant at Bellecour (Bakery) is like butter and melts in your mouth. It’s perfect. Plus, I’ve got a garage for my toys.”

We’ll get to his toys in a moment because that’s about the only thing he’ll splurge on, but even Middleton’s wedding wasn’t extravagant.

Middleton married his high school sweetheart on July 15 in Nashville. Technically, they eloped, “but what better way to elope than to invite your parents and siblings?” Middleton said, laughing.

The couple plans to have a bigger celebration next summer in Stratford, but COVID-19 kept pushing their wedding plans back, so they decided to go to a courthouse and get the paperwork signed. And what better place to have a quick wedding celebration than Music City?

Jake and Natalie got married, then went to Jason Aldean’s Rooftop for a couple hours, had dinner at Twelve Thirty Club and ended their night singing and dancing away at Legends.

“We were staying in an Airbnb with my in-laws, but then I rented a hotel room for the purpose of, well, I just got married,” Middleton said, laughing. “It was only 12 of us between the two families, so it was nice because it wasn’t like when you’re at a giant wedding and you have to try to talk to everyone. It was really enjoyable.”

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Middleton owns three motorcycles and recently bought a fourth to surprise his dad as a gift for him.

(Courtesy of Darlene Middleton)

It’s a 2002 Heritage Springer Softail. But that’s not the first time Steve was surprised by his son with a purchased motorcycle.

For as long as Middleton can remember, his father has ridden motorcycles. Steve’s dad, Robert Bruce, was in World War II as a dispatch rider. He had tours in North Africa, France, Germany and England. In fact, Jake’s left arm has a sleeve full of tattoos to honor his family. There are war medallions to honor his grandfather and cardinals to honor his mom’s side of the family. Darlene’s mom told her before she passed away that cardinals would be how she would look over everyone.

A few years ago, Steve and Darlene drove to London, Ontario, to check out this 2002 Royalstar Venture. Darlene took a picture of Steve sitting on the bike and sent it to her two boys.

It cost $7,200.

“Twenty, 30 minutes later, Jacob sent a picture of a money order,” Steve said. “He had just signed his first NHL contract and said, ‘Go buy it.’ I’ve put about 75,000 kilometers on it.”

Of the three motorcycles he owns, his proudest possession is a Softail Cross Bones. Harley-Davidson only made four of them, “so that’s a little investment, I would say,” Middleton said. “I know it’s kinda dumb to have three motorcycles when you can only ride one at a time.”

(Courtesy of the Minnesota Wild)

But in California, Middleton loved nothing more in his time off than grabbing Natalie and heading up the Santa Cruz Mountains or heading to Monterey. In Minnesota, he’s already explored by going up north to Brainerd or east to Stillwater and up and down the St. Croix River.

“Nat just sits there, but it wouldn’t be as much fun without her,” Middleton said.


Making it to the NHL was a chore for Middleton.

Middleton is aware there are stars in the NHL and then there are role players, and he falls into the latter category. But as a kid growing up, he was one of the top prospects in Canada. He played in a bunch of showcases, was the eighth pick in the OHL draft and was ultimately traded from Owen Sound to Ottawa, where he was a terrific player.

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But he knew he wasn’t going to be a high pick in the 2014 draft, so he didn’t attend the draft in Philadelphia. Still, he never thought he’d be selected with the 210th and final pick in the draft by the Los Angeles Kings.

Middleton attended a Blue Jays game that day. He kept scrolling his phone and refreshing to see where he was selected. Pick after pick, round after round, his name never was announced. He was so angry, so stressed, so embarrassed, he actually threw his phone at one point. Finally, he got a text from his father that the Kings drafted him last in the entire draft.

“Better than nothing, I guess, but it wasn’t fun,” Middleton said.

“It still bothers us,” said Steve Middleton. “It’s hard to understand.”

Added Darlene, “You have no idea how hard he had to work for this, and we’ve plunged through it with him.”

Resnick was so worried that Middleton was going to slide through the draft that he agreed to an amateur tryout with the Florida Panthers in the sixth round if Middleton did not get drafted. The Kings drafted him but never offered him a contract. He went back in the 2016 draft and went unselected. The Sharks offered Middleton a tryout, then a two-year AHL deal. But he was told if he played well, they would convert it into an NHL deal. After that first year, the Sharks indeed signed Middleton to an entry-level deal.

But that first year in the AHL, Middleton lived on a mattress in the dining room of teammates Michael Brodzinski and Jonathon Martin’s two-bedroom apartment for $1,000 a month.

Steve said his son’s perseverance started at a young age when he first fell in love with hockey. At age 3 or 4, Jake asked his dad how to get well-conditioned.

“I said, ‘You need really good lungs,’” Steve said. “He said, ‘How do you do that?’ I said, ‘Jogging might help.’ And he proceeded to run 10 times around four blocks around our home day in and day out. We had to slow it down. And on the ice, we couldn’t stop him.”

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The Middletons always joke that Jake and Keaton are a set of twins, only two years apart. They have similar work ethics and “are the best friends you can ask for,” said Darlene.

“He’s two years younger, but two inches bigger and 30 pounds heavier,” Middleton said of his brother and former Barracuda teammate who just spent Christmas with his brother and wife in Minneapolis. “So I can’t fight him anymore because he wins. But he’s just like me. Every time he gets offered another deal, he’s like, ‘Alright, I get to play for another year and not get a real job!’”

Still, Jake has been dealing with adversity his entire life.

It started when his parents were so excited to sign up their then-5-year-old for youth hockey, they showed up at the rink and he had his heart broken because he was too young. He was bullied a lot as a kid, his parents said, because he always played up in age and the older kids didn’t want him there.

(Courtesy of Darlene Middleton)

Even as a pro, Middleton had to deal with humbling moments.

In 2018, the Sharks were holding Media Day, where players take pictures and videos that could be used in programs or the Jumbotron.

“As the process was going on, all of a sudden, it’s his turn in line,” Steve said. “He’s dressed, everybody’s there. Camera’s set up, they take the pictures of the guy in front of him and then the room just empties. The whole room empties. The team guys, the trainers are all gone. And then he’s standing there wondering ‘what’s going on?’ And then the guy runs back in and says, ‘Oh, you didn’t know? We’re not going to take your picture now. The Erik Karlsson trade just went through.’”

Added Darlene, “So all of a sudden, there was just Jacob alone in a room. He got undressed and called us very upset. He said, ‘I was just kind of forgotten about. It was brutal.’”

“Yeah,” said Steve, “It was a real throat punch. But he persevered, like usual.”

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Steve and Darlene say their son’s always been this way.

“I remember his grade eight graduation,” Darlene said. “We go and all of a sudden he’s playing bass guitar. He’s upfront and he did this to surprise us. We didn’t even know he could play guitar. I was proud as punch because he’s up there playing bass guitar like he’d been doing this forever.”

Added Steve, “You throw anything at that kid and he’ll pretty much get it mastered.”

Marcus Foligno, Middleton’s teammate in Minnesota, gets a kick at how easy-going Middleton is. He calls him, “No maintenance.”

“Just the mustache and how thick he is, it just goes so perfectly with that guy’s character,” Foligno said, “He is just so happy to be here. Money aside and term aside, when he signed that contract last summer, you’re now labeled as an NHL player. I think that’s one of the coolest things in the world is that you-made-it moment. He’s just a blue-collar, hardworking guy and earned his way here.”

Middleton feels the part now, which is why he was so disappointed when the Wild lost out in the first round last spring after a franchise-record 113-point season.

“It’s like an unfinished business feeling,” Middleton said. “I know I came in late, but the potential for what we could have done was exponential, and we just didn’t take advantage of it. So it does feel like (an) unfinished business-type scenario where we’d like to run it back and do even better.

“I am proud to be part of a team that wants me. I just have fun playing hockey. It was never work. It is never work. Obviously all those times it sucked getting cut at training camp, the ups and downs stink. But what else am I going to do? I don’t want to go do anything else. And you still get paid pretty good money to play American League hockey. So if you can make that last as long as you can, it’s still a good career. And I guess I just had to wait in line longer than most. But I kept waiting, and things worked out so far.”

(Top photo: Brace Hemmelgarn / USA Today)