Twenty years ago today, April 18, Wayne Gretzky played his final NHL game, picking up an assist for the New York Rangers in a loss to the Pittsburgh Penguins in Madison Square Garden. The event was punctuated by tributes from the likes of Gretzky’s hockey hero, Gordie Howe, basketball legend Michael Jordan and a rendition of “Oh Canada” by Bryan Adams, who changed a lyric to pay tribute to number 99. But the Great One, 58, hasn’t exactly been resting on his hockey laurels in the years since. To mark the anniversary of Gretzky hanging up his skates, we look back on our 2016 cover story with the legend, where he discusses grand-parenting, other business ventures and the highlights of life after hockey.

Wayne Gretzky offered me a coffee. I declined but I should have taken it if for no other reason than to discover first-hand if the legend of the “Gretzky coffee” holds any merit. According to my sources (the internet), the Gretzky coffee contains nine creams and nine sugars—get it, 99?—and can be purchased off a secret menu at Tim Hortons. I believe they even call the ambulance for you while they pack your Timbits to go. No one knows if the order is inspired by the 55-year-old’s own preferred brew or if it’s some perverse product of Canadiana gone horribly wrong—like snowstorms in June, or Nickelback. Even Buzzfeed reported on the “Gretzky coffee” and, as you know, it is the internet’s listicle of record.

Anyway, I regretted the coffee decision for the rest of the day. This is what I think about when face to face with the greatest hockey player who ever lived in the lounge of a Toronto hotel, discussing his new fashion line, the No. 99 Wayne Gretzky Collection. Unlike most Canadians I grew up a fan of baseball rather than hockey, despite being drilled in the face by a fastball when I was 10. I’d obviously heard of Wayne Gretzky and respected his accomplishments, but I thought baseball was more engrossing. However, in my youth I also thought it was fashionable to tuck my turtlenecks into my pants in hopes of attracting a date. Neither of these facts—baseball fan or turtleneck tucker—qualified me to conduct this interview. Or, as it turned out, to attract a date.

In Toronto, though, it’s easy enough to get a feel for The Great One—and not just when you’re sitting across a table from him, side-eyeing his mug as he sips his coffee. Call it the Gretzky Experience, which starts with his Canadian Walk of Fame plaque on King Street West, immortalized in the concrete in front of the Princess of Wales Theatre, next to, believe it or not, a Tim Hortons! Coincidence? You decide.

A short jaunt westbound and you’ll find Wayne Gretzky’s Toronto sports bar conveniently located at, you guessed it, 99 Blue Jays Way. Seriously, who is this guy’s real estate agent?

The bar’s drinks menu includes a selection from Wayne Gretzky Estates Winery. I ask the bartender for a recommendation and she suggests the Pinot Grigio or the Merlot. I opt for the former—a chilled but dry vino with an aftertaste that hangs around like Gretzky parked behind an opponent’s net. I sip and take in the place, including the Stanley Cup itself sitting right there on the bar. It looks so different when you see it up close. I had no idea it was made out of shredded Red Bull cans.

Then there are the displays dedicated to No. 99 hockey memorabilia, from vintage jerseys to skates to sticks. Seeing these old battle-weary artifacts of the sport’s history makes me wonder—how does a former hockey star get into the fashion trade? I mean, I could understand a polo player or even a croquet star—you’ve seen the adorable cardigans they wear—but hockey?

“There’s probably two things that go with being an NHL hockey player,” Gretzky explains. My guess is mullets and toothless grins. I am, evidently, wrong. “Dress fashionable and play golf,” he continues, “because there’s peer pressure from the other guys on your team to dress half decent and participate in charity golf tournaments.” This explains why I’m confronted with so many sleek-looking Gretzky golf shirts at Sears, with tags boasting of cooling properties and “reflective features.”

Not knowing what to expect, I was actually pleasantly surprised. The golf shirts were light, the sweaters cosy and the jeans soft, with the most expensive items on hand ringing in at less than $80. I didn’t find any turtlenecks in the collection—maybe next season, Wayne?—but it seems Gretzky hit his goals of affordability, comfort and style. He notes that he was actually really nervous when he attended Toronto’s Fashion Week late last year to debut the collection. “At least when I went to a hockey game, I knew what to expect…[Here] I didn’t have any clue.” After all, in the fashion world the only creases are in the pants, and a hat trick is a cocked chapeau—perhaps a fedora, or a pork pie. Still, his collection played to an enthusiastic crowd that came out to see both the clothes and the man. The threads, as it turned out, proved a lot easier to spot than the guy whose name was stitched into them. The fashion arena proved so foreign that Gretzky didn’t indulge the crowd with the customary designer’s victory lap down the runway at the end of the show. Whether it was hockey team humility or just really comfy chairs, Gretzky remained in his front row seat, offering nary a wave. In hindsight, some may have even forgotten that he was there—kind of like his stint with the St. Louis Blues.

Still, as with his winery, bar and charitable cause, the Wayne Gretzky Foundation, which helps less fortunate kids play hockey, it looks like the clothing line is destined for success, despite Sears’ struggles in the tumultuous Canadian retail landscape. The department store chain closed a number of stores in recent years, including the prestigious Toronto Eaton Centre location, but they still enjoy a broad reach thanks to multiple suburban locales and an extensive catalogue business that allows hockey fans everywhere to shop The Great One’s line. And like on the ice, Gretzky isn’t working alone, with his business partners taking on the day-to-day operations of his various companies.

“There’s nothing in my life that I can do that’s going to give me that same high of lifting the Stanley Cup. But…when the clothing line is doing well or when a new wine comes out and wins a gold medal for something, you go, ‘Wow, that’s pretty cool.'”

This Charmed Life

It’s a charmed life, to be sure, enjoying the fruits of what being the best at slapping a little black puck into a net gets you. Gretzky, the pride of Brantford, Ont., moved to Los Angeles in 1988 after being traded from the Edmonton Oilers to the L.A. Kings—a deal that had Canadians sobbing into their Beaver Tails. To say that The Great One took to California would be an understatement. From the moment he stepped on the ice in Los Angeles he became the most fiercely loved Canuck in Hollywood since William Shatner slapped on a skintight space suit and commanded Scotty to beam him up. And Gretzky clearly enjoys life in La-La Land. It’s where he met American actor Janet Jones, of The Flamingo Kid fame, on the set of the variety show Dance Fever in the early 1980s. A few years later the sports hero and the screen star reconnected after a chance meeting in the city. Though they eventually put down roots in Los Angeles, in 1988 they married in Edmonton—the closest Canada ever got to a royal wedding—which could, in part, explain their longevity. Edmonton weddings have far higher success rates than Hollywood ones. The couple have five children—Paulina, who turns 28 in December, Ty, 26, Trevor, 24, Tristan, 16, and Emma, 13—but still manage to let loose, like in 2014 when they hit the town after walking the red carpet with two of their kids for the Toronto International Film Festival screening of the James Franco film The Sound and the Fury, in which Janet starred.

True, there are trade-offs to living in Los Angeles. For example, L.A. just doesn’t offer that authentic teeth-chattering, “I can’t feel my fingers” winter experience we Canadians adore. And once you go Hollywood, you instantly open your life to persistent public scrutiny.

Gretzky’s playing career came and went before the social media age, but his retirement lands smack dab in the middle of it. While Wayne himself isn’t exactly a prolific online presence, other members of the Gretzky clan tend to attract Instagram attention. In August, Janet sparked cries of insensitivity to cultural appropriation when she posted on Instagram photos of daughter Emma and her friends wearing Native American headdresses. And, you may recall, a few years back Paulina Gretzky had jaws dropping thanks to what she wasn’t wearing on Twitter—namely, clothes. Tabloids reported that the scantily clad Paulina even provoked the ire of her famous father, prompting a temporary disappearance from her online accounts.

Social media, though, also offers glimpses into the heartfelt familial moments, from vacations to the Gretzky kids’ own sporting aspirations. Ty, like his father, tried his hand at hockey while Trevor pursues a career in Major League baseball and Emma competes in tennis tournaments. And about a year and a half ago, Paulina and her fiancée, 2016 U.S. Open golf champion Dustin Johnson—who, in any other family, would be the elite athlete at the dinner table—made Wayne and Janet grandparents for the first time with the birth of Tatum Gretzky Johnson.

Photos and videos of Tatum abound on Janet’s Instagram feed, showing the little one following The Great One around the grocery store with a baby-sized shopping cart, or Wayne teaching Tatum to stickhandle using mini hockey sticks in much the same way Wayne played hockey, using toy sticks, with his own grandmother in her home as a child.

“Parenting and grandparenting to me are basically the same. You have the same love for your grandchild as you do your children. I think the biggest thing of all is to have that unconditional love for your children, which you naturally have,” Gretzky says, noting he and Janet babysit Tatum when his parents are away at golf tournaments. “We’d keep him forever if we could. It’s really been joyful. We love it.”

The Family Patriarch

Photo: Tobin Grimshaw

On the opposite end of the age spectrum, there’s the family patriarch, Walter. Not far from Gretzky’s Toronto bar resides the last stop on the Gretzky Experience, the Hockey Hall of Fame, an institution that Wayne may not even belong to had it not been for Canada’s Hockey Dad. It’s clear just how much Gretzky reveres his father, whom he dotes on at public events and joked playfully with at the Zoomer cover shoot, even grabbing the camera and taking photos of both him and son Ty. At 77 years of age, a stroke survivor and battling Parkinson’s disease, Walter continues to inspire younger generations. Aside from enjoying time with his grandchildren and great-grandson, he still visits community hockey rinks and even picks up disabled children every Sunday and brings them to church.

“My father has been such a great role model for so many kids,” Glen Gretzky, Wayne’s brother, says, citing Walter’s “encouraging messages” as the inspiration for his new kids’ book, Great, in which Coach Wally helps a struggling child learn to play hockey alongside the team’s superstar player, who suspiciously sports blond locks and the number 99 on his jersey.

“He’s a remarkable person and he’s doing really well. I think some days are hard for him [since] my mother passed,” Wayne, whose mother Phyllis passed away from lung cancer in 2005 at age 64, adds. “I know there [are] times where he…wished that my mother was there for him. But he gets around pretty good and still likes going to Leaf games and getting out, and people love seeing him.”

Walter is a picture of endurance and positivity, which gets me thinking about Wayne and his legacy. With the passing of his hockey hero, Gordie Howe, in June, Gretzky became the sport’s greatest living legend and ambassador—although hockey fans of a certain generation might argue that Bobby Orr deserves that mantle. In fact, in 1998, when he was named the greatest player ever by The Hockey News, Gretzky himself declared that either Howe or Orr deserved the honour. Gretzky, though, admits to me that he misses the game. However, if age 55 is really the new 35, I bet The Great One could actually still have a few more productive years on the ice. Just imagine the possibilities—Gretzky’s triumphant comeback season, where he faces off one-on-one against the likes of Sidney Crosby or Alexander Ovechkin or—

“No, no, no, I don’t miss it that way.”

All right then. Never mind.

“I literally skate once a year,” he says, perhaps referring to when he laces up for the annual Wayne Gretzky Fantasy Camp in Las Vegas, whose proceeds go to charity. “I don’t play a lot. Once you retire from the greatest sport in the world, the best players in the world, it’s tough to go and play pickup hockey. And, of course, I’m not very good any more either.”

Of course, Gretzky’s “not very good” is likely still better than most. Nevertheless, it looks like he’s opting for the Hollywood ending—riding off into the California sunset and spending time with family—which, admittedly, is far better than the Edmonton ending, which involves rousing the family in the dead of winter to help dig the house out from under 10 feet of snow.

As our time winds down, The Great One shakes my hand and says goodbye before heading across the lounge to grab another coffee. I’m torn here, weighing my temptation to follow him and see how he takes his java with my desire to not be labelled as “that creepy guy hiding in a potted plant spying on Wayne Gretzky.”I decide to leave and let No. 99 enjoy his coffee in peace. I don’t want to intrude. Besides, if his coffee habits are worth noting, I’m sure they’ll eventually pop up on Instagram.

A version of this article appeared in the October 2016 issue with the headline, “Wayne’s World,” p. 40-45.