Ed Kane Just Wants To Have Fun (Right?)

Inside the world of Boston’s King of the night.

Photo by Mona Miri

Boston. L.A. London. Bangkok. Ed Kane shows up in more places than James Bond during a double feature—and it’s hard to know where he’s going to turn up next. The first time we speak, over the phone, the local nightlife king is sitting by an infinity pool atop John Henry’s super-yacht off the coast of Miami. It is, after all, the only way to unwind after a day spent shopping alongside old-money art collectors and overnight crypto-millionaires at Art Basel. As we talk, I can hear the pool’s waterfall cascading in the background.

I was not surprised to learn that Kane, whose ever-present smile makes you feel like you just became best friends, was hanging out with his good pals the Henrys. Kane wears his connections to the Red Sox and Boston Globe owners on his sleeve. He keeps a John and Linda Pizzuti Henry bobblehead on his TV stand and hangs a large black-and-white photo of himself and the other groomsmen from the Henrys’ wedding in the kitchen of his Downtown Crossing home. Despite having never, himself, owned a sports franchise, Kane has ridden in three duck boat championship rallies and one double-decker victory parade through Liverpool, England, where Henry owns a soccer franchise, and has three Red Sox World Series rings inscribed with his name.

Make no mistake, the Henrys are far from the only boldface names who regularly ping Kane’s iPhone. Virtually every bigwig in New England, party animals and recluses alike, seems to be in near-constant contact with him. “I have a lot of billionaire friends,” says Kane, somehow sounding earnest. While not a billionaire himself, he owns Big Night Live at the Garden, Mémoire at Encore, the Grand in the Seaport, and some 17 other restaurants and nightclubs. He dines regularly with Robert Kraft. And because Kane wants to be liked, people want to like him right back. They offer him things. When, for instance, Kane suffered a medical emergency in Maine several years ago and needed immediate care, friend and auto magnate Herb Chambers dispatched his seven-seat helicopter to airlift Kane to Mass General. When COVID-19 hit, Kane went west, taking up TV producer and Sox chairman Tom Werner’s offer to ride out the early days of the pandemic in Werner’s Los Angeles abode. Last year Celtics owner Wyc Grousbeck tried to teach him guitar. “I think if you asked 20 people in town ‘Who’s your best friend?’ I’d say at least 10 of them, if not 15, might say, ‘Well, it might be Ed,’” says Grousbeck. “He’s best friends to a lot of guys.”

One of the advantages of having so many buddies—and such notable ones—is the business relationships. When Steve Wynn was looking to open a nightclub at his Boston casino, it was Kraft who vouched for Kane. When Kane wanted to build a nightclub at the Garden, John Henry helped set up a pivotal meeting with the company that owns it. Chambers, Kiss 108’s Matt Siegel, and the Wong family of Kowloon fame are among Kane’s investors.

On the other hand, one of the pitfalls of having so many fabulously wealthy friends, Kane tells me from Miami, is figuring out what to get them for the holidays. Kane had just bought himself an enormous silver print of a Japanese maple tree at Art Basel—and, noticing that his travel mate, Linda Pizzuti Henry, had her eye on it, he bought one just like it to give to her. “Merry Christmas!” he says, adding that the Henrys don’t expect him to buy them anything. Really, what they and most people want from Kane is not material at all. “They’re happy just to be friends and have fun,” he says.

Fun, after all, is precisely what Kane does. He offers it to the city’s twentysomethings, who pack the dance floors at any of his glamorous nightclubs every weekend. He provides it to the city’s pro athletes and their entourages in the form of VIP access to their favorite musicians and DJs when they perform at his venues. When Guy Fieri comes to town to check on his restaurants, it is up to his partner Kane to plan a weekend’s worth of nonstop amusement for the high-octane food celeb. And even though Kane won’t be spotted dancing on any leather couches at the Grand, he serves as a guide of sorts to his famous friends who are not so adept at letting their hair down. In some ways, it’s more accurate to think of Kane not so much as a nightclub owner but as a producer of fun for everyone.

When I finally make it out one night with Kane at Big Night Live, he leans against a railing and takes in the club scene, watching several hundred bodies writhing on the dance floor before us underneath pulsating lights and high-def LED screens. “I love to see people have a good time,” he says, grinning from ear to ear.

Knowing how to show people a good time, making people happy, and taking care of their needs has made Kane not just one of the most beloved Bostonians—it has made him successful, wealthy, and respected as the unofficial Czar of Boston Nightlife. But the question no one seems to be asking is whether the king of fun is having any of it for himself. “It’s like any other role,” Kane says of his life-of-the-party persona. “Part of the magic is that people need to believe in the man behind the curtain. Like the Wizard of Oz. They just have to believe in the story, too.”

From left, Linda Pizzuti Henry and John Henry, owners of the Boston Globe and the Red Sox, are some of Ed Kane’s closest friends. In fact, he introduced the two. / Photo by Jim Davis/The Boston Globe/Getty Images

It’s four hours until showtime when Kane arrives at Big Night Live on a Saturday. He was hoping to meet up with Chambers and Steve DiFillippo, owner of Davio’s, who dropped by to dine in the venue’s VIP green room overlooking the Zakim Bridge, but he’s too late. The car and restaurant titans have already eaten and been replaced at the table by Matt Barnes, the All-Star Red Sox pitcher, and his entourage, who are digging into bowls of chips and guacamole. Barnes is practically vibrating he’s so excited to see the night’s headliner, Dutch DJ duo W&W, whose hit “Bigfoot” has been Barnes’s walkout song for the past four seasons. “Thank you so much for having us,” Barnes tells Kane. No problem, Kane replies as he smiles and slips Barnes his business card. “They’re excited to see you, too.”

I’m feeling a tad starstruck, but not Kane. For him, it’s just another day at the office. After all, he points out, “I’ve been doing it for so long.”

There are many ironies running through Kane’s life, not the least of which is that from the time he was a kid, he swore he’d never make his living in the service industry. After all, he’d seen the business up close, growing up and working at his dad’s sports bar, Kane’s Place, across from the Fore River Shipyard in Quincy. He vowed to chart a different course for himself. He got excellent grades in high school in the North End and developed into a hell of a hockey player, eventually earning an academic scholarship to Harvard in 1983. After graduating, he wrangled a group of classmates together to launch a company that helped politicians on Beacon Hill navigate computers, which were new at the time. For six years, Kane and his company thrived. And that could have been the end of the story—until something unexpected happened.

In 1988, a regular patron at Kane’s Place tipped Kane’s dad off about a sleepy old breakfast joint languishing on prime shore-side real estate in Hingham that they might be able to buy. The opportunity and the lure of the family biz were more than Kane could resist, so he ditched the computer company and, along with his father and brother, Joe, bought the restaurant, gutted it, and turned it into Stars on Hingham Harbor. Three years later they opened the ritzy, high-ceilinged, and still wildly popular Tosca across the street. Then, on the heels of that success, they launched WaterWorks, a nightclub that soon became a South Shore favorite among pro athletes and financiers. In its heyday, the only place selling more beer was Fenway Park.

With the success of WaterWorks, a new nightlife king was born, albeit one still in his infancy. In 2006, Kane, his brother, and Randy Greenstein, the bombastic Kiss 108 radio personality who’d worked as WaterWorks’ house DJ, formed Big Night Entertainment Group. Their initial plan was to capitalize on their ability to throw epic ragers for big liquor brands.

At the time, hospitality icon Patrick Lyons reigned supreme over Boston nightlife. He gave Kane his first big shot in the city: a tired old nightclub located in the Alley called the Big Easy, which had fallen on hard times (snarky college kids called it “the Big Cheesy”) and needed a youthful but elegant makeover. Big Night took the reins of the club and bet big that finance bros, some college students, and other moneyed New Bostonians would pay whatever was asked to get past the velvet ropes—even in a town that wasn’t exactly a nightlife hot spot—if they gave the place enough swagger. Kane renamed the club Estate, invested $250,000 into renovations and sound equipment, booked the hottest new celebrity DJs, and charged top dollar for VIP bottle service. And it worked. “He saw what was happening in the most prized tourist cities around the world, and then he brought that to Boston,” says Seth Greenberg, Boston’s nightclub kahuna emeritus of the ’90s and early 2000s. “He’s the trailblazer.”

As with many empires, expansion started slowly but has since taken on warp speed. First came a call from Foxwoods casino, which wanted Big Night to design and run its marquee 21,000-square-foot nightclub, Shrine, along with an enormous Mexican-fusion restaurant dubbed Scorpion Bar. The casino gave Kane the keys to the kingdom once again when he suggested that an underused Foxwoods ballroom would make a terrific luxury bowling alley, and the nightspot High Rollers was born. Through relationships at the casino, Kane met fellow entrepreneur Fieri and together they opened Guy Fieri’s Foxwoods Kitchen & Bar just off the gaming floor.

Soon, Big Night had a small army of power players—from old-money Harvard chums to local celebrities and hospitality titans—chucking cash at anything Kane could dream up, and Big Night was gobbling up the most desirable real estate in town. In the past five years alone, Kane opened the Grand on Seaport Boulevard for the stupefying price tag of $14 million. Another $10 million was spent on Mémoire, the high-roller-friendly club inside the Encore casino. His most recent venture, Big Night Live in the Hub on Causeway at TD Garden, cost a cool $30 million and brought the total number of clubs and restaurants his group owns to 17. In 2021, a time of shattered dreams for many in the hospitality business, Big Night was pulling in revenue faster than ever.

Despite his success, Kane is a far cry from the Old World image of a cigar-chomping, wheeling-and-dealing nightclub impresario. He is cheery, athletic, and, by all accounts, ethical. Even though he sells more beer and liquor than just about anyone in New England, Kane has never been a heavy drinker and recently stopped tippling altogether. “A lot of club owners, you only see them after midnight, and you don’t know what else is going on in their life, and there’s all kinds of baggage,” says filmmaker, author, and celebrity chef Eddie Huang. “Ed doesn’t have that. I think it would be safe to say that the stereotype of club owners is that they’re raging cokeheads, and Ed couldn’t be further from that.” What Kane likes most about nightclubs is not going to them, but rather coming up with the concepts and designing them. “I’m a design guy first,” he says. “And I’m an experiential guy. So yeah, I’ve been to a million nightclubs. But I’m not a nightclub guy.”

For his own fun—at least when he’s in Boston—Kane likes to make sure he’s creating fun for others, even when he doesn’t partake. “His thing is, he’ll get the party going at one of his venues and he’ll get everybody there. He loves to host,” says Kane’s college friend Jeff Lawrence. “He’ll stay and talk for a while. And then, as the night goes on, all of a sudden you look around and he’s gone. He makes this mysterious exit. He just kind of disappears.”

Ed Kane owns 20 clubs and restaurants, including some of the hottest spots in town, such as the Grand in the Seaport, Big Night Live at the Garden, and Mémoire at Encore. / Photo by Mona Miri

On a Tuesday night, I find myself with Kane in a decidedly different setting: the Cantab Lounge, a newly renovated dive bar where Patriots Kendrick Bourne and Devin McCourty, along with a bevy of donors, have shown up for an invite-only Big Brothers Big Sisters fundraiser. Kane is not here to schmooze but rather to support a friend: Tonight, pal Wyc Grousbeck’s rock ’n’ roll cover band is set to play. As we make our way toward the stage, Kane takes out his iPhone and dials someone on FaceTime. Grousbeck’s wife, Emilia Fazzalari, flashes up on the screen. It turns out she’s stuck at home working so Kane wanted to surprise her with a front-row seat. With her face on his screen, the band busts out the first couple notes of “Honky Tonk Women” and Kane sways back and forth, beaming with all the energy of a supportive parent at a soccer game. “That is Ed,” Fazzalari tells me later. “It was so thoughtful, and so sweet. And so adorable, because I could see Wyc playing, and I could also see Ed’s thumbs up on the screen.”

Aside from these typical considerate flourishes, Kane’s trick, if you can even call it that, is to offer people—some of them with a net worth 100 times his own—things they don’t already have, be they new experiences or even companionship. And he always knows how to nudge them out of their comfort zones and get the party started, whether he’s leaping from a 50-foot cliff off the Amalfi Coast or goading nervous executives into hopping onto the back of his motorcycle to tear up California’s Pacific Coast Highway.

The most famous example, of course, is his years-long bromance with John Henry, which dates back to the mid-2000s. The two hit it off and spent what they describe as 100 straight nights on the town together. “As hard as he works, he works hard at having fun,” Henry says. “A lot of successful people aren’t very good at that.” In 2007, Kane helped introduce a sheepish Henry to Linda Pizzuti because Henry couldn’t work up the gumption to talk to her. The couple has been married since 2009.

Tom Werner, who recently got engaged, spent many of his bachelor years with Kane and the pre-married Henry, along with a group of other successful Bostonians of a certain age who called themselves the Cirque du Rire, or the Circus of Laughs. They consider those days at Kane’s side not just as a rollicking blast but as an education in how to be cool. “I think Ed probably is more experienced and sophisticated in relationships with the opposite sex than John or me,” Werner says. “So he was a mentor of sorts.”

Kane even looks the part of the nightclub guy, right down to his sartorial choices, which skew way younger than his buddies’. He wears the latest streetwear trends, be they sneakers designed by Virgil Abloh’s Off-White, or hoodies with the cartoon heart logo of Comme Des Garçons, beloved by singer Frank Ocean, that translates to “like the boys.”

One night, I joined Kane at Big Night Live and, for a while, it was just the two of us and a bottle-service girl dressed in a scanty Mrs. Claus costume sitting at his owner’s table. I stepped away for a minute, navigating past a bouncer to the club’s VIP bathrooms, and when I returned, a half dozen stunning twentysomething women in glittering cocktail dresses had materialized, all part of a fun-loving group chat of clubgoers Kane calls “the Squad,” with Kane sitting in the middle. “Women all want to meet the owner,” Kane tells me. “You have no idea how many DMs I get asking me out. And I’m 60!”

Another irony in Kane’s life is that while his friends sought advice and confidence from him when it came to affairs of the heart as though he were Don Juan reborn, Kane—in his skinny jeans—is still single. There’s also the fact that while being a nightclub owner can be a great way to meet women—and introduce them to your friends—it makes it hard to settle down in a relationship. Running a nightlife empire means lots of work at all the wrong hours. And sometimes, Kane says, women seem to want him for all the wrong reasons. “There are plenty of women who want you to spend money on them, or take them on trips, or buy them things, or get free access to the club,” he says. “There’s an endless supply of that, but that’s not really what I want, you know?”

Kane was married once and is now divorced. He is co-parent to his beloved three-year-old daughter, whose mother, a former girlfriend, remains a close friend. But he is still very much an eligible bachelor. Two of his friends tell me they think Kane may well be a commitment-phobe. And despite all that mentoring to his friends, he has trouble approaching women himself. “I’m bashful around women, especially if I like them,” he says, adding, “I’m just awkward.” He says that he’d like to fall in love but isn’t all that focused on settling down. At least not yet. “Men as they get closer to 70 are like, ‘I better find someone now because I don’t want to be alone,’” he says. “And I’m always like, ‘I’m used to being alone.’ I sometimes prefer it.”

One afternoon, a few days after our night at the club, my phone buzzes and it’s Kane calling me on FaceTime. He’s visiting his New Hampshire home, which sits on 65 acres atop a mountain, and wants to show me the view. He flips the camera around and points it out his living room window. I recognize the familiar contours of Mount Washington, covered in snow, looming in the distance. I also see what appears to be thousands of acres of pristine wilderness. There are no signs of human life. There is only silence.

Not to state the obvious, but this isn’t exactly Kane’s typical habitat—inside a thumping, jam-packed club where everyone wants to talk to him. Instead, the solace of his mountain lair is “a better pace for me,” Kane says. “I’m quieter and more private than you think I am.”

Kane’s life in Boston, he explains, is kind of like being in a show. “You have to perform,” he says. “There are a lot of nights we have an event, or a client is coming, or just like whenever anyone I know comes in from out of town and they’re like, ‘Hey, I’m going to be in Friday and Saturday night, I’d love to see you.’ And you’re like, Oh, my God, really? There are moments where you can’t say no, you have to show up, you have to drag yourself out of bed, go out, and then you have to be on top of your game, and you have to be happy.” Looking out the window with me on FaceTime, he adds, “Here, I don’t really have to do anything.”

I was curious about Kane’s need to feel, as he said, “on top of your game” and always “happy.” So I asked YuChan Chu, the mother of his daughter, whom he sees each day. Surely, if anyone has caught a glimpse of Kane unhappy and not having fun, it would be her.

“Have you ever seen him sad?” I asked.

“Probably only twice in my life have I seen him sad,” she said, following a long pause. One time, she said, was after Kane’s father died, and the other was after a close friend died. Otherwise, “His game face is built in,” she tells me. “He is always happy. I think there’s probably some times when he’s not having the best day but he just looks like he’s having the best day. We all know not everyone’s going to be happy 24/7, but Ed hides it very well.” No wonder he loves to get away from it all. All alone in the wilderness, no one can see you frown.

New Hampshire isn’t Kane’s only escape. Before the pandemic, he traveled the world some 200 days a year, sometimes with friends, sometimes alone. He’d take off to Asia, and spend weeks on spiritual quests through the jungle, where he became, in his own words, a fake Buddhist. Or he would take off on his motorcycle up the California coastline.

When Kane talks about his travels, especially his solo adventures, it is tempting to think he might just ride off into the sunset one day and leave everything he’s built behind. Yet in most respects, he remains as dedicated and driven as ever and appears nowhere close to done. For Kane, as the famous song goes, the road goes on forever and the party never ends. “I always tell people he’s a shark,” says Kane’s brother, Joe. “Guys like him, it’s a different DNA. They get up in the morning and they don’t stop swimming until physically exhausted, done. They just keep on going.”

Kane’s next plan is to partner with Wynn Resorts on a new venue on a piece of land near the Encore that the casino company is hoping to develop. That project is on momentary hold, but when it—or some other exciting, tasteful, and extremely cool new Kane venue—does open, you will find the man himself, the producer of fun, in the owner’s booth dressed in the latest streetwear. And wearing a smile.