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Even though it's the name of his newest venture, Nick Di Donato has yet to get a tattoo. Permanence is not typically associated with his line of work. But making a permanent mark is not so farfetched for someone whose company, the Liberty Entertainment Group, oversees some of the most frequented event spaces in town.

On busy nights, there may be as many as 15,000 people spread out across his diverse portfolio, including the Phoenix for concerts, the Rosewater Supper Club for elegant dining, or the Liberty Grand for a blowout party. Now that the Kiwanis Club has made Liberty Entertainment Group its official caterer for Casa Loma, don't be surprised if the castle, still in disrepair, becomes enormously desirable as a historic banquet hall (or haute frat house) in 2008.

His gift for spotting concepts that may seem derivative to globetrotters but register as new to Torontonians, is what has put him on the map. "Our success has always been based on being the first with a new idea," says Mr. Di Donato. "I'm very cognizant of the fact that you can't just do what the demand is; you always have to look for the need. What would people want to be doing and how do you get them there?"

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He is seemingly the man with the Midas touch, starting 20 years ago with sports bar P.M. Toronto, and today owning 14 properties, and involved in everything from LuminaTO to the Toronto International Film Festival.

At 49, he might be content to sit back and run his empire. But he is now embarking on his latest great Toronto venture: Partnering with club king Charles Khabouth, which is akin to rival rappers Kanye West and 50 Cent recording an album together, minus the verbal jousting. It's as much symbolic as strategic.

Their combined expertise in catering and live concerts means that there are limitless ways to influence the city's nightlife.

Last week, Tattoo Rock Parlour - on Queen Street West near Bathurst - became the first of Mr. Di Donato's and Mr. Khabouth's collaborations to open and occupies the footprint of one-time resto-lounge Left Bank. Designed by 3rd Uncle, the $2-million two-storey space bears the sophisticated stamp of Mr. Khabouth, whose decadent destinations for debauchery include Ultra Supper Club and the Guvernment/Kool Haus.

The layout is functionally deluxe: At front and rear, there are imposing black bar stations with backlit graphics that burst forth from illuminated bottles and a hanging perimeter of fringe that gives a cave-like feel. The wall closest to the entrance boasts a platform of undulating red leather banquettes, which have an unobstructed view of the stage. There are plenty of relic-looking details, from a table circa Tudor England to a frighteningly beautiful surgeon's lamp suspended above a dentist's chair where people can get tattoos, care of Blackline Studios, late into the night.

Sightlines are key, not just to ogle who's schmoozing with who - Tie Domi and Kelly Carlson (Kimber Henry from Nip/Tuck) - but to appreciate the live concerts (Dragonette will be performing on New Year's Eve).

"Nick and I had always joked that we'd do something together," says Mr. Khabouth, 45, from his Queens Quay office (coincidentally, his company name is Ink). "For us, it was always good competition, not dirty competition." He points out that it's a marriage of equals. "We're both established financially and I feel comfortable saying that. When one partner is money hungry, it creates a different atmosphere," he says. "We're very much in the same place in our lives."

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In other words, they are fathers (both with two children) who try to invest as much time in their families as their businesses. They also travel to get inspired. Mr. Di Donato not only has a second home in Miami but he says he has a new appreciation of Toronto after visiting South Africa and India.

This, along with the undeniable success of Asian-influenced resto-lounges Buddakan, Spice Market, Tao and Buddha Bar in Manhattan, Paris and Philadelphia, is how they arrived at Spice Route, the 8,000-square-foot oasis of Indian and Far East flavour scheduled to open in February. With a 150-seat outdoor terrace and an exotic-minimalist design - care of Mr. Di Donato's wife, Nadia, whom he entrusts with creating wow-factor environments - few people will remember that the building once housed the failed King Street West boite, Touch Lounge.

Understanding how a niche trend can work for a mainstream market and executing it with the highest standards is what's made Mr. Di Donato top of the Toronto heap: Other global cities may have their restaurateurs, impresarios and hoteliers, but Mr. Di Donato is a rare renaissance man.

It may come as no surprise, then, that he was raised in the restaurant business. His parents owned a restaurant called Lorenzo's that was expropriated to build the Eaton Centre. Discouraged from following in their footsteps, he graduated with an engineering degree from the University of Toronto and worked for Imperial Oil.

The day job left him antsy at night. "Getting up at 7 a.m. to go to the office and being there all day long and waiting to go home to have dinner and sit on a couch was just not my lifestyle," he says.

So in 1986, he and his older brother Pat (currently the Liberty Group's executive vice-president) opened P.M. Toronto, a sports bar near Maple Leaf Gardens. At that time, neighbourhood watering holes did not feature pool tables and projection screens. Not only did he attract the fans, he got the players coming in for a round after their game.

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Next came Club Max, an industrial-style nightspot for up to 1,100 people that took its cue from the edgy New York scene.

In the midst of concurrently launching the Phoenix, Joker and the Left Bank, he decided to do something decidedly more upscale. In 1996, he opened the Rosewater Supper Club, an airy, glamorous setting complete with private dining rooms, which made it a destination for celebrities and small, lavish, corporate parties.

Mr. Di Donato says there's no limit to how big he can get. "The reality is that once you put the infrastructure into place and you're not micromanaging, you're able to grow," he says. "The only challenge is the amount of time you have to give to each location, because if you ignore them, they can turn sideways."

Casa Loma is a prize property, but, for the moment, the Liberty Group simply supplies food and beverage. Some of the city's most important connectors got a taste of its potential following the film festival, when Entertainment Tonight Canada created a four-night "Studio Lounge."

"It had the class and elegance that we wanted to bring to the ET brand. The size and the scale and the glamour [were]perfect," says the show's executive producer, Zev Shalev, who adds that Mr. Di Donato approached him, wanting "to put Casa Loma on the map."

"There really isn't anything he can't do," Mr. Shalev continues from his Toronto office. "It's been nothing but a pleasure working with him."

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How the success of the Studio Lounge translates into a permanent venue that's open to the public has yet to be determined, as the Kiwanis Club is also in the midst of negotiating its next 20-year contract with the city.

But Richard Wozenilek, chairman of the board of trustees for Casa Loma, is not worried about Mr. Di Donato's respect for the property. Nor have any of the previous events been met with resistance from neighbours. "We send out a notice to the community adjacent to the castle to let them know, but we have a good friendship with them."

Mr. Wozenilek commends Mr. Di Donato for his "unbridled enthusiasm" and says he "really takes an innovative approach to events in the city."

And since Fashion Week has outgrown the Liberty Grand, moving into tents at Nathan Phillips Square, à la New York, Fashion Design Council of Canada president Robin Kay thinks that Casa Loma might be an interesting option for an off-site event during the Fall '08 shows held in March.

Ms. Kay says she might as well be "a billboard for Nick," given his ongoing support. "He has never, ever let me down."

Aside from this unofficial fan club, what distinguishes Mr. Di Donato from his contemporaries is his belief that Toronto has the potential to be an alpha city on par with Paris, London or New York, provided that there are enough exciting reasons for tourists to come once and return often. To that end, he also sits on Mayor David Miller's economic advisory committee, which suggests that he's committed to the long-term viability of the entertainment industry.

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"Let's face it," he says, "people who don't live here will usually report back to other people about the cultural activities and the sports activities. That's what puts a city on the world map."

For all the allure of establishing a brand internationally, Mr. Di Donato seems to prefer building his empire in Toronto. Here, he has a lock on the market. His biggest challenge is to continue to please all parties - from city council to his 800-plus employees - without being passed off as a self-serving entrepreneur who caters to the city's VIPs.

But it's hard to fault a man who leaves the opening of his club to attend his son's hockey game in Hamilton and still loops back by midnight to greet long-time clients. Describing himself as a construction guy at heart, he and his wife Nadia (who he met at a nightclub) live on the Kingsway and go out for sushi. His sons, 14 and 17, attend his alma mater, St. Michael's College School. The elder just found out he got accepted to the University of Miami's premed program.

Speaking of kids, Mr. Khabouth is preparing to be inked with his children's names, Mya and Charlie. Mr. Di Donato needs more coaxing. But certainly the thought must have crossed his mind? "I've thought about getting 'liberty' across my arm," he finally confesses. "It's not one of those tattoos you get tired of. One day, who knows, my company won't be around any more - but 'liberty' will still work."

But it's hard to imagine Mr. Di Donato no longer working. For him, the Liberty Entertainment Group is a pursuit of happiness.

The pleasure domes of Nick Di Donato

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No other company offers the same crossover experiences, from high-end dining to hard rock concerts.

1. PHOENIX CONCERT THEATRE

410 Sherbourne St.

2. LIBERTY GRAND

ENTERTAINMENT COMPLEX

25 British Columbia Rd.,

Exhibition Place

3. COURTHOUSE

57 Adelaide St. E.

4. ROSEWATER SUPPER CLUB

19 Toronto St.

5. CASA LOMA

1 Austin Terrace

6. C LOUNGE

456 Wellington St. W.

7. VELVET UNDERGROUND

510 Queen St. W.

8. SPLASH AT HARBOURFRONT,

LAKESIDE EATS, CREPE DU SOLEIL

235 Queens Quay W.

9. TATTOO ROCK PARLOUR

567 Queen St. W.

10. SPICE ROUTE (opening 2008)

499 King St. W.

All this and Fort York too?

One major project in Nick Di Donato's future involves a serious but celebratory nod to the past. Over the next four years, he will be involved in planning Toronto's bicentennial commemoration of the War of 1812. The year-long series of events will pay particular attention to the major revitalization of the historic Fort York site, which will include building a new residential community and Discovery Centre. Mr. Di Donato's track record for bringing new life to heritage buildings will certainly be beneficial to the committee, chaired by Deputy Mayor Joe Pantalone, as it seeks to attract tourists in non-traditional ways.

Amy Verner

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