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Bruce Dowbiggin

RIP Rob Bennett: The Promoter, The Pirate, My Pal

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16 minute read

Robert Bennett: 1952-2023

This is a column I hoped I’d never have to write. But my best friend Rob Bennett has lost his fight with ALS. And my life has a void that can’t be filled. Most people know Rob as one of the country’s top music promoters for more than 35 years. From James Taylor to Robin Williams to Raffi my pal knew them all. One night he even threw snowballs with Bruce Springsteen atop Mount Royal .

My own memories of the man are more personal. We met as U of Toronto students working the 1974 Christmas season at the LCBO on Dupont at Huron. These were the days where patrons filled out a coupon and we runners fetched their order in the back of the store. This gave us lots of time to chat about sports, music, politics and wine. If there’s anyone who was more of a cultural clutter box than me it was Rob.

He told me he was working at the Victoria College coffeehouse Wymilwood, doing gopher work for The Bernies— Fiedler & Finkelstein— who owned True North Records and managed the iconic Riverboat in Yorkville. They also managed, among others, Bruce Cockburn and Murray McLauchlan. It all seemed like exciting stuff.

Xmas ended, and we went separate ways. When we next ran into each other I was at the U of T Student Housing service looking for a place for me and my girlfriend at the time. As I pursued the board I saw this guy posting an opening for a place on Albany Avenue. It was Rob. In no time flat I was installed as the third occupant of Mr. Rosen’s walkup rental. It became pizza boxes, newspapers and rotating Dowbiggin roommates for several years.

By this point Rob was getting more and more work from the Bernies. And more releases from the record companies. One day I remember him dashing into the living room, insisting I listen to this hot new record. It was “You Make Me Want To Be” by Dan Hill, who’d been a waiter at The Riverboat. As ever, Rob’s enthusiasm was infectious, and he played the 45 over and over. Another night in 1977 it was Fleetwood Mac’s game-changing Rumors, as we were awed by the new clean, crisp California production sound it represented.

When living in the Albany walkup got to be old, Rob and I took off to his grandmother’s now-vacant bungalow across from Taylor Creek Park in East York. My girlfriend was gone, but Rob was now installed with Lesley, his longstanding girlfriend at the time, and my two cats in our Three’s Company takeoff. For some strange reason he objected to the half-eaten rabbits, birds, snakes and critters my cats brought in each morning.

Having moved from the downtown Rob bought himself a used Renault to get around town. Typically he did zero maintenance on the car as he travelled on tour. One day I heard noises coming from under the hood. I propped it open. Squirrels had moved in. Another time an open basement window allowed a skunk to vaporize our basement for two weeks. It was pure bachelor stuff.

We were also political junkies. I recall us watching the provincial Liberal convention that elected unknown Stuart Smith as (star-crossed) leader in 1976. We saw Smith’s election as transformative. We were wrong. A born and bred Ontarian— Rob never lived outside the GTA— he liked to colour inside the political lines. I was more inclined to contrarian views— which became more pronounced as I settled into Alberta.  His political bent made him conversant with the young student politicians at U of T Student Council (SAC). Rob was a mentor and a friend who gave them a touch of the big time.

I finished my degree, edited the student paper at what was then Erindale U of T campus, and had a play produced at Tarragon Theatre’s writer’s workshop. Then I headed off to travel around the world in 1976-77. Rob, meanwhile was getting more independence from The Bernies. He’d worked a deal with SAC to promote shows at Convocation Hall. I’ll never forget his fledgling show with the late Steve Goodman. We were so excited for him. After the show we were invited to Gordon Lightfoot’s place where I ended up at Gordon’s dining room table examining blueprints for his new yacht with him. It was great to be young and alive, and Rob was bringing us along for the ride.

The unique thing about Rob was his eclectic taste. He loved the music as much as the action of betting on which acts would sell. While CPI did the megastar arena shows at Maple Leaf Gardens, Rob stuck to more intimate venues like Con Hall and Massey Hall. His roster of acts was so diverse. John Prine, Pat Metheny, Tom Waits, Lyle Lovett, J.J. Cale, John Hiatt, Ry Cooder, Maria Muldaur, the McGarrigles, Leon Redbone, Levon Helm, Steeleye Span, George Thorogood, Peter Tosh, Jesse Cook, the Gypsy Kings and so many more were on the bill. Fans knew it was more than a payday when Rob presented. It was always a musical event of acts Rob wanted the public to know.

His onstage intros for the acts— the bearded guy in the beret— and his chiding customers about smoking in the bathrooms were vintage Rob. (Once he let me introduce Jay Leno who rode his motorcycle onto the stage!) So was the affection from the young people at SAC who worked with Rob and got the frisson of showbiz in addition to running student government. (I know this sad news will touch a community of SAC hacks who still revere him.)

In 1983 he stood up as best man at my wedding in the backyard of my parents’ home in Burlington. He was the sound recorder, but 30 seconds in the technical demons switched everything off, committing the ceremony to the “oral tradition”. We thought it might convince him to tie the knot himself, but he somehow managed to avoid matrimony till Mary got him to do the deed last year. I guess we shouldn’t have been surprised as Mary also got him to ski in his 60s.

Eventually he rose the ladder of concert promoters in the country, taking tours across North America with the superstars. For a time he promoted the big summer shows at Molson Amphitheatre. In the winter, it was the O’Keefe Centre/ whatever-its-name-is-now. He’d bring you backstage to meet Robin Williams, Paul Simon, James Taylor, Mick Jagger, KD Lang, Stephen Page, Lucinda Williams. One Sunday night he called me up late to join him for dinner with a guest— who he couldn’t identify. I protested it was too late, and I was tired after doing two shows a day for CBC Toronto. I passed. Missing dinner with Bruce Springsteen.

After years of rubbing shoulders backstage with the stars Rob’s real joy seemed to come from the fine wines he brought backstage after the concert. Many a night as fans and hangers-on mobbed the act, Rob and I sipped a Mollydooker or a Lewis Cab in the corner of the dressing rooms. We were always comparing notes on our latest purchases. Me with U.S. futures, Rob with the latest LCBO treasures. In his spare time Rob began hosting dinner parties at home in Orangeville where he would lead tastings while his beloved partner Mary produced the food.

We also shared a passion for golf. I joined Weston G&CC while he became a ClubLink member at Grandview near his second home, the cottage on Bigwin Island. Despite his short stature, Rob could smash his driver through the many rocky outcrops  at Grandview. He also became legendary among the members at the club for his explosive laugh that reverberated around the entire course.

They nicknamed him The Pirate for his booming Robert Newton laugh and even created an annual tournament in honour of his signature braying. Players wore eye patches in tribute. We liked to call him the hedgehog after his adventures in the rough during our Florida trips.

After golf we’d retire to the cottage to sip wine and debate politics. Unlike so many people these days, political or cultural differences never interfered with Rob’s friendships. He was the most loyal friend to my family, which designated him the sixth Dowbiggin brother. At my father’s memorial service he brought a vintage Cheateau Beaucastel, because my father and mother had visited the winery. You could tell him anything knowing it would (almost) never be repeated. That’s why the acts respected him. What happened backstage stayed backstage.

In our earlier days it was the girls and women we dated, as he teased me about my first-date playlists of Hall & Oates or Boz Skaggs. After I met Meredith in Montreal, we’d compare golf handicaps. As our careers flourished we’d share our satisfaction over his celebrated sell-out concerts, my Gemini Awards and the compelling people we’d met.

As Meredith and I started our family in 1985 with the arrival of our son Evan, Rob became Uncle Rob to our three kids in a five-year window. Not the most paternal fellow himself, he was a great uncle to the kids. In his Raffi days he was godlike. For Evan, our eldest, the pinnace was a backstage meeting in Calgary with John Prime, who autographed Bruised Orange for him.

We were so pleased how Mary’s children Robin and Will came to accept Rob in their lives. And he (belatedly) adopted a parental streak. He was as proud as anyone when Robin was married beside the Ottawa river in Hudson, Quebec. And he played the annoyed parent whenever Will acted like a teenager. It was precious. Lately he became a doting step-grandfather even as ALS took its hold on him.

One of Rob’s signatures was to arrive just in time for dinner. Since our moving west in 1999, getting together with Rob and Mary was less frequent. He often lamented that we couldn’t drop by each other’s homes on a whim or tee up a weekly golf game at Weston or a ClubLink course. But we made time for winter golf in Florida, where during one round Rob absent-mindedly twice stepped over what he thought were logs on a golf course looking to find some Titleist Pro Vs. The logs turned out to be alligators. He still couldn’t see what the fuss was about.

In spite of the great venues and great acts he staged Rob might have been most at home on Bigwin Island in the rocky cliffside cottage he’d purchased. Riding back and forth to the shore in his pontoon boat he felt himself the quintessential Ontario gentleman as he pointed out Shania Twain’s compound or the home of the GolfTown co-founder or the stately Bigwig resort. For an adopted kid who procrastinated about so much, the cottage was a definitive statement about how far he’d come since Norm and Glenna brought him to their home in Willowdale in 1952.

It’s hard to put value on a friendship, but if I was asked to capture our own bond it would be how it helped us grow as men. I can remember us walking one perfect Florida night near my parents’ winter home and saying in astonishment, “Who ever thought we’d get this far when we met at the LCBO in 1974?”  As we all reflect on his impact, that is how I’ll remember Rob, a vital life force with his big laugh and a corkscrew in hand. And a man we can never replace. Good night, my friend. Take a bow in heaven with John Prine.

“Our revels now are ended. These our actors, As I foretold you, were all spirits and Are melted into air, into thin air:”

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BRUCE DOWBIGGIN Award-winning Author and Broadcaster Bruce Dowbiggin's career is unmatched in Canada for its diversity and breadth of experience . He is currently the editor and publisher of Not The Public Broadcaster website and is also a contributor to SiriusXM Canada Talks. His new book Cap In Hand was released in the fall of 2018. Bruce's career has included successful stints in television, radio and print. A two-time winner of the Gemini Award as Canada's top television sports broadcaster for his work with CBC-TV, Mr. Dowbiggin is also the best-selling author of "Money Players" (finalist for the 2004 National Business Book Award) and two new books-- Ice Storm: The Rise and Fall of the Greatest Vancouver Canucks Team Ever for Greystone Press and Grant Fuhr: Portrait of a Champion for Random House. His ground-breaking investigations into the life and times of Alan Eagleson led to his selection as the winner of the Gemini for Canada's top sportscaster in 1993 and again in 1996. This work earned him the reputation as one of Canada's top investigative journalists in any field. He was a featured columnist for the Calgary Herald (1998-2009) and the Globe & Mail (2009-2013) where his incisive style and wit on sports media and business won him many readers.

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Bruce Dowbiggin

With Carney On Horizon This Is No Time For Poilievre To Soften His Message

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Canada awaits the outcome of Canada/ USA Hockey Armageddon II it’s fair to assess just how much a single hockey game has sharpened the focus on the political line brawl between the the nations. The proxies on skates have revealed a few truths about contemporary Canada.

While the Liberal party has suspended reality so that it can pretty-up Mark Carney, Canada’s media instead fawns over conflicting polls showing a Kamala Harris-like ascension of Carney to contender status. Meanwhile, Donald Trump’s Canadian rhetoric gets more belligerent as his 30-day tariff reprieve runs out. Finally, Canadian businessman Kevin O’Leary has advised Trump to delay the tariff Apocalypse till Canada can get an election done.

The common denominator in all this is Conservative leader Pierre Polievre. Or, at least, the mystery of Pierre Poliievre. There are several Poilievres in circulation. There is the Liberal/ NDP version of a nasty wolverine who savages innocent reporters and talks down his nose to opponents.; Next, there is the sunset media’s version of an untested slogan-reciting automaton.

And finally there is the Paul Ryan nerd clone who thrives on explaining kitchen-table economics to people awash in debt and despairing of ever getting ahead in DEI land. Which is the real deal? And does Poilievre himself know who he is anymore?

This distinction is important because, barring a charisma implant for Mark Carney, Poilievre will be the next prime minister, likely with a healthy majority. Neither of the first two Poilievre constructs will disappear soon, of course. The comms teams on the Left are determined to ride over Poilievre, however bad the polls. You need only look at the how the vanquished Left in the U.S. still acts as if they, not Trump, won a mandate last November to understand that Liberals are loath to accept any public rebuke.

The best place to answer the question of who is PP does not come from his apple-eating defenestration of the hapless reporter in B.C. While the MAGA right worshipped that moment and other slap-downs of the press— and the Left demonized him for it— it seems that the Poliievre being groomed by his advisors is meant to be softer and more statesmanlike.

His Saturday rally in Ottawa, shortly before the Canada/ USA hockey brawl, was a good place to start. In the face of Trump’s imminent tariff threat gone was the pitiless street fighter and in came the statesman, full of talk about the glories of Canada and why America needs us.

He seemed intent on tying up the Boomer vote with this speech. Oh wait. Boomers still love Liberals and Carney. Why is Poilievre going after that unwinnable demographic? Isn’t that the quicksand every Conservative, save Steven Harper, has floundered in? But there was Poilievre wandering into Liberal Speak, trying to list the benefits of the nation’s past.

Real Canadians– eg those not voting for Carney– know what a great place it can be. They don’t need to be given a Tourism Canada commercial. And as we wrote last week younger Canadians need a reason to reject Trump’s offer of citizenship. Poilievre needed to level with Canadians about what happened the past decade on defence, crime, DEI. He needed to be frank about money laundering, fentanyl production and the penetration of China’s Communists into the fabric of the land.

While his handlers seemingly urged him to go statesman,  Canadians were willing to hear the truth, not another Carney eye glazer. He needed to channel Harry “Give ‘Em Hell” Truman (“I tell my opponents the truth and it feels like hell.” ) He needed to say he’ll be pitiless in his treatment of those (media, PSA) who stand in the way of a bright new day. As so often happens it was CPC playing on Liberals turf instead of staking out their own. Canada already has Doug Ford, they’re saying. We don’t need another mushy Tory.

Poilievre concluded with a Churchill barb about how America will always do the right thing— after they’ve exhausted the other possibilities. It was an unnecessary and provocative one liner from a guy who’s try to establish his bonafides as the capable negotiator for Canada O’Leary is promising he’ll be. Did he and his brain trust think the thin-skinned Trump would simply slough off the jibe?

It is performances like these that leave Canadians wondering if they’re voting for Poilievre or simply voting against Trudeau and the thoroughly corrupt Liberal/ NDP coalition. Wobbly performances like this will lead to vote leakage to Liberals and to Maxime Bernier’s People’s Party of Canada. Bernier has urged a realistic assessment of Canada’s precarious position vis a vis the USA.

Instead of perpetuating the shopworn homilies to 1970s Canada that have expired, Bernier suggests looking at the opportunities of closer economic— not cultural— cooperation with the Americans. Let Liberal/ NDP moan about collaboration. They’re like the three little pigs expecting their houses of straw and twigs will survive the ongoing attacks of China and international money laundering.

Poilievre has to stop pretending that a heavily indebted and structurally crumbling Canada can withstand the next four years of Trump bombast. He must have an intervention with the Canadian public to bring them to the bracing reality they face. Only when they know which side is up, away from Trudeau, will they start to climb out of this mess.

Bruce Dowbiggin @dowbboy is the editor of Not The Public Broadcaster  A two-time winner of the Gemini Award as Canada’s top television sports broadcaster. His new book Deal With It: The Trades That Stunned The NHL And Changed Hockey is now available on Amazon. Inexact Science: The Six Most Compelling Draft Years In NHL History, his previous book with his son Evan, was voted the seventh-best professional hockey book of all time by bookauthority.org. You can see all his books at brucedowbigginbooks.ca.

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Bruce Dowbiggin

Team Canada Hits American Wall. Wall Wins. Now What?

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You wanted a border war? You got a border war. And just like the political conflict this one came down to Canada’s defence. Or lack of same.

After weeks of a phoney war of words between Canada’s abdicated leadership and America’s newly elected Trump administration, the question of Canada’s sovereignty crystallized Saturday on a hockey rink in Montreal. It was a night few will forget. The 3-1 score of Team U.S. over Team Canada being secondary to other outcomes.

Despite public calls for mutual respect, the sustained booing of the American national anthem and the Team Canada invocation by MMA legend Georges St. Pierre was answered by the Tkachuck brothers, Matthew and Brady, with a series of fights in the first nine seconds of the game. Three fights to be exact when former Canuck J.T. Miller squared up with Brandon Hagel. (All three U.S.players have either played on or now play for Canadian NHL teams.)

Premeditated and nasty. To say nothing of the vicious mugging of Canada’s legend Sidney Crosby behind the U.S. net moments later by Charlie McEvoy.

Those who’d expected a solidarity moment pregame to counter booing the anthem had been optimistic. “Kinda think it might be more fitting for the US team to go stand shoulder to shoulder with the Canadians, under the circumstances. That, I’d cheer.,” said Andrew Coyne. Wrong again.

Expecting a guys’ weekend like the concurrent NBA All Star game, the fraternal folks instead got a Pier Six brawl. It was the most stunning beginning to a game most could remember in 50 years. (Not least of all the rabid Canadian fanbase urging patriotism in the home of Quebec separation) Considering this Four Nations event was the NHL’s idea to replace the tame midseason All Star Game where players apologize for bumping into each other during a casual skate, the tumult as referees tried to start the game was shocking.

But in unprecedented times who could have predicted the outcome? Under-siege Canadians were represented by fans wearing flashing red lights. They’d been urged on by yahoos in the Canadian media to boo everything American they saw, unaware but uncaring if it ruled out Americans playing in a Canadian city when they get the chance.

“It’s also more political than the (1972) Summit Series was,” bawled Toronto Star columnist Bruce Arthur, “because Canada’s existence wasn’t on the line then, and it may be now. You’re damn right Canadians should boo the anthem.”

He got what he asked for. It was as if large segments of Canada had suddenly awoken to their fate in the weeks since incoming POTUS Donald Trump’s tariff threats forced PM Justin Trudeau to resign and prorogue Parliament so his Liberals could stage a succession plan. Or maybe, according to Liberal house leader Karin Gould, postpone the election.

Instead of looking inward to examine what Canada had done to invite trouble the target was instead on Trump, who many believe is supposed to act like a beneficent older brother to Canada. Indignant Canadians are suddenly cancelling winter vacations to the U.S. while boycotting American chain stores like Home Depot and Costco. Even though Canada’s military is a token force following years of Trudeau downsizing and DEI incursions, the sunset media invokes Vimy Ridge and D-Day in their disgust with Trump, who wants Canada (and NATO allies) to actually pay for their defence.

Earlier in the day, presumptive PM Pierre Poilievre echoed the Liberal line with a rally for Canadian unity that would have worked in 1995, not 2025. In a move he may regret he quoted Churchill’s barb that Americans will always do the right thing after every other option has been exhausted. It drew cheap laughs. With luck, Trump’s animus to Trudeau will overshadow this potshot in a critical moment. Or maybe not.

The TV commercials from Canada’s corporate side waved the patriot flag, too. Leading one to wonder had they really missed the Trudeau decade that prompted this? Did they not hear him talking about Canada having no culture now? How it was now postmodern? How it was now 40 million narratives? How he’d lowered the flag for six months in penance for racism and genocide? Apparently not, as they revived narratives from the 1980 Quebec referendum to stir the crowd.

Now, with the symbolic game lost, what’s next? For Team Canada, injured and humbled, there’s an afternoon tilt Monday in Boston against Finland. Only by beating the Finns can they get a revenge game against the American, this time before a hostile Boston crowd. Should they get there would it be Hudson Bay rules again? How will Americans respond? The mind boggles.

Had there not been such a dramatic political overtone, the attention of the media might have dwelt on the fact that this was the first Canada/ U.S. best-on-best contest in 12 years. Excluding the fights it was a monumental display of skill, stamina and, sadly for Canada, goaltending. Why the wait? NHL commissioner Gary Bettman always puts the league’s interests ahead of those who want to see the best players against each other. So expansion and outdoor games took precedence.

Ordinarily the smashing success of the tournament would shame the NHL into more such competitions. And indeed they are conceding to a schedule of Olympics (Italy in 2026) and World Cups in the next decade. As thrilling as any of those contests might be they will likely pale next to Saturday’s drama. In fact, only Game Eight of the 1972 Summit Series can match the explosive political and sports combination of Feb. 16, 2025.

Guesses are now being accepted over just what Canada and Canada’s hockey team’s program might look like by the end of the 2020’s. Once certainty— if the game Saturday is any indication fraternal friendship between the U.S. and Canada will be on hold for a while.

Bruce Dowbiggin @dowbboy is the editor of Not The Public Broadcaster  A two-time winner of the Gemini Award as Canada’s top television sports broadcaster. His new book Deal With It: The Trades That Stunned The NHL And Changed Hockey is now available on Amazon. Inexact Science: The Six Most Compelling Draft Years In NHL History, his previous book with his son Evan, was voted the seventh-best professional hockey book of all time by bookauthority.org. You can see all his books at brucedowbigginbooks.ca.

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