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

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:”
Bruce Dowbiggin
The Game That Let Canadians Forgive The Liberals — Again

With the Americans winning the first game 3-1, a sense of panic crept over Canada as it headed to Game 2 in Boston. Losing a political battle with Trump was bad enough, but losing hockey bragging rights heading into a federal election was catastrophic for the Family Compact.
“It’s also more political than the (1972) Summit Series was, because Canada’s existence wasn’t on the line then, and it may be now. You’re damn right Canadians should boo the (U.S.) anthem.” Toronto Star columnist Bruce Arthur before Gm. 1 of USA/ Canada in The 4 Nations Cup.
The year 2025 is barely half over on Canada Day. There is much to go before we start assembling Best Of Lists for the year. But as Palestinian flags duel with the Maple Leaf for prominence on the 158th anniversary of Canada’s becoming a sovereign country it’s a fair guess that we will settle on Febuary 21 as the pivotal date of the year— and Canada’s destiny as well.
That was the date of Game 2 in the U.S./Canada rivalry at the Four Nations Tournament. Ostensibly created by the NHL to replace the moribund All Star format, the showdown of hockey nations in Boston became much more. Jolted by non-sports factors it became a pivotal moment in modern Canadian history.
Set against U.S. president Donald Trump’s bellicose talk of Canada as a U.S. state and the Mike Myers/ Mark Carney Elbows Up ad campaign, the gold-medal game evoked, for those of a certain age, memories of the famous 1972 Summit Series between Canada and the USSR. And somehow produced an unprecedented political reversal in Canadian elections.
As we wrote on Feb. 16 after Gm. 1 in Montreal, the Four Nations had been meant to be something far less incendiary. “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.
“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.”
With the Americans winning the game 3-1 on Feb. 15, a sense of panic crept over Canada as it headed to Game 2 in Boston. Losing a political battle with Trump was bad enough, but losing hockey bragging rights heading into a federal election was catastrophic for the Family Compact. As we wrote in the aftermath, a slaughter was avoided.

“In the rematch for a title created just weeks before by the NHL the boys stuck to hockey. Anthem booing was restrained. Outside of an ill-advised appearance by Wayne Gretzky— now loathed for his Trump support— the emphasis was on skill. Playing largely without injured Matthew and Brady Tkachuk and McAvoy, the U.S. forced the game to OT where beleaguered goalie Craig Binnington held Canada in the game until Connor McDavid scored the game winner. “
The stunning turnaround in the series produced a similar turnaround in the Canadian federal election. Galvanized by Trump’s 51st State disrespect and exhilarated by the hockey team’s comeback, voters switched their votes in huge numbers to Carney, ignoring the abysmal record of the Liberals and their pathetic polling. From Pierre Poilievre having a 20-point lead in polls, hockey-besotted Canada flipped to award Carney a near-majority in the April 28 election.
The result stunned the Canadian political class and international critics who questioned how a single sporting event could have miraculously rescued the Liberals from themselves in such a short time.

While Canada soared because of the four Nations, a Canadian icon crashed to earth. “Perhaps the most public outcome was the now-demonization of Gretzky in Canada. Just as they had with Bobby Orr, another Canadian superstar living in America, Canadians wiped their hands of No. 99 over politics. Despite appeals from Orr, Don Cherry and others, the chance to make Gretzky a Trump proxy was too tempting.
We have been in several arguments on the subject among friends: Does Gretzky owe Canada something after carrying its hockey burden for so long? Could he have worn a Team Canada jersey? Shouldn’t he have made a statement that he backs Canada in its showdown with Trump? For now 99 is 0 in his homeland.”
Even now, months later, the events of late February have an air of disbelief around them, a shift so dramatic and so impactful on the nation that many still shake their heads. Sure, hockey wasn’t the device that blew up Canada’s politics. But it was the fuse that created a crater in the country.
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 . His 2004 book Money Players was voted sixth best on the same list, and is available via brucedowbigginbooks.ca.
Bruce Dowbiggin
Don & Rick: Canadian Icons, Mixed Messages, Lasting Impacts

“Well, Tim, this is our last show. . . . Thanks everybody for listening and toodaloo,” 91-year old Don Cherry allegedly on his final podcast episode.
Once upon a time in a public broadcaster far, far away there was an identity crisis. Who should we be as we enter the 21st century? We depend on government for our financing, but our audience relies on people who hate government.
At CBC that argument could be summed up by two figures on the TV network. Rick Mercer. Don Cherry. Both were brilliant communicators, masters of the craft of holding eyeballs. But they represented diametrically opposed audiences. Mercer was the glib political voice of This Hour Has 22 Minutes. Cherry was the bombastic voice of Hockey Night in Canada, as Canadian as the brown beer stubby.
Mercer was worshipped by the folks in the C suite and liberal media. With his searing walking shots he lanced egos and asked uncomfortable questions. He called out sacred cows. Yet there was never any doubt in CBC’s upper reaches about whose side he was on in the culture war at CBC. He was safe.
Cherry was the unpredictable occupant of Coach’s Corner, the bombastic voice of white anglo hockey culture. He was abrasive and unforgiving. His first-period rants beside his Topo Gigio Ron Maclean were must-watch for the demographic. They also, it seemed, constituted must watching for his critics.
[Confession: I was one of his critics, paid to be so. We tangled often over his act. He ripped me in the 2004 NHL playoffs, alleging I said he was insincere about kids with cancer. During the infamous 1987 World Junior brawl he said I was a coward who wouldn’t defend his own kids in a fight. etc. He sicced his bots on me. While I disagreed with much of what he said, I defended his right to say such things. My beef was mostly with HNIC which refused to allow any dissent to Cherry’s act on the show . It was a noisy one-note symphony.

Don was durable, holding his prime position for decades, putting himself above the title many Saturdays with headline material. In the sea of pearl clutchers at CBC he stood out. While the suits above recoiled at his Canadian Legion catechism, they also knew he was an asset they could play when they went for funding in Ottawa. “See, we have all sorts of political views on the network.”
When CBC lost its HNIC franchise to Sportsnet Cherry became someone else’s problem. Eventually the Woke folk at Rogers tired of telling him to knock off the politics and cultural stuff. He was let go in 2019 for saying what he’d always said. Maclean then put in the knife to save his own hide.
Mercer’s highly rated act continued unabated till 2018. One of his most popular gigs— the one most likely to appeal to posh Canadians— was talking to Americans about Canada. It was brilliant in its simplicity. Go to famous colleges and universities to plumb the depths of their Canadian knowledge. Likewise, buttonhole well-known American politicians.

The topics were many and ridiculous. Should Canada protect the famous location Joe Clark’s Hole? What should Canada do about its melting national igloo? Could they congratulate Jean Chretien on a rare political feat called a “Double Double” in which he received support from both sides of the Canadian parliament.
He asked Al Gore about Canada moving the capital city from Kingston, Ontario to Toronto (Gore thought it smart). He convinced tourists at Mount Rushmore that the mineral rights to the mountain had been sold to a Canadian firm that was getting ready to drill for oil in Lincoln’s forehead.
He asked Americans to condemn Canada’s practice of euthanizing senior citizens by setting them adrift on Northern ice floes. In a famous moment, future President George W. Bush failed to correct Mercer when he referred to Chrétien as “Jean Poutine”
Mercer always said he didn’t think Americans were ignorant. Eighty percent had the right responses and those never made it to air. For the rest it was just that they couldn’t resist an open mike and having a take on things they knew nothing about. He had affection for them.
For Canada’s Left, insecure in its northern faculty-lounge, that subtlety was lost. Mercer’s routines reinforced a smug anti-American attitude in the Liberals and NDP base. All they saw was a nation of nitwits. “Look, what bozos!” The orientation of the fashionistas turned away from the U.S. to supposed European sophistication and societal controls for climate, population growth and Covid. Hello, Mark Carney.
This bias was reinforced by the increasingly self-loathing voices on the cable news of the American Left. Every GOP figure from George W. Bush till Trump today became a comic character. Canadian lefties adored it. As we’ve written often the snide attitude allowed Canadians to ignore that Americans were protecting them for free and keeping them rich. And taking the overflow from Canadian’s prized healthcare system.
This arrogance culminated in the March election where the mere mention of Trump sent Canadians fleeing back to a Liberal administration that was moribund after a decade of incompetence. It has an echo in Toronto’s Hockey Hall of Fame again declining to award Cherry the Foster Hewitt award as a legendary TV journalist. Love him or hate him he’s earned it. It’s arguable whether the aging Cherry will even be around to be chosen next year.
For sure his political impact will resonate for long after he’s gone in the populist resurgence in western Canada and elsewhere. If only Rick Mercer were allowed back on CBC to cover it.
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 . His 2004 book Money Players was voted sixth best on the same list, and is available via brucedowbigginbooks.ca.
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