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Andrew Alexander sits onstage at The Second City in Chicago on Nov. 18, 2009.

Charles Rex Arbogast/The Associated Press

Knowing when to step down and move on in the arts is an art itself – and if you want a clear illustration of the perils of staying in a position of power just a couple of years too long, look no further than Andrew Alexander.

Two summers ago, the Brampton, Ont.–raised comedy, film and television producer was surrounded by loved ones at Rideau Hall as he received a lifetime artistic achievement award from the Governor–General. He was honoured for his work as CEO and executive producer of The Second City comedy theatres in Toronto, Chicago and Los Angeles and, of course, for producing its legendary TV spin-off SCTV, starring John Candy, Eugene Levy, Andrea Martin and Catherine O’Hara.

Flash forward to this summer, however, and Alexander, 76, has stepped down from overseeing Second City’s operations in the wake of charges of institutionalized racism aimed at the great comedy institution, charges that Alexander did not refute in a rueful resignation letter.

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“The Second City cannot begin to call itself anti–racist,” he wrote on June 5, promising to divest himself of his 46-per-cent stake in the private company. “This is one of the great failures of my life.”

Since then, Second City has been subject to multiple open letters from Black, Latinx and queer alumni – calling for investigations into everything from microaggressions and tokenism, to verbal abuse and sexual misconduct.

“We are prepared to tear it all down and begin again,” Second City’s president and managing partner Steve Johnston and chairman D’Arcy Stuart wrote in response, pledging that an independent human resources firm will look into all the allegations.

So what is Alexander’s life legacy in the end – building Second City up into one of the world’s top comedy brands, with revenue reaching almost $80–million, or leaving it in a tear–down state?

The improv impresario sounded torn in a phone interview with The Globe and Mail from Los Angeles, where he is now based. In fact, he was even torn about giving an interview – sending a short statement first, then changing his mind the next day and deciding to talk.

“It is hard – it wasn’t what I anticipated, as I was gonna exit the company at some point,” he says. “But I hope my legacy will be that, you know, it will move into a new phase – and the new generation will really respond.”

At times, Alexander – who saved the Toronto franchise in 1973, then took full ownership of Second City with his late business partner Len Stuart in 1985 – was eager to mention comedy diversity initiatives he championed, dating back to L.A. riots in 1992. At others, he wanted to make clear that he isn’t dodging responsibility and that he didn’t do enough in evolving his soon–to–be former company from its white roots.

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But while Alexander has taken the fall for widespread problems at Second City, he also believes that the comedy company might have been able to avert this crisis if he had been more hands-on and picked up on “issues” that built up into a “powder keg.” “If I have one big regret, it is that over the last nine years, I was spending not nearly enough time either in Toronto or in Chicago,” he says.

What ignited Second City’s powder keg was, like so many similar reckonings over institutional racism currently taking place at cultural organizations from theatre companies to museums, a spark of hypocrisy in the wake of the killing of George Floyd by police in May.

In this case, the official @TheSecondCity Twitter account sent out a Black Lives Matters message that added: “To say nothing is to be complicit.”

On June 4, the Black comedian Dewayne Perkins, a writer on Brooklyn Nine-Nine and Second City Chicago alumnus, took up the implied challenge – using that corporate tweet to kick off a Twitter thread listing alleged racist incidents. from white directors saying the n–word, to Black actors being sent to speech therapy to appeal to white audiences.

It was not exactly a secret that there were race-related problems at Second City, however, and especially in the United States since Donald Trump’s rise to president in 2016.

In his farewell apology, Alexander made reference to a Chicago sketch show from that year called A Red Line Runs Through It – which saw an exodus of performers of colour due to heckling that veered into hate speech.

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“Trumpers, you know, made their way into the audience and were pretty emboldened, particularly when there were interactive parts of the show,” Alexander says. “We brought in security – the first time in history we’ve ever had to do anything like that. … But I think that the actors felt that was not enough.”

Toronto hasn’t had a similar headline-making flash point. But Second City’s current bi-national leadership, in a group Zoom interview, is eager to make clear they are working on systemic issues across the company. A listening session has been held with the Canadian talent, staff and alumni in which grievances were aired – and an independent HR firm will investigate any allegations received via hotline set-up stemming from this side of the border too.

“Chicago, L.A., Toronto are all part of the same company and same family,” says Anthony LeBlanc, now interim executive producer as the company searches for a permanent replacement who, it has promised, will be BIPOC (Black, Indigenous or a Person of Colour). “So the changes that we’re doing, it applies to everywhere.”

Johnston, based in Chicago but originally from Oakville, Ont., says the company is going to “get inside of all of the systems and the processes and everything that has been part of our way of doing things for 60 years in Chicago and coming up to 50 in Toronto.”

“DEI [diversity, equity and inclusion] should be the center of everything that we’re doing moving forward,” says Parisa Jalili, recently promoted to chief operating officer.

For those comedy fans who go to Second City to laugh at its classic mix of sketch and improv, rather than for its HR practices – and perhaps, equally, for other comedy fans who have gone elsewhere due to a feeling the brand has dated – the area of most interest in these discussions is how the comedy will approach the audience from a DEI perspective.

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Second City Toronto saw around 117,000 attendance in 2019 – but the impression is those spectators were mostly white in a city that is mostly not. “I think the [Toronto] casts have been pretty diverse for the least the last 10 years, but the audience is not as much,” Alexander says. (Internal numbers from Second City say 40 per cent of Toronto casts were BIPOC pre-pandemic.)

This is an underlying challenge, LeBlanc says: “If your audience is mostly a homogeneous group of people, then that starts to determine what is funny, which starts to determine what makes the show, which determines who we hire to be in that show.”

While the messaging has been that Second City is prepared to tear it all down, in Toronto, the organization has been quietly planning changes since last year – aiming to expand its audience(s) as it prepares to expand into a new 28,700–square–foot space that will feature three comedy theatres, classroom space, a “games–driven” bar and restaurant.

To that end, it has been absorbing leadership from the city’s vibrant indie comedy scene on Bloor Street West centred around The Comedy Bar and Bad Dog Theatre.

Gary Rideout Jr. and James Elksnitis – who co–founded Comedy Bar in 2008 – joined Second City as executive producer and vice-president of business operations in early 2020, while Julie Dumais Osborne – who was the artistic director of Bad Dog – has been taking over leadership of the local the Second City Training Centre.

The new theatres are necessary for the Toronto team to fulfil one of Second City’s pledges here – to create shows by and specifically for BIPOC communities.

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Second City Toronto has already been experimenting with secondary offerings in anticipation of the move, Rideout says, pointing to She the People, an all–female sketch show, and its recent partnerships with Extravaganza Eleganza, a “queer–forward” sketch comedy group, and Tita Collective, an all–Filipina troupe. “We know we have to go beyond that,” Rideout says. The additional hope is that audiences invited into the Second City space to see a culturally specific show will then grow comfortable it in, trust it and try other offerings; Rideout has seen that happen at Comedy Bar, where he says there’s a “cross–pollination” of audiences.

Making sure the Second City brand is inclusive is important beyond the box office, in selling its other products: Its training centre’s improv and sketch classes, which have an average enrollment of 11,000 annually, and its various corporate services that count, among their clients, pharmaceutical companies and Silicon Valley giants.

While the pandemic has led to furloughs on the sketch show side, those other aspects of of the business have pivoted fairly successfully online as people and companies yearn for different ways to connect. All of which means that Second City, with revenue still coming in, is in a better position to implement the changes being demanded compared to, say, Chicago’s iO comedy theatre, which recently shut down permanently in response to the twin challenges of COVID-19 and its own charges of racism.

Second City won’t release financial information about how much of its income comes from training and corporate work – but ex-CEO Alexander says it has experienced “rapid growth” this century due to these streams, going from about 40 to many hundreds of employees.

“When it came to diversity, my primary interest was the voice on stage, making sure that our stages were diverse and gender equal,” he says. “As the company grew, I don’t think I personally was paying attention to the rest of company, where you have more employees. We could have invested more in getting more POC on our admin staff and producing staff.”

As that reflexive “we” suggests, it’s clearly going to be hard for Alexander to let go of Second City. “I’m not dead, by the way,” he says, but the personal plans for the future he mentions are Second City adjacent, from getting Martin Scorsese’s SCTV documentary to the finish line, to spearheading more fundraising for the Second City Alumni Fund, which he hopes to broaden to the wider comedy community.

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The producer has hired a investment banker to find an entity to acquire his Second City equity in the company, but wants to make sure it’s the right ownership.

“I want the company to continue to last for another 60 years,” he says. “You know, it’s a living, breathing organism that is sort of reflective of the world we live in.”

“I think what’s going on right now is we’re kind of right in the middle of it, right? It’s all very messy.”

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