Winnipegger gets Tony nod for Broadway producer role

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This article was published 21/05/2025 (451 days ago), so information in it may no longer be current.

Rafaella (Raffie) Rosenberg has been having a very good year.

The 32-year-old from Winnipeg co-produced her first Broadway show, Oh, Mary!, last summer. In May it was shortlisted for the Pulitzer Prize and picked up five Tony Award nominations; Rosenberg herself is nominated for a Tony in the Best Play category.

“I was sitting with my other two co-producers and, of course, we were very excited but also it’s a bit of a relief because the hype is way too big!” says Rosenberg with a chuckle.

“Everybody’s saying that it’s inevitable, but what if they jinx it?”

Rosenberg is self-effacing but clearly not superstitious. She’s a passionate theatre lover new to Broadway producing, but she talks about fledgling theatre projects like a seasoned strategist eyeing a promising stock — assessing risks and scanning for signals others might miss.

A 2022 grad from Columbia’s master of fine arts program in theatre management and producing, Rosenberg saw an Off-Broadway production of Oh, Mary! for the first time last year.

“I had no context, and I’m like, wow, that was amazing. It’s the silliest, dumbest, funniest thing I’ve seen in a long time.”

Rosenberg isn’t alone in embracing these descriptors.

Oh, Mary! is “the stupidest play,” Cole Escola, its author and current star (as Mary), remarked last summer.

“I have a huge hunger for deep stupidity,” Sam Pinkleton, its director, echoed.

In the play’s warped vision of 1860s Washington, Abraham Lincoln is gay, while his wife and beard Mary Todd Lincoln is a washed-up drunk obsessed with reinventing herself as a cabaret star.

The show is set in the fourth year of the Civil War — “the South of what?” Mary keeps asking — and in the final days before Lincoln’s assassination, the play’s inevitable climax.

Sold-out shows and gushing reviews suggest they’d stuck the landing even before the award nominations flooded in. But not everyone believed in the play’s mainstage and mainstream success.

“There were people who thought it shouldn’t go to Broadway, including people that I trusted. To me, it seemed like it was a no-brainer,” Rosenberg says.

“But it doesn’t mean that I was right and they were wrong. It just means that my perception of it was different. In hindsight, it seems inevitable, but at the time, it’s always a gamble.”

A Broadway co-producer is part fundraiser, dealmaker and cheerleader. They mobilize investors, help secure precious financing and use their networks to build buzz. Shows flop fast and easily but when things really work, the payoff —financially and for their careers — can be big.

Rosenberg is careful not to exaggerate her role in transforming Escola’s play into the smash hit it is now, but the task in front of her as a first-time Broadway producer was as vital as it was daunting: raising, alongside the other co-producers, US$4.5 million — expenses ultimately recouped within a couple of months after the production’s July 2024 opening.

As a fairly recent New York transplant, she’s had to be especially resourceful, building a network from scratch in a city where many theatre professionals have lifelong industry ties.

While interning at The Late Show With Stephen Colbert, she created lasting relationships with fellow interns who later formed a co-producing unit with her on Oh, Mary!

Working weekdays with Emmy-winning comedian Alex Edelman (his Just for Us special is streaming on Crave) on a whirlwind of projects, she carves out time with her collaborators to discover and develop other comic talents, scouting at fringe festivals, late-night shows and wherever funny people gather.

She also points to earlier experiences in Winnipeg as formative.

“I talk about Winnipeg all the time and love being from Winnipeg. It was a great place to grow up,” says Rosenberg, who studied dance at Shelley Shearer School of Dance and Kickit dance studio in Winnipeg as a youth and attended St. John’s-Ravenscourt School.

“But I am totally fine saying this on the record: (SJR) really did not put an emphasis on arts. Despite valiant efforts by the arts teachers, who really are very passionate and try really hard, they don’t have really any administrative support for it.”

In her 20s, Rosenberg moved to London, Ont., to study at Richard Ivey School Business School at Western University, where she graduated in 2016.

“Learning everything in theory is a lot of fun, but doing it in practice is really different. The plan was always to work in marketing for a couple years and then figure out how to get back into the arts, maybe in a business role, but I did an internship in marketing that I was horrible at,” she says.

A turning point came when she produced a couple of Winnipeg Fringe Theatre Festival shows with Camille Inston in 2017 and 2018. Both were audience and critical favourites; the 2018 show, The Last 48, had a sold-out run.

Now that she’d had a taste for the practice, she craved the theory, leading her to Columbia’s master’s program.

While the U.S. has a robust non-profit theatre scene, it lacks the levels of government arts funding Rosenberg was accustomed to in Canada. Broadway, meanwhile, is comparatively big business and much more commercial — a contrast that shapes her perspective.

“There are pros and cons to both models,” she says.

Rosenberg highlights Broadway’s commonalities with Hollywood, where tens of millions of dollars must be raised to back projects that must sell big or go home. Add to that ticket prices that can soar to US$1,000 or more, and it’s clear: this is high-stakes entertainment, not just art for art’s sake.

And while the non-profit model can mean safeguarding theatre artists to experiment with new ideas, Rosenberg says “at its worst it creates a closed loop of putting on shows that are going to sell just enough tickets to sustain your operating costs.”

This can be a damper on creativity too.

“At their best, both the non-profit and for-profit models work in tandem to grow the art form,” she says.

conrad.sweatman@freepress.mb.ca