Pittsburgh’s City Theatre is in uncharted territory with new leadership model

By Sharon Eberson

For the first time in the City Theatre’s 46-year history, choices will be made by not one artistic director, but by three. The South Side company announced a new leadership structure last week, with Clare Drobot and Monteze Freeland joining Marc Masterson as co-artistic directors.

Marc Masterson, left, will share City Theatre artistic director duties with Clare Drobot and Monteze Freeland.

Credit: City Theatre 

It isn’t just a sign of the changing times — leadership roles are changing hands, it’s true, but not so much a three-for-one swap. In July, for example, Steppenwolf Theatre in Chicago named its first artistic-director duo. The Wilma in Philadelphia, starting in February 2020, announced a cohort of artistic directors, taking turns as artistic directors over the course of several seasons.

But three at the top puts City in mostly uncharted theatrical waters.

Theatres throughout the United States have been taking action from the top down since being put on notice in July of last year, when We See You White American Theater and Black Theatre United formed soon after the murder of George Floyd. The groups demanded a world in which work environments would “care for and sustain” the artistry and lives of Black, Indigenous, and People of Color.

And they have kept watch. In February, the We See You group released a progress report, in which it said more than 100 organizations had responded with action, and included City’s commitment to “Equity, Diversity, Inclusion and Accessibility,”

The South Side company’s decision to split the artistic role three ways, and the diversity the trio represents, is in line with the creation of the company’s recently released anti-racism plan, in response to the We See You demands.

“I think the field is changing, the country is changing, and I think it’s time for us to let go of some of the legacies of the past and build a way of working that is more collaborative and inclusive,” said Masterson, in his second stint as artistic director of City Theatre.
This is his first time sharing the role, one he also held at Actors Theatre of Louisville and South Coast Repertory in Costa Mesa, Calif.

“I feel like the day of the visionary artistic director who goes up to the mountaintop solo and gets inspired and comes back down and starts issuing orders — that’s the world I grew up in — but I think that day is over or at least changing. And we wanted to be at the front end of this.”
The decision came out of a months-long process, with a key factor the formation of a Succession Planning Taskforce

“We made commitments toward being an anti-racist organization, and part of ‘We See You [White American Theatre]’ was to start a succession planning group, which we did with the board, and in those discussions, the idea began to emerge to try something a little bit different.”

City Theatre’s board of directors unanimously approved the recommendation of the Taskforce to establish a shared structure, for an initial three-year period.

They chose two people who were part of the City family and already acting in leadership roles to join Masterson and form the triumvirate. Managing director James McNeel also is a key player in the collaborative process.
This isn’t the first shakeup at City Theatre in recent years, along with the long shutdown caused by the COVID-19 pandemic.

After artistic director Tracy Brigden’s abrupt departure in 2017, the trio of Drobot, the director of new play development, associate producer Reginald Douglas and McNeel ran the show until Masterson returned as artistic director. He had previously led City Theatre for 20 years, before leaving in 2000. Douglas has since departed for the associate AD’s job at Studio Theatre in Washington, D.C., and Freeland came aboard in that position last year.

The transition after Brigden’s exit “was really formative,” Drobot said. “The idea of leading through consensus and collaboration, which is at the heart of theatre-making … I think that year helped cement some of that. And added responsibility always brings growth with it.”

Nothing formal has been decided about how the newly formed trio will coexist as artistic directors when it becomes official Sept. 6. Their collaboration, however, has been ongoing.

An example is “The Rivers Don’t Know” (a free program, opening Sept. 9 at the Pittsburgh Playhouse), which was inspired by three stories of immigrants and refugees in Pittsburgh: a 1940s steel-mill worker, a Somali family and a class for students with English as a second language. Partners include the Cornerstone Theater Company of Los Angeles and the refugee support group ARYSE.

The project began with a conversation about a community project between Masterson and Drobot nearly two years ago, when he said he wanted to do something about immigrants, and “she ran down the field with it.” When Freeland came onboard, he established a public artisan marketplace for each performance, which will include food and a music set while representing various immigrant groups.

“One of the exciting things in the way this has evolved is that part of it is building a new model and being able to share it,” Drobot said of working as a team. ”It’s something we hope other theatres can learn from as we learn and are able to build it with our colleagues and staff. I think that’s something we’ve been looking at as a whole — organizational culture — and I think all of those things are being called into question right now in American theatre.”

Part of the challenge, she said, is “keeping what is good” in the relationships among artists, audiences and staff, and re-evaluating what can work better.

Freeland has appeared as a performer in companies throughout Pittsburgh, including memorably at City Theatre. He also is a playwright and his theatre experience includes working as an associate artistic director at Pittsburgh Playwrights Theatre Company.

In many ways, he has been preparing for a leadership role since graduating from Point Park University’s Conservatory of Performing Arts in 2009.

“Preparing for it? Yes. But I’m still shocked by it,” he said. “Of course my work at Playwrights and working with Mark Southers was preparation. Mark was so gracious to open up the theatre for me to learn, and that has been a tremendous training ground of how to assert yourself, how to listen, how to make a space for another artist and also to learn the business.”

He also learned about collaboration growing up in Baltimore’s performing arts community, where he no one person every took credit. “It was always, ‘We did it’; it was always ‘Us.’ “ That spirit has continued at City Theatre, he said.

Freeland now finds himself in a position to offer opportunities to underserved or too-often overlooked theatre-makers.

“It’s extremely meaningful to be able to make that happen; to continue to create those spaces where people can feel that sense of freedom, and be free of inhibitions that we didn’t even know were there in some cases,” Freeland said.

The suddenly very public charges of systemic racism in American theatre “hit me pretty emotionally and pretty personally,” Freeland said. “The topics were topics I have been sounding the alarm on for a while. It felt like those were topics we had talked about behind closed doors, and so it was exciting and thrilling and scary at times for those conversations to now be happening in the world. … Getting to City at the beginning of that was great because I was able to learn about the work City had put in place, and I could say, ‘Great. That’s awesome. I can jump on the train.’ ”

Masterson, referring to himself as “the old man here” during a Zoom call with his co-ADs, pointed out that City Theatre can boast a track record of diverse programming and artists and community outreach. He noted that the American theatre reckoning of last year “sharpened our awareness and deepened our resolve, and personally made me understand that I have a long way to go, and we all have a long way to go.”
Masterson added, “So I say that, with awareness and humility, that whatever happened in the past wasn’t good enough.”

He credited Drobot and Freeland with months of work toward the goal of being an anti-racist organization, while acknowledging, “It’s one of those things that’s never finished. As soon as you get to a certain point, there’s more to do. That’s how I look at it.”

One way the company has striven toward inclusivity is the City Connects program. The company seeks out like-minded organizations and invites them through those big red doors on Bingham Street as partners and audience members.

Masterson credits Drobot’s persistence as “the reason why we’re still here.”

“I’ve had a lot of other jobs since I left Pittsburgh,” he said, “and the work that Clare has been doing on community engagement by herself, in addition to all the other responsibilities she has, is much more substantial, much deeper, more honest, than the work I experienced in two organizations quite a bit larger, with staffs quite a bit bigger.”

Drobot’s role in dramaturgy, meanwhile, also puts her in a position as “a gatekeeper” for access and opportunities for playwrights, but also affording a unique perspective on personal and organizational journeys within City’s walls — which brought her back to her role as one-third of of City Theatre’s new artistic director threesome.

“The three people involved in making leadership decisions come from very different backgrounds, but it’s also incumbent upon us to make sure it doesn’t stop there,” she said.

Her broad approach includes support for artists, as seen in City Theatre’s Drive-In Arts Festival of last summer and Spotlight series in which local actors created and performed their own works.

Actors were on their minds, as the trio had taken time out to answer questions on Friday, while auditions were ongoing for City’s Young Playwrights Festival in the fall.

Freeland wanted to take a breather from talking about his role to “shout out the Pittsburgh acting community, who have over this pandemic really showed up and been innovative, acting inside their hallways and closets, and who offer us hope that their spirit has no lasting damage from this pandemic,” he said.

Providing resources and support for performers to get back their in-person mojo and return to some sense of normalcy, “I think that’s what’s going to drive us through this season,” Freeland said.
Some things may never be the same — that “co-” in front of “artistic director,” for example — but for right now, welcoming audiences back for the first time since March of 2020, when COVID-19 put theatre on hold, is a collaboration that everyone can reach a consensus on.

The rest will take some time to evolve, and it may be that as this new world order settles in, other companies will be watching the trio leading a regional theatre company in Pittsburgh.

“Information is and has been shared freely, and I think that has built trust,” said Masterson of sharing a role he has held on his own for four decades. “We work hard at communicating well with each other, and I also feel like we complement each other well, and are each aware of our various strengths and weaknesses.

“I think in some ways, internally, it should feel like a radical shift. It’s one thing to be told what’s happening as you’re leading up to a decision, it’s another thing when you are really plugged in and bear responsibility for choices that are made. So there’s stuff we will have to continue to evolve, and I believe we will.”

Sharon Eberson is a theater critic and the former Arts & Entertainment editor of the Pittsburgh Post-Gazette.

Categories: Arts and Ideas

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