Oregon Shakespeare Festival’s new leader on 90th season and securing its financial future

The Oregon Shakespeare Festival in Ashland is celebrating its 90th season. It’s long been one of the most prestigious professional theatres in the nation. But in recent years, it’s faced slings and arrows — from declining audiences and funding to wildfires and the pandemic.

Executive Director Gabriella Calicchio began last fall after more than 25 years leading arts organizations in California and elsewhere. She joins us to talk about what OSF will do to appeal to audiences and regain financial footing — in the short and long term future.

Note: The following transcript was transcribed digitally and validated for accuracy, readability and formatting by an OPB volunteer.

Dave Miller: This is Think Out Loud on OPB. I’m Dave Miller. The Oregon Shakespeare Festival (OSF) in Ashland is celebrating its 90th season this year. It’s long been one of the most prestigious professional theaters in the country. But in recent years, it’s faced a whole series of problems – from declining audiences and funding to wildfires and the pandemic. There’s also been a lot of leadership turnover in recent years. Its new artistic director, Tim Bond, took over about a year-and-a-half ago. Its executive director, Gabriella Calicchio, began last fall. She has spent more than 25 years leading various arts and culture organizations. She joins us now to talk about the future of one of the most prominent theaters in the country. Welcome to Think Out Loud.

Gabriella Calicchio: Thank you, Dave. Glad to be here.

Miller: I’m glad to have you on. When did you go to OSF as an audience member for the first time?

Calicchio: Well, I actually went in 2003 for my honeymoon. We came up here and spent, I think it was three days, saw five shows, stayed in company housing. That was my first introduction to OSF and I was pretty much blown away.

Miller: But embedded in that answer … I think it shows us something about how important theater was to you or maybe even how enmeshed you already were in the theater world if you chose to see five plays for your honeymoon with your spouse. I assume your spouse was up for that?

Calicchio: Well, yes, he was an actor at the time. And it was the best possible honeymoon we could have had, given the fact that we both were so passionate about theater.

Miller: Do you remember what the Oregon Shakespeare Festival meant to you at that time? I mean, how you thought about this particular theater company.

Calicchio: Yes, because I’m from the East Coast. I moved out to California in ’96 and I’d heard about OSF but not a lot. And then when I moved to Marin Theatre Company, so many of our patrons and donors traveled up here at least once a year to see shows at OSF. So that’s how I first started hearing about this magical place because that’s the way people talked about it.

And my husband had grown up coming here and had been here many, many times. So I was prepared to … Well, I don’t actually think I was prepared for the level of excellence and what I walked into, but I was prepared for something that was bigger than anything I’d been exposed to prior.

Miller: What went through your mind, much more recently, when you heard about this job opening?

Calicchio: As it happened, I knew Bill Rauch, and when he took over the job in 2007, he invited me up here to actually talk to him and talk to Paul Nicholson about taking over that position when Paul retired. And thankfully, Paul was very sensible. Paul said to me, “You know, if you really want to do this, you need to go run a much larger theater.” Because at the time, Marin Theatre Company had a $2.5 to $3 million budget and OSF had a $28 million budget.

So I went off to run the Children’s Theater Company in Minneapolis. And after that, we went back to Marin and we decided that that’s where we wanted to raise our children. So every time I got a call about this position here, I said, “No, we can’t move, we’re here.”

It just so happened that the day after my son, who was my youngest, committed to Johns Hopkins for college, I got a call from the recruiter. This time around, I looked at my husband and I said, “Oh my God, we could actually do it now. We could actually do this.” And here I am.

Miller: Although, in that intervening time, the festival that had meant a lot to you – and it seems from the way you’re describing it, it has been this goal, in a sense – it had been through such intense traumatic financial times that there were questions in recent years about how viable OSF’s future is. Can you give us a sense for the challenges that the festival has been facing before you arrived, what you stepped into?

Calicchio: Wow, that’s a big one. So, the challenges that most people say were due to the pandemic actually went farther back for OSF than the pandemic. One of the first things that I did – well, actually a board member did – was put together 11 years of the audited financials starting in 2014 and going through 2024. And what we saw when we looked at the financials was that all but two years during that period had been run at a deficit.

So, although the pandemic kind of put the pin in it, the issues with the financial situation at OSF started long before the pandemic. What the pandemic did was bring so much uncertainty, leadership change, and obviously, almost a full season without programming. What I realized was that the structural deficit that we have been wrangling with here had more to do with the way that we were programming and budgeting than it did with the actual pandemic itself.

Miller: What’s an example of that? So, nine of 11 recent years are in the red and you’re saying that it’s not even initially the pandemic at all – it’s structural. What’s an example of that?

Calicchio: Well, I think the best example of that is that traditionally OSF was able to program the season, announce it, and in some cases even go on sale with it before they had an approved budget for the season. And they were able to do that because in the old days they knew what their numbers were. They knew they were going to be selling at 80% or 90% capacity in all of their venues and they could count on a definite number for revenue. So programming was easy because you just knew that you had to program within that number.

So that’s the way it was. What’s happened in recent years is that, even beginning a decade ago, the ticket sales weren’t as assured as they had been in the past and the cost of producing this kind of theater had grown exponentially. So all of a sudden trying to do those two major components of producing theater separately no longer really worked.

Miller: What you’ve just described there – is that either unique or pretty particular to OSF, the loss of the predictability of theater-going, theater-paying audience? Or is that something that is mirrored at other really high-profile theaters across the country starting, say, in 2014?

Calicchio: I would say that it is mirrored in other pretty high-profile theater companies. And I think it actually probably started with the recession in 2008. And I think that’s when this generation of uncertainty began. The fix to it seems relatively simple, right? You program and you budget simultaneously, and you don’t separate those two processes.

It’s been interesting talking to my colleagues across the country about what their theaters are doing. And I think a lot of theaters did fall into this kind of programming, where boards were either adopting deficit budgets or they were adopting budgets long after the season had been determined. So bringing those two things into alignment, I believe, is the key to the future for OSF, or one of the larger components that we have to address in terms of the future.

We’ve done that by creating a five-year financial plan, which I’ve also just learned is not unique. Many of our colleagues have done that. Some of our colleagues got a head start because we’ve had so much leadership change that we’re only doing this now. But a lot of theaters across the country coming out of the pandemic put together five-year financial and producing plans so that they could work their way out of what has been really, really tough time for the American theater.

Miller: What do ticket sales look like right now?

Calicchio: They’re great! I’m so excited you asked that question. Last year, we sold 172,000 tickets. And this year we are budgeted to sell223,000 and we are absolutely on track to meet our mark. During our pre-sale period, ticket sales were 50% higher than they were last year and we are trending pretty steadily at about 30% higher than ticket sales were last year. So we’re really excited, and more than anything, our audiences are excited.

The shows that we have running right now are all incredible in terms of the quality of the actors, the quality of the direction and production quality. And people are recognizing it and they’re thrilled. The whole tenor has changed. Even in the short period of time that I’ve been here, since the end of last season to the opening of this season, you can feel the difference. It’s a pretty great feeling.

Miller: You were talking earlier about the kind of more invisible-to-an-audience decisions that you have to make, in particular, simultaneous programming and budgeting. That’s an executive director kind of decision, but I’m curious about the connection that you see between programming choices – what plays you’re going to put on – and your bottom line?

Calicchio: That’s a really good question. I work very closely with Tim Bond, the artistic director, and I will be working … Programming our 2027season will be the first season that I’ve really been involved in from the beginning and …

Miller: Because right now, in April of 2025, you’re in the process of thinking about what’s going to be on the main stage in, say, July of 2027?

Calicchio: Correct. As Tim likes to describe it … I’m still learning the rotating rep, because that is a unique model in this country. But as he likes to describe it, we’re in three seasons at all times. We’re in the season that we’re actually producing, we’re thinking about the season that we’ve already committed to and set, and then we are beginning to plan the third season, which in this case is 2027.

In most theaters, there’s a very direct correlation between what you put on your stage and your ticket sales. In the old days, when many theaters had huge subscription bases, that wasn’t so much the case because you had a loyal audience that would come to everything and they would say, “Ah, I liked that one,” or, “Wow, that one really, really moved me.” But they would still come because they bought a subscription, and that way was their way of supporting the art and taking chances.

That has also changed for a lot of the subscription houses across the country, but we have a different model. We have a membership model, not a subscription model. And I believe that once our audience members comeback, they are pretty loyal to OSF and to the season. What’s interesting is that 50% of our audiences are new each year and that does not include our student groups, which, by the way, our student group numbers are coming back in droves.

In 2024, we had 274 student groups that came to this campus to see shows and do workshops. And this year, as of a month ago, we’d already booked 307 groups. So it’s clear to me that as soon as we were able to say, “Tim Bond is here, OSF is back,” the public is responding to that, whether it’s schools or just the general public. And that’s fantastic. I mean, that’s what’s going to help us get through the next five years.

Miller: I know it’s more complicated than this, but on some levels, I think about the kinds of programming decisions that people like Artistic Director Tim Bond, but also you and others involved in the theater in very different ways, have to make on the most stripped down level … how much old stuff, how much Shakespeare or Elizabethan plays you can put on, how much newer stuff that could challenge audiences in different ways, could be more explicitly about contemporary themes, and how much of that do you put in. How do you think about that balance?

Calicchio: Well, the tradition at OSF, at least in the recent decades, has been to do three, maximum four, Shakespeare productions a year. This season, we are doing nine shows and three of them are Shakespeare. So it’s a third of our season. But the Shakespeare that we do, and the way that we doit, typically makes it relevant for people today. I mean, our “Julius Caesar, “we just opened “As You Like It,” and “The Garden of Arden” is set in the ’60s.And it’s just really fun and colorful, but it’s telling the story so clearly that anybody in the audience can follow it and understand it. And I think the challenge that people have with Shakespeare is that oftentimes, they can’t follow the story. I think what OSF does so well is ensure that the story is told and that it’s clear.

The rest of what we do is some classical, but really a lot of contemporary work. Right now, we’re doing “Fat Ham,” which is obviously a Pulitzer Prize-winning play. It’s very contemporary and it’s an incredible production. The houses are beginning to really get full and sellout. “As You Like It” in June is almost completely sold out. But we’re also doing August Wilson’s “Jitney,” an incredible production that Tim Bond direction – and people are loving that.

So, we offer a pretty good mix. And what Tim and I like to say is that it’s “OSF for all.” It doesn’t matter who you are, where you come from, what color your skin is. You step on our campus, you’re stepping on a red carpet. And there is something for everyone. If you want comedy, there’s comedy. If you want a musical, there’s a musical. If you want classical Shakespeare, there’s classical Shakespeare, etc. I mean, that is what OSF needs to be. OSF for all. Everyone is welcome and everyone will find something that they can connect to in our programming.

Miller: When you say that as kind of your unofficial motto now, is implicit in that a sense you’ve gotten from older or long-standing audience members that they didn’t feel like OSF was still for them? I mean, is that a direct response to what you’ve heard?

Calicchio: That’s an interesting question. I’m not sure that I would say that it’s a direct response to what I’ve heard, but I think it is response to what we actually are and what is needed in our community.

Miller: I want to go back to where we started, apropos of your honeymoon at a theater, taking in five shows. Over the course, then, of you executive director career, you definitely spent some time with theaters at different levels. But most recently it was at a broader Marin County arts and culture organization. What does it mean to you to be back at a theater?

Calicchio: Everything. It means everything. I was at the county of Marin for a decade and we did some incredible work there, including founding a nonprofit that now serves as the arts council for Marin. But we also did programming that was really special and dear to my heart, all sorts of different kinds of arts programming and grants for the arts. But I have missed being in a producing theater organization.

I could have stayed at the county for another five years and retired. But when this opportunity came up, I just knew that I had to be here and I had to take it. And I feel like, because I’ve had a massive career, I’m at a point where hopefully I can really be of use here. I can take all of that experience and that confidence in knowing that I’ve turned around not one but two organizations, that it is possible to do this work at this time.

And I love theater. Oh my God. I got to sit in the house for the opening of “As You Like It.” I’ve seen “Fat Ham” twice. I’ve seen “Jitney” twice. I love being in this environment again. And I grew up in it, which I neglected to say. My father was a playwright and a translator of Italian-to-English plays. Obviously, he didn’t make a living by that or you would know his name. He taught for a living. But I grew up in the theater. It’s all I’ve ever known and all I’ve ever wanted.

Miller: Gabriella Calicchio, thanks so much for your time.

Calicchio: Thank you.

Miller: Gabriella Calicchio is the executive director of the Oregon Shakespeare Festival in Ashland.

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