Orlando Watson Shakes Up Tri-C JazzFest As Its New Executive Director: Q&A

This year, from June 25-27, audiences will be able to experience the Tri-C JazzFest they know and hold dear, but with a fresh take. At Playhouse Square venues, musicians like Sheila E., Durand Bernarr, the Ohio Players and more will light up the stage with their musicianship and soul. Behind Tri-C JazzFest’s impressive 2026 event is a new leader: Orlando Watson.

Named the organization's executive director in late 2025, Watson is no stranger to the festival, having performed in past lineups as a lyricist and baritone singer. He also served as JazzFest’s Associate Director from 2019 until 2022. The Cleveland artist brings plenty of experience into his role, having recorded with Academy Award-winning musicians and serving as the senior director of programming at the August Wilson African American Cultural Center, where he managed the Pittsburgh International Jazz Festival and founded the Hooks and Phonics Festival in 2024. Watson is the youngest-ever and the first African American executive director in the festival’s 47-year history.

Tri-C JazzFest is one of the most historic jazz festivals in the nation. Founded in 1980, it was designed to connect students with world-class jazz artists through a vast catalogue of summer programming. Today, the event remains known for highlighting hundreds of jazz musicians over the years and proving that Cleveland can do more than just rock. 

We sat down with Watson to discuss his vision and what audiences can expect at Tri-C JazzFest this June.  

Cleveland Magazine: What does it mean for JazzFest to be its youngest and first African American executive director?

Orlando Watson: It’s all what representation stands for. When I was 14 or 15 years old, studying here at summer camps, I was studying with legendary guys, all Caucasian. I don’t take it lightly. If I had somebody like me, I could see what life could be as an artist and executive, and my world would’ve opened up even more. So, I’m happy to be that, especially in my hometown. 

CM: As a Cleveland native, why is JazzFest important to you?

OW: If you’ve been following me on social media, you’ll see a lot of my posts with #OhioHasIt. I preach that no matter where I go in the world. I never get the feeling I do when I hear live instrumentation anywhere else other than Cleveland. It’s major for me because I know a lot of musicians from Cleveland who really just need a platform, and I see Tri-C JazzFest as that sustainable, trusted platform in this region for artists. I think I have a different stake in the game as an artist myself. I always try to lead programming with the artists in mind. One of the fingerprints I’m aiming to leave on this festival is having opening artists, not just headliners. For example, we got Durand Bernarr, who just won the 2025 (Grammy Award for) Best Progressive R&B Album, but his opening artist is a local legend by the name of Rob Hubbard, whom I used to study with. Hubb is a phenomenal musician.  It’s important for me to highlight things like that. I’m really trying to show the world on a large scale how much Ohio has to offer. 

CM: What was your vision for JazzFest when you took on this new role?

OW: So much. In my mind, I’ve programmed out the next two years. One aspect was elevating the outdoor footprint. We have acquired an Event Planner by the name of Alascia Jones. She’s been phenomenal. We have three different districts — the Family District, the Refresh District and the Spotlight District — and each of those locations will have different activities and guests and things like that. There’s also an educational component with a masterclass by Savion Glover with our dance students here, which is open to the public.

Also, with the artists in mind, we have something called Music Mavericks. I handpicked five artists on this year’s lineup to have a promo code. They can disperse that to the public for 10% off any show, and whatever show the code is associated with, they get a 5% return. It’s kind of an incentive for them to have a vested interest and stake in the festival. It always used to be sort of a “pay to play,” and I always hated that model. We pay the artist their booking fee, but as an incentive on top of that, they have a commission. I’ve never seen a model like that, so I feel like it’s kind of groundbreaking.

It’s also the first time we are including national artists outside. I wanted to create an equitable space that was more accessible and affordable for the community. All of our outdoor options are free. I wanted to create a space where everybody felt equal. We all love music, so that was very important to me. Lastly, in years previous, I noticed that only the national artists were listed on the festival graphics, but I wanted to also include the local and regional artists. I wanted to make the local artists feel seen and included.

CM: You are involved in a lot of cultural policy and advocacy groups. How does that come into play with this project?

OW: I have experience on both sides of the game, as an executive and an artist. I know what’s fair and equitable as an artist. I know the opportunities I’ve been afforded. It’s a core model of mine not to lowball artists. On the executive side, I’m creating programming that is well-rounded, inclusive and diverse. Sheila E. is our opening night artist. She is a middle-aged, Hispanic woman who is a legendary percussionist. How often do you see women playing drums at her level and at her age? Making everybody feel seen and involved is very important to me. 

CM: What changes or creative liberties have you taken that you are proudest of? 

OW: Like I mentioned, incorporating opening acts and outdoor shows. I’m also really excited about our partnership with the Cleveland Cavaliers. Jim Chones, a retired Cavaliers player and broadcaster, will be joining us in the lobby of KeyBank State Theatre ahead of Sheila E.’s concert, playing bass in his trio. We will have the Scream Team, Cavs Girls and mascots. So, I’m really vested in the Cavs winning it all. I’m proud of that, and also just partnering with local organizations who have a heart for the community and don’t mind sharing the pie.

CM: With JazzFest being such a long-standing tradition in Cleveland, is it intimidating to come in and make the changes you’re making?

OW: It’s imperative for me to build on the foundation of traditional jazz while also being progressive and being more jazz-adjacent with experimental artists. It’s all music and it’s all love. Intimidating is not the word. I’m pretty hard to intimidate. I understand the risk involved, but I’m not afraid to make the changes. I just know you can’t please everybody. Not everybody is going to support, but those who do will without excuse. Those who don’t, there may come a time where they swing back around. We’ll be here for another 50 years. Intimidated, not so much. Motivated.

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