Tony-Winning Producer Harold Wolpert Appointed Managing Director of The Cape Playhouse

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Wolpert, founder of My Purple Crayon Advisors, joins artistic director Eric Rosen at the Dennis, MA theater.

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Eric Rosen , Artistic Director of The Cape Playhouse has announced announced that veteran, award-winning arts administrator Harold Wolpert has been appointed the Playhouse's new Managing Director. Wolpert's company, My Purple Crayon Advisors, has been engaged by the Playhouse and will continue to operate.

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Artistic Director Eric Rosen said “The Cape Playhouse is in the midst of one of the most dynamic turnarounds in the theater world, just in time for our Centennial in 2027. Having Harold join me as managing director is a key part of that transformation. We've both been doing this work our whole careers - and bringing his wisdom and passion to the Playhouse sets us up for an extraordinary future - for next year's celebration and for the next century.”

Harold Wolpert said "I had no intention of running a theatre again but The Cape Playhouse has been part of my life since long before I ever imagined a career in the theater. I spent every summer on the Cape when I was growing up and even interned at the Playhouse while going to nearby Camp Kirkland. To return now, as the organization approaches its Centennial, feels like a remarkable full-circle moment.

Through My Purple Crayon Advisors, I have the privilege of working with organizations at pivotal moments in their history, and few opportunities are as exciting as this one. Working alongside Eric, a deeply committed Board, and a community of generous supporters and dedicated audiences, I look forward to building on the Playhouse's extraordinary legacy and ensuring it thrives for generations to come."

Harold Wolpert is a visionary arts leader, teacher, and three-time Tony Award–winning producer and executive who is widely regarded as one of the nonprofit theater field's most respected leaders and strategists.

He has led celebrated organizations including Roundabout Theatre Company, Manhattan Theatre Club, Signature Theatre, and Alley Theatre through periods of significant growth, complex organizational challenges, and transformative change, helping strengthen operations, improve organizational resilience, advance mission impact, and position organizations for long-term success. Throughout his career, he has collaborated with preeminent theater artists on more than 250 Broadway, Off-Broadway, and LORT productions, including three Pulitzer Prize–winning and five Tony Award–winning works, as well as West End and Venice Biennale productions, national tours, transfers, international collaborations, and HD films.

In addition to his work as an arts executive and consultant, Harold has a long history as a teacher and mentor. He currently serves on the faculty of Yale's David Geffen School of Drama, where he helps prepare the next generation of arts leaders. His contributions to the field have been recognized through teaching awards and the Edith Oliver Award for Sustained Excellence in Off-Broadway Theater. His commitment to service extends beyond the theater field and includes a decade of volunteer work with The Trevor Project, the leading suicide prevention and crisis intervention organization for LGBTQ+ young people, as well as service as Board Chair of AIDS Foundation Houston.

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_Originally reported by [BroadwayWorld](https://www.broadwayworld.com/boston/article/The-Cape-Playhouse-Names-Harold-Wolpert-Managing-Director-20260616)._