Leading Player Award
The LEADING PLAYER Award honors individuals whose steadfast commitment has shaped the Pittsburgh Playhouse into what it is today. Recipients are recognized for their deep understanding of how community engagement, economic development, and innovative strategy drive our success. With vision, creativity, and integrity, they have played a pivotal role in strengthening the Playhouse and securing its vibrant future.
Please take a moment to check out our past honorees below.

Anne Lewis is a dynamic force in both business and community leadership. Anne stepped into the role of board chair at Oxford in 2007 following the passing of her husband, Eddie Lewis, the firm’s co-founder and CEO. But Anne’s journey as a community leader began long before – and continues to this day. Anne has spearheaded many transformational projects throughout her career, including headline-making initiatives at the Children’s Museum of Pittsburgh, Fox Chapel Country Day School, Shady Side Academy, the Pittsburgh Promise, and Point Park University. A master at fundraising, she has helped raise over $200 million for Pittsburgh’s non-profit community. In 2010, Anne joined the board of Point Park University and served a six-year term as Board Chair. Her tenure was marked by the university’s largest-ever capital campaign, which expanded its downtown campus and included the opening of the $74 million Pittsburgh Playhouse in 2018. Currently, Anne serves as the board chair of the Pittsburgh Promise, as vice chair of the Buhl Foundation, and as a director of The Eye and Ear Foundation. She’s advised and supported countless other organizations in the region.
Anne has been honored with several prestigious awards including Pittsburgh Business Times Women of Influence Impact Award, Heinz History Center’s History Maker Award, and was and being named a Distinguished Daughter of Pennsylvania. In recognition of her impact, the ALS Association named an award after her, the Anne Lewis Humanitarian and Advocacy Award. With a master’s in public management from the Heinz College at Carnegie Mellon University, Anne has been a member of the Dean’s Advisory Council since 2008. Her leadership, vision, and dedication continue to inspire and advance the communities she passionately serves.

As Executive Chairman of PJ Dick, Trumbull, and The Lindy Group, Cliff Rowe is a respected corporate as well as community leader. He employs a hands-on approach to maintaining relationships with project owners and executives and oversees corporate planning and development for PJ Dick – Trumbull – Lindy Group. Cliff has served on several boards and professional organizations, including the Master Builders Association of Western Pennsylvania, Associated General Contractors of America, The General Contractors Association of Pennsylvania, Manchester Bidwell Corporation, UPMC Children’s Hospital of Pittsburgh, and the Children’s Hospital of Pittsburgh Foundation. Cliff and his wife, Diane, have four married children and 11 grandchildren, and make their home in Mount Lebanon.

Dennis Cestra
Dennis Cestra Sr. is Senior Vice President of Howard Hanna Real Estate Services. Dennis serves as the Director of Appraisal Services for the firm and oversees facility management with his wife Annie Hanna Cestra. He is a member of the Appraisal Institute where he earned his SRA designation. He also served as President of the Western Pennsylvania chapter of the Appraisal Institute. He earned his Bachelor of Arts degree from Point Park in 1972. He served as a board member for numerous terms and later elected as Trustee Emeritus.
Dennis holds his Associate Brokers real estate license in Pennsylvania. He is a founding member of the coalition of the Pennsylvania Real Estate Appraisers and served as President of The Pennsylvania Council of Real Estate Appraisers. Dennis was a board member of Mercy Hospital and later became Chairman of Pittsburgh Mercy Health System. He recently served as Vice Chair on the Board of Pittsburgh Central Catholic High School. He was asked to chair the appraisal committee of the Pennsylvania Association of Realtors.
While attending Point Park University, he was elected President of the Lambda Chi Alpha fraternity in 1971.
Annie Cestra
Annie Hanna Cestra, Chief Operating Officer of the largest private real estate company in the United States, is known for her determination and integrity. Headquartered in Pittsburgh, Pennsylvania, Howard Hanna Real Estate Services is a family-owned company with three generations of the Hanna Family involved in the day-to-day operations.
Annie was named Chief Operating Officer of Howard Hanna Real Estate Services in 1986, after 12 years of serving as Treasurer and guiding the fiscal policies of the company from the beginning of its remarkable expansion. She holds a Bachelor of Arts degree from Georgian Court University and a Master of Education degree from the University of Pittsburgh and an honorary Doctorate Degree in Business Administration from GCU. Annie currently holds a Real Estate Broker and Insurance license in the Commonwealth of Pennsylvania, Ohio and New York.
In December 2025, Pennsylvania Governor Josh Shapiro appointed Annie Chairman of the State Real Estate Commission. She also has served as a Director of the Realtors Association of Metropolitan Pittsburgh’s Executive Committee and a delegate to the Pennsylvania Association of Realtors.
An active and involved member of the community, Annie is currently a member of the Duquesne University Board of Directors. She is a past Chairman of the Board of the Urban League of Greater Pittsburgh. She has served as President and Vice President respectively of St. Lucy’s Auxiliary to the Blind and of Pittsburgh Hearing, Speech and Deaf Services. She also has served on the Board of the Winchester Thurston School and as Treasurer of Fox Chapel Country Day School’s Board of Trustees.
The National Relocation and Real Estate Magazine honored Annie as “One of the Most Powerful Women in Real Estate”. Carlow College recognized Annie as a “Woman of Spirit.” She was also honored in Washington DC at the Second Annual Working Woman 500 Congress. Annie received the 2024 Women of Influence award from Pittsburg Business Times.
Annie and her husband Dennis reside in Pittsburgh Pennsylvania, where they raised their three children.