A Legacy of Convening: Reflecting on the Service of El Pomar’s Theophilus Gregory
By Megan Sanders
Starting in January 2021, Theophilus “Theo” Gregory will be transitioning out of his role as Senior Vice President of Outreach at El Pomar Foundation, after more than 20 years. El Pomar is grateful for Theo’s contributions to the Foundation and to the greater Colorado Springs and Pueblo communities.
Reflecting on his time working at El Pomar Foundation, Theo says humbly that he does not have a legacy. However, after two decades of work at the Foundation, he clearly embodies one of El Pomar’s core roles, that of a convener. Since he joined the Foundation in 1998, Theo has used his role at El Pomar to connect communities and individuals in Colorado Springs and Pueblo through a steadfast belief in service, stewardship and hope.
According to Theo, his ability to convene effectively comes from decades of experience in intercollegiate athletics and higher education, beginning when he was a doctoral candidate at Ohio State University. Because of his wisdom and approachability, the football team recruited him to speak with parents of potential recruits, knowing he was the perfect person to inspire people to join the team. Theo moved through his years at higher education institutions with a strong work ethic and an infectious confidence, traits he was taught by his mother and father. He reflects on a time when a co-worker told him he walked like he owned the Earth, to which he said, “nobody ever told me I didn’t!” Theo’s warm confidence is one of the many ways he made others feel welcome as he took on different roles at the University of Nevada, Las Vegas, University of Colorado at Boulder and the University of Colorado at Colorado Springs, where he started the intercollegiate athletics program.
Although Theo loved working in higher education and anticipated continuing his career in that field to empower young people in communities across the country, he took a self-described “leap of faith” on El Pomar in 1998. With the broad job title of Senior Vice President of Outreach, which encompassed a variety of charges from the Foundation’s Trustees, Theo was at first unsure of his role but was eager to get to work. When he started, Theo was tasked with various large projects supporting Seniors in Service, Rocky Mountain State Games, the Karl E. Eitel Fund, and the Empty Stocking Fund. He also spearheaded El Pomar’s youth development strategy supporting the Boys and Girls Club and he directed the El Pomar and Denver Broncos Football Club Health and Wellness Partnership.
Theo has conducted his work with El Pomar much like he did in previous roles in higher education and athletics, by bringing people together to discuss civic leadership and the ways in which they can serve their community. Through each of his projects, Theo developed relationships with leaders across the state and conducted site visits at nonprofits El Pomar supported. Through community impact surveys, Theo and others at the Foundation realized the need to improve El Pomar’s community stewardship within Colorado Springs and Pueblo to ensure the Foundation was reaching out to all relevant communities and broadening the impact of its grant making and programmatic work.
Part of that vision included better engagement with leaders from communities of color in Colorado Springs and Pueblo. Although several organizations at the time extended outreach to communities of color for participation in community leadership development programs, these programs were not as well attended as they had been more recently.
In assessing the participation trends, Theo identified that certain programs felt inaccessible. Seeing this challenge to stewardship, El Pomar Trustees established the Emerging Leaders Development Program (ELD) in 2001. The objective was to convene individuals of color and remove barriers to leadership development by bringing attention to opportunities and making them broadly accessible. Theo was named Director of the program. ELD was designed to empower emerging ethnic minority leaders by encouraging them to invest in personal and professional development trainings and engage in their communities.
Theo says ELD is not a leadership program but rather a program designed to provide the space, strategies and support to those who want to lead. In short, ELD is a program designed to convene, empower and take action. The program hosts quarterly meetings at Penrose House to discuss leadership trainings and professional development opportunities, connect participants with successful leaders through panel and networking sessions, and encourage participants to serve their communities through board leadership. Where cost is a barrier to those opportunities, ELD offers scholarships.
Over the past two decades, more than 400 participants have completed community leadership development programs, fulfilling what Theo describes as the pathway to broad-based community involvement, civic engagement and serving on nonprofit boards. In addition, the ELD Advisory Council connects more than 1,000 community members with ELD participants to discuss and learn more about opportunities for service. With so many successful alumni of the ELD program, including current El Pomar Trustee Andrea Aragon, El Pomar has strengthened relationships with communities across Colorado Springs and Pueblo.
While those living leaders are a key part of ELD, Theo has also worked to honor the legacy of community leaders of color in other ways. In 2006, El Pomar’s Chairman William J. Hybl renamed one of the rooms in El Pomar’s Penrose House, the Milton E. Proby Cultural Heritage Room, in honor of the revered local civil rights activist. The room now preserves the legacy and documents the contributions of African American, Asian, Hispanic/Latino and Native American individuals from southern Colorado through an annual reception and dedicated plaque.
Much of ELD’s success is tied to Theo, whose long experience in higher education and intercollegiate athletics taught him the value of serving others while ensuring everyone can connect on a level playing field. When ELD participants walk into Penrose House, Theo believes they feel welcome.
His advice to others is to maintain resilience and hope inspired by others. He says that there will always be people in our lives who will move us to act and be a certain way. He adds that it is important to remember these influential voices during challenging times, as they provide hope, courage, and new perspectives. When we have the courage to do something, he also advises to maintain a sense of stewardship and loyalty to our work and to our communities.
In that spirit, Theo hopes to continue to serve El Pomar and the Colorado Springs Sports Corporation for the next few years. The Colorado Springs Sports Corporation serves to “attract, retain, and support local, state and national sports organizations, businesses and…exemplify our dedication to make Colorado Springs a sports destination as ‘Olympic City USA.’” Theo also hopes to take more time to fulfill his passion for sports out on the golf course. El Pomar is grateful for Theo’s stewardship of the Foundation’s mission, established by Julie and Spencer Penrose, to enhance, encourage and promote the current and future well-being of the people of Colorado.