Timothy Healey

Tim Healey began his career as a teacher and coach at Woodbridge Senior High School in 1989. He was hired at Osbourn Park as an Assistant Principal in January of 1997 and became Principal on July 1, 1999, a day after his 32nd birthday. He served as Principal of Osbourn Park for 11 years, until June 2010. Dr. Healey was promoted to Associate Superintendent and worked in that position for five years. He was later selected to be the first principal of Colgan High School when it opened in 2016, a role he is still in currently.

During Dr. Healey’s tenure as principal of Osbourn Park, the Yellow Jackets won 87 District Championships, 30 Regional Championships, and three State Championships - the most successful span of athletic championships in school history.

Partnering and collaborating with the Athletic Booster Club, fellow OPHS Athletic Hall of Fame members, Athletic Director Dan Evans, and Athletic Boosters Leader Mike Holupka, Dr. Healey led Osbourn Park athletics to a period of rejuvenation and unprecedented excellence. 

Motivated by these achievements, Dr. Healey and Dan Evans continued to facilitate positive relationships with Mike & Kathy Holupka that led to the family donating $500,000 to the school in the form of building a new 4,000 square foot fitness facility and a $200,000 donation to renovate the concession stand, add new bathrooms, and renovate the entrance to the main stadium field.

Dr. Healey was twice awarded the “Educator of the Year” by the Osbourn Park Faculty and Staff. In 2006-07, he was named a finalist for both The Washington Post Distinguished Educational Leadership Award and Principal of the Year in Prince William County Public Schools. Two years after he left Osbourn Park, Dr. Healey was invited back by the Class of 2012 to serve as their commencement speaker.

Dr. Healey was named the Virginia Student Council Association’s Principal of the Year in 2021 and served on the Board of Directors for the Virginia Association of Secondary School Principals (VASSP), where he was elected President during the 2020-21 school year. In 2023-24, he was once again a finalist for the Prince William County Schools’ Principal of the Year award.

Tim and his wife, Nicole, continue to live in Prince William County and have three adult children, one of whom is a 2016 graduate of Osbourn Park. Dr. Healey has great memories of his children growing up around Osbourn Park. During his tenure it was normal to see the Healey children accompany their dad on the sidelines of games and in the gym during competitions.

Dr. Healey ingrained the saying, “Once a Jacket, Always a Jacket,” originated by Mike Holupka, into everyday life at OP and ensured its continuation as a tradition by ending his yearly graduation speech with the saying, reminding the new OP Alumni that they would always be Yellow Jackets. He is proud to believe that about himself to this day.