Thomas Patrick ‘Tommy’ Oswald, a software sales manager known for his courage and friendly disposition, dies at 25

Thomas Patrick “Tommy” Oswald, a software sales manager recalled for his selfless personality and personal courage, died May 28 at his Homeland residence. He was 25.

In 2021, Mr. Oswald was diagnosed with a rare pediatric bone cancer, Ewing’s sarcoma, a condition that affects young adults and children.

“Tommy leaves a legacy of courage and good deeds,” said Dr. Aaron Rapoport, a physician with the University of Maryland Medical Center.

Born in Baltimore and raised on St. Dunstans Road in Homeland, he was the son of Christopher T. Oswald and Jeanne M. McDonough.

He attended St. Pius X School on York Road and played basketball, soccer and baseball. Mr. Oswald was a 2015 graduate of Loyola Blakefield. He played lacrosse and was awarded the school’s Loyola Alumni Award, given to the senior “who is most conspicuous for school spirit, leadership, and excellence in studies.”

“Tommy was authentically good and was authentically kind,” said Anthony Day, Loyola Blakefield’s president. “He was a selfless young man.”

David Gately Jr., a childhood friend, said: “Tommy was loyal and caring. He had high energy and was funny. He was a master conversationalist. He was good at walking up on the spot and being able to talk to people. Even at the peak of his cancer, and he was fighting for his own life, he sat there and asked me about my life. He was inspirational about being there for others.”

1 of 72

Georgia Clark Sadler, a trailblazer for women in the military and the Naval Academy’s first female instructor (handout)

He earned a bachelor’s degree in history from Towson University. While at the school he was named a presidential ambassador, and was one of 20 students who assisted the university’s president in philanthropic and fundraising events. He was a member and past president of the Alpha Sigma Phi Fraternity.

“Tommy had a gregarious personality, extended positivity and enthusiasm for life to his family and many cherished friends in shared life experiences and memories,” his father said. “Tommy was a collector of relationships and friendships in life, young and old.

While in high school, Mr. Oswald became an advocate for the Claire Marie Foundation, a Baltimore-based charity that raises awareness and offers education to prevent adolescent and young adult melanoma. The foundation is named for Claire Wagonhurst, a Notre Dame Preparatory School senior who died in 2014.

“Tommy was a remarkable young man who came forward and engaged with me and my husband, Rocky, shortly after our daughter died,” said Marianne Banister. “He was a key organizer for a dance-a-thon, Moves for Claire, while he was a senior at Loyola. He and others raised $24,000 to help start our foundation. He connected intently with our organization and later he himself later was diagnosed with cancer.”

She said he was named an ambassador for her organization and worked to prevent melanoma on the Towson University campus while he was a student there.

“I just loved this young man. He impacted so many people with his kindness. Everyone wanted to be around Tommy,” Ms. Bannister said. “Post-college, he remained active on the Claire Marie Foundation junior board.”

A former neighbor, Tom Marechek, recalled Mr. Oswald: “He was a caring, respectable kid. He was a mature young man and my sons asked to have him as their babysitter. ... He was somebody we could always trust.”

While in college he was an intern for the Baltimore Orioles. He later was in sales for the MassMutual-Thompson Financial Group and became a government sales representative at Carahsoft.

Mr. Oswald moved to Savannah, Georgia, in 2021 and later settled in Charleston, South Carolina. He was an account manager at Workiva, a software firm that manages and analyzes business data, and won sales awards in his field.

1 of 152

Anita Pointer, one of four sibling singers who topped the charts and earned critical acclaim as The Pointer Sisters, died Dec. 31, 2022, at the age of 74, her publicist announced. (Phil Mccarten/AP)

“Tommy was a good problem solver and that good in him also proved good in business. He listened to you and had empathy,” said his friend Mr. Gately.

The Morning Sun

Daily

Get your morning news in your e-mail inbox. Get all the top news and sports from the baltimoresun.com.

Mr. Oswald was a fan of the Orioles and Ravens. He was a Swallow at the Hollow softball team outfielder and a St. Pius X basketball coach.

He played golf at Pine Ridge, Fox Hollow and Clifton Park. He also played at Kiawah Island’s Ocean Course and later told friends it was the best course he ever played.

After his diagnosis, Mr. Oswald was treated at the University of Maryland Medical Center. He was a patient of doctors Aaron Ciner and Aaron Rapoport.

Dr. Rapoport said: “He was a hero to me because he accepted this challenging diagnosis and embraced the treatments and opportunities for a cure with energy, enthusiasm and gusto. He worked back from many setbacks.

“When told by rehab people he would not be able to walk, he came back, all inspirational and upbeat. We had collected stem cells for a treatment for him, but he did not respond to further therapy. Tommy was truly one of the most courageous young men I have ever met.”

[ Dr. Constantine J. ‘Connie’ Sakles, an expert in psychodrama, dies ]

Survivors include his parents, Christopher T. Oswald, executive vice president of the Farmers & Merchants Bank, and Jeanne M. McDonough, purchasing agent for Aumen Asner Interior Design; a brother, Alex Smith of Harrisburg, Pennsylvania; a sister, Kelly Oswald of Baltimore; and aunts, uncles and cousins.

A visitation will be held from 2 p.m. to 8 p.m. June 17 at the Ruck Towson Funeral Home at 1050 York Road. A memorial service will be at 5:30 p.m. June 18 at Knott Hall at Loyola Blakefield at 500 Chestnut Ave. A reception will follow.