Joseph S. “Joe” Loveless Jr., whose careers spanned education, coaching, business and politics, died from vascular dementia June 15 at his Joppa home. He was 84.

“Joe mentored me. I had him as a student and as a football coach at Colonel Richardson Senior High School and when I went into the field of physical education, he was my vice principal at Riverview Middle School in Denton, and we managed to stay friends through the years,” said Richard “Dick” Wheatley.

“He was a good friend and mentor and always there if you needed to talk to someone,” he said.

Joseph Savin Loveless Jr. son of Joseph S. Loveless Sr., a master carpenter and professional Big Band era drummer, and Mildred Rosel Buckingham, a retail clerk, was born at his parent’s Gwynn Oak home.

When he was a child, Mr. Loveless moved with his family to a 22-acre farm in Finksburg where they built a home and leased the land to a farmer.

As a boy, he harvested potatoes and received a nickel a bushel, family members said.

After graduating from Westminster High School in 1958, Mr. Loveless attended what was then Slippery Rock State Teachers College in Pennsylvania, and then transferred to what is now Frostburg University where he played starting center on the school’s inaugural football team.

He earned a bachelor’s degree in education and began his career in education in 1963 teaching health and physical education at Westminster High School, where he was head coach of the junior varsity football team.

He subsequently taught math and science at Arbutus Junior High School, now Arbutus Middle School, until being recruited to be the athletic director and head football and baseball coach at Colonel Richardson Senior High School.

He then went to rival North Caroline Senior High School in Ridgely as varsity defensive football coach, and in 1970, after the legendary Granville “Rock” Harrison retired, took over as head coach.

“As a coach, he was very thorough because he certainly knew the game,” Mr. Wheatley said. “His scouting reports and game plans were very thorough. We learned the game from someone who really knew the game.”

In addition to his coaching and teaching duties, Mr. Loveless earned a master’s degree in education in 1974 from Frostburg.

He moved into administration as vice principal of discipline at Riverview Middle School, now Lockerman Middle School in Denton.

He then returned to Colonel Richardson as vice principal.

“As a principal, he was a good disciplinarian, he always backed his teachers, and was good to the students,” said Mr. Wheatley, who retired in 2003. “And he wasn’t above filling in as a teacher in a classroom if needed.”

Mr. Loveless entered the world of Democratic politics in Denton when he was elected as a town commissioner in 1978, and in 1981, named vice mayor.

In 1982, the town commissioners selected him as mayor, succeeding Richard T. Warfield.

During his administration, he played a role in bringing better housing, helping plan the Denton Industrial Park and other civic improvements.

“They rotate the mayoral terms, which are a year,” said Karin Sonja Remesch, a former Baltimore Sun reporter, and significant other for 27 years.

He organized celebrity charity golf tournaments at the Caroline Country Club featuring Orioles and Baltimore Colts players, was a firefighter with the Denton Volunteer Fire Department, an assistant Little League coach and an active member of St. Luke’s United Methodist Church.

An entrepreneur, he founded Joe Loveless Tires and eventually left education to own and operate the Joe Loveless Service Co., which specialized in estate cleaning.

He sold cars for Jarvis Chevrolet while obtaining his real estate license and worked in commercial development where he urged chains to consider locating their businesses in rural areas.

“His business forte was bringing people together,” Ms. Remesch said.

He retired in 2015 after being diagnosed with vascular dementia in 2014.

Divorced in 1995 from Carol Miller, he met Ms. Remesch two years later.

The couple were inseparable and enjoyed hiking and backpacking in Ms. Remesch’s native Germany as well as in Austria, Switzerland, France and Denmark.

They both attended the Baltimore Symphony Orchestra and travelled to New York several times a year for Metropolitan Opera performances.

“He enjoyed fine wine and candle light dining, but couldn’t even fry an egg himself,” Ms. Remesch said. “He didn’t even know how to turn on a stove but he was a great host at our small dinner gatherings, often seven-course dinners. I did the cooking and he did the dishes.”

She recalled the time she was entertaining several girlfriends and he decided to be the group’s butler.

“He went upstairs, put on his tuxedo, and greeted my guests with glasses of champagne on a silver tray with a crisp white towel draped over his arm.”

Mr. Loveless was an avid collector of classic vintage fountain pens.

“Daily, he would choose a pen for his shirt pocket as carefully as a woman would choose earrings,” Ms. Remesch said. “And they were Mont Blancs, Pelikans or Omas, just to mention a few.”

Plans for a private celebration of life gathering to be held in September are incomplete.

In addition to Ms. Remesch, his life partner of 27 years, he is survived by a son, Joseph S. Loveless III, of Purcellville, Virginia; a daughter, Donna Warner, of Easton; a brother, Johnny Loveless, of Nashville; a sister, Gail Elford, of Florida; five grandchildren; and four great-grandchildren.