"He sat and talked for an hour," Patricia Hess recalled of her husband. "It was very difficult for him, but he was determined he was going to do it."
On Tuesday, Dec. 24, Mr. Hess died at his home in Egg Harbor Township, N.J. He had been diagnosed with liver cancer and end-stage liver disease in May.
Mr. Hess joined the Street administration in 2001 as a deputy managing director for special-needs housing. He worked with advocates for the homeless to craft Street's "Ten-Year Plan to End Homelessness."
"He made the whole issue a priority in the Street administration," said Philip Goldsmith, a former city managing director who worked with Mr. Hess. "For the first time, we had a strategy that was important."
During Mr. Hess' tenure, the city focused more of its resources on reaching out to people living on the streets.
"He made the system focus on the people who were not easy to help, understanding that that was the only way to make progress," said Dennis Culhane, an expert on homelessness at the University of Pennsylvania. During Mr. Hess' tenure, the number of street homeless in Center City was nearly cut in half, he said.
A native of Baltimore, Mr. Hess joined the Army after high school and graduated from the University of Maryland on the GI Bill.
For 16 years, Mr. Hess ran a chain of thrift stores for the Disabled American Veterans in Baltimore. Disturbed by the high number of veterans who were homeless, he began investigating ways to help them and started a nonprofit program that used a military model to work with homeless veterans with addictions.
"He felt the need to do something about it," Patricia Hess said. "He felt a real connection. That's where it first started."
After five years in Philadelphia, Mr. Hess went to work for New York Mayor Michael Bloomberg as commissioner of the Department of Homeless Services. He resigned in 2010 and went to work for the Doe Fund, which ran the Ready, Willing and Able program, a provider of housing and employment for homeless men.
In 2011, Mr. Hess founded Housing Solutions USA, a housing and service provider for homeless people in New York.
Daughter Christi Hess said that when her father learned that he might have only six months to live, she hurried to finish her doctoral thesis and graduate ahead of schedule from the University of Wisconsin in Madison.
She made a week-by-week schedule of what she needed to do. Her father called her every day to check on her progress and make sure she was on track.
"My mom told me that he kept the printed-out schedule next to his recliner in the living room," Christi Hess said in an e-mail.
Weak but determined, he flew with his wife to Madison on Dec. 21. He slept during most of the ceremony the next morning, but stood for the national anthem and clapped wildly when his daughter walked across the stage.
Back in Egg Harbor on Monday evening, he said, "Home," before slipping into a coma.
In addition to his wife and daughter, Mr. Hess is survived by another daughter, Brittany; his mother, Barbara Anne Neumeister Hess; a sister; and a brother.
Friends may call from 2 to 4 p.m. Sunday, Jan. 5, and 2 to 4 and 7 to 9 p.m. Monday, Jan. 6, at Lemmon Funeral Home of Dulaney Valley Inc., 10 W. Padonia Rd., Timonium, Md.
A Funeral Mass will be offered at 10 a.m. Tuesday, Jan. 7, at St. Joseph Church, 101 Church Lane, Cockeysville, Md. Interment will follow at Maryland Veterans Cemetery, Garrison Forest.
Memorial donations may be made to Rob Hess Memorial Gifts, c/o Project HOME, 1515 Fairmount Ave., Philadelphia 19130.