A pediatrician, Chessare earned his medical degree from the University of Rome in 1979 and completed his pediatric residency at the University of Massachusetts Medical Center, where he served as chief resident in pediatrics.
Chessare then completed fellowship training in General Academic Pediatrics at Boston Children’s Hospital/Harvard Medical School and earned his Master of Public Health in Medical Care Organization from the University of Michigan School of Public Health.
During his 30-plus years as a health care executive, Chessare has held positions at the Boston Medical Center/Boston University School of Medicine, Albany Medical Center/Albany Medical College, the Medical College of Ohio, and the Caritas Christi Health Care System’s Caritas Norwood Hospital, a 264-bed hospital in the Boston suburb of Norwood.
He was named president and CEO of the Greater Baltimore Medical Center Healthcare System, a private, not-for-profit system based in Towson, in June 2010.
Chessare’s proudest professional achievement, he said, came in 2020 when GBMC was given the Malcolm Baldrige National Award for Performance Excellence. The award was created by Congress to honor role-model businesses.
The most important life lesson he has learned, Chessare said, is “those without handicaps need to look out for those who have them.”
In his off-hours, Chessare likes to jog and go to jazz concerts with his wife. “I am in awe of talented musicians,” he said.