Rick Kiley ’63, Grateful for a “Second Chance,” Gives Back with a Bequest

Richard B. Kiley ’63 Richard B. Kiley ’63 came to Cheshire Academy as a high school sophomore after having a tough freshman year at his previous school. Grateful for the “second chance” at high school and the education that led to a successful career in financial services, Rick and his wife Patti give to Cheshire annually and are giving back with a bequest in their living trust.

“A living trust is certainly an easy way to give: Everything that we have passes to our children, except for three equal amounts to three different schools—one of them Cheshire,” Rick says. “We’re not going to miss the money, but we’re not taking a lot away from our kids either.”

Rick grew up in New Jersey, and family friend Steve Kuk got a teaching job at Cheshire and suggested it to his parents. In addition to improving his academics at Cheshire, Rick played soccer and was on the track team and in the glee club.

“It was a pretty cool deal: Let’s say you took algebra 1 at another school and didn’t fare well, maybe got a D,” Rick explains. “You could take it over in one semester at Cheshire and get that credit behind you. The school was very generous in that regard. And the small classes were very helpful—only six boys in a class.” Campus life made Rick appreciate “the camaraderie among the students” during his time at CA.

He particularly lauds English teacher Carleton Castle. “I got a lot out of English literature with him and found that I had a knowledge of The Great Gatsby and those kinds of books that many people I went to college with did not have,” he says.

Rick started college at Farleigh Dickinson University in New Jersey but was drafted by the Army and sent to Vietnam. He served in the 101st Airborne Division, rising to staff sergeant in the infantry and earning a Bronze Star and an Army commendation.

Upon his return to the States, Rick went back to Farleigh Dickinson—earning a bachelor’s degree in 1973 and a master’s in business administration in 1981. He worked for a number of financial services companies, including Prudential, TIAA-CREF, and a subsidiary of City Group. He earned his CPA in 2005 and retired in 2015. He and Patti, who married in 1972, now live in New Mexico and are enjoying their three grandchildren—and have created college savings plans for all of them. He looks back fondly on his Cheshire years.

“Cheshire had a lot of boys who needed a second chance academically, and it makes you feel very grateful to get that chance,” he says. “I’m what they call a ‘constant giver’—we contribute annually. I would hope that all those who have a positive memory of the school would realize that private schools cannot survive on tuition alone and that upon their passing they can probably afford to give to the school without disadvantaging their heirs.”