Tales of equipment donated to a former player who needed cleats for an NFL Europe tryout; or of money loaned to friends who couldn't make the mortgage or had a start-up business idea. A long list of coaches, from Penn State's Bill O'Brien to the Buffalo Bills' Doug Marrone, cite O'Leary as a mentor and major influence on their careers.
"He's helped a lot of people in his life, and he's not the type to talk about it either," said Tom O'Leary, George's youngest brother. "In that respect, I think he reminds me a lot of my father."
Ralph Friedgen, the former Maryland coach who worked with O'Leary at Georgia Tech, added, "George has a hard core but a deep heart. People don't understand that about him. He's very, very generous. I think he's very compassionate."
It's a privilege to see this side of O'Leary. He puts up a shield in public, letting no one inside of his circle unless he's absolutely certain they belong. Jamie Reynolds calls it a "sizing up" period, those weeks and months when O'Leary waits to see, "if you'll extend the same loyalty to him that he's getting ready to extend to you."
Players usually don't see the other side until after their college careers are over, when the bellowing coach becomes the doting advocate.
The disparity between the two sides can be exasperating for those closest to him.
"It bothers me because I want everybody to know what he's like," said Sharon O'Leary, the coach's wife who has endured all the slights by his side.
But they understand O'Leary has a purpose behind being "Coach," and so they leave it alone.
"I am who I am," O'Leary said. "I've always been pretty much like that as a coach. Business and what you do for pleasure are two different things. You can't be the same person."
'George never backed down from anyone'
O'Leary formed his tough outer shell in the Jacob Riis projects on the Lower East Side of Manhattan.
Days in the city in the 1950s were spent playing whatever sports you could find, mostly stickball and basketball. The O'Leary boys' games were interrupted only for dinner or, on some nights, by calls from their mother to return home and say the family rosary. The older O'Leary boys — George, Peter and Terry — learned to pray quickly.
Peter O'Leary recalled walking home one day and discovering his younger brother in a fight in the streets. He tried to jump in, only for George to push him out.
"You grew up being able to handle the street and being able to handle the people who gave you a hard time," said Peter O'Leary, who became president of the Suffolk County Detectives Association. "George never backed down from anything."
The O'Learys moved to Central Islip on Long Island when George was 11 years old, and there he became known more for his charm and athletic ability than fisticuffs.
O'Leary grew up playing three sports, but he gravitated to football. On the island, there was plenty of space for games and O'Leary would find them wherever he could. He would join boys playing eight-on-eight tackle football on the lawn of a mental hospital near his home or on any other patch of green deemed large enough for a game.
At Central Islip High, O'Leary played quarterback and led the team to an undefeated season his senior year. He was lean and muscular then, "not skinny," he said, and the team was good. It would go on a 39-game unbeaten streak, and gave up just six points his final year. O'Leary made all-league and all-county.
Family was packed into the O'Leary home on Long Island, and there was just one bedroom for the four boys. O'Leary's father, also named George, was rarely home. He worked two or three jobs at a time, including the night shift at an aviation plant and during the day at the post office or sometimes as a janitor at the local schools. O'Leary's mother, Peggy, instilled her Irish Catholic beliefs, taking the kids to church often. Family and religion mattered most in the O'Leary home.
George's father would eventually be appointed postmaster and also served as president of the school board.
"It was eight of us and we all didn't suffer because of the upbringing we had," Peter O'Leary said.