Kelly was a captain back then. He asked questions back then. Hearing 20 years later that Kelly's new boss talks about his innovative mind and ability to command others, his former classmates have a dash of "I told you so" in their voices.
"He was always drawing plays up like a sandlot quarterback," said Phil Hebert, 49. "And he expects [people] out of his group to question him, to do it a better way. He gets everybody thinking. Always."
Bob Leonard, 63, was Kelly's high school football coach. They discussed Kelly's future when Kelly was in high school. Kelly wanted to coach, and he eventually joined Leonard's staff at Manchester Central.
A few weeks ago, Leonard watched an Oregon basketball game. Kelly, then the Oregon football coach, stood in a tunnel focused on the court when the camera locked in on him.
"I looked, and I said: 'He's not watching the game. He's watching the speed trying to figure out how he can get something that's out there put into the offense,' " Leonard said. "He's always looking."
From the beginning, Leonard said, Kelly understood the advantage speed provided. As a quarterback, Kelly had quick feet that reminded Leonard of former NFL quarterback Fran Tarkenton. Manchester Central ran an I-formation, and the plan was to use a fullback and the linemen to "shove you off the field." But with Kelly, they ran a bootleg series.
"He could do so many things when he got around that corner," Leonard said while driving the one mile down Beech Street from Manchester Central to Gill Stadium, the same path the band used to march on Friday nights before Kelly's games.
When reminiscing about Kelly's skills, Leonard focused on his former player's role as a safety. Leonard devoted his attention to the defensive front because he knew Kelly would take care of the backfield.
"He was always there. I didn't have to worry," Leonard said. "I always had a safety who was going to be where he's supposed to be. That's what his strong point always was in high school. The job got done."
Once the job was finished, Leonard said, Kelly would have questions. He saw the game in slow motion and wanted to dissect what happened.
Because Kelly is 5-foot9, Leonard initially thought he would go to Division III Colby College. Kelly instead attended Division I New Hampshire, determined to learn more about football. He wanted to see new ideas, and a better program afforded him that chance. It was part of an education that is ongoing.
"He's just so smart," Leonard said. "It's awful when a coach thinks his kids are smarter than he is, but he was. He had that ability to look at what was happening and do some things. And he motivated other kids."
Hebert remembers that Kelly was not a standout hockey player. He was a "third-line grinder," Hebert said. But he maximized his ability. Fellow athlete Karl Alterman said Kelly was always the captain, picking the teams during recess.
And in big moments, Kelly could be trusted. If Kelly was put on a track and asked to run straight, Leonard said, Kelly would not have run very fast. But put him in a relay race when others on his team depended on him, and "he found something else."
Kelly did not devote his time to only football. There were few one-sport specialists. He competed in football, then hockey, then track and field.
"Super competitive at everything," Hebert remembered.
And then Kelly would study the game. His classmates and coach remember him as an avid film watcher, searching for every advantage. And he did not look just for what to do but why to do it.
"He's not going to do things because somebody else said it's a good idea," Leonard said. "That's why he never got in trouble. Because everything gets thought out."
That was partly the byproduct of being from a family in which the father was a lawyer, Leonard said. Kelly was not afraid to question things, to find a better way. That's how he built an offense at New Hampshire. He saw that fullbacks were hard to find, so instead of forcing the issue, he created a better solution. That turned out to be Kelly's version of the spread offense.
"He can teach the game of football better than anyone you've ever met," Leonard said. "He looks at the player and says, 'What can I expect from you?' And he expects a lot. But he doesn't expect anything more than what that young man can do."
It's lunchtime at the Red Arrow Diner, where the front door is marked by the famous guests who have eaten there, from Paul Newman to Mitt Romney. If Kelly wins a Super Bowl with the Eagles and returns home for some chili, maybe his name will appear on the door.
Yet, whether Kelly became the coach of the Eagles or an assistant at Manchester Central, he's one of the players Leonard said he would have remembered. Kelly always smiled. He kept out of trouble. He demonstrated ambition.
"Never had anyone say a bad word about Chip Kelly," said Leonard, who has lived in New Hampshire his whole life. Then Leonard thought about all the players he coached and what they went on to become in life.
"I coached doctors. I coached lawyers. I even coached a priest," Leonard said. "When he got to Oregon I said, 'And now a college coach.' This is pretty good for a kid who grew up in Manchester, went to the University of New Hampshire, coached for a bunch of years in town."
Later, at the bar called the Back Room where some of his some old classmates were gathered, similar sentiments flowed. They don't need to buy the Pac-12 network anymore, either.
Karl Alterman went to school with Kelly from elementary school through college. Whenever he'd see Kelly on TV, he'd watch to see if something about Kelly changed. Alterman could never find a thing.
"Didn't have an enemy in the world," Hebert said. "Everybody loved him. Still do. Wish he was here now. I'd give him a big hug."
Kelly returns to Manchester and different parts of New Hampshire during the summer. It's the biggest city in the state, so it's not the type of place where everyone at the diner knows you. But they take pride in their own. And in the corner of the bar on a Saturday afternoon, they take pride in Kelly.
"When you get in hot water here, somebody's going to cover your back," Hebert said.
And when somebody makes it big?
"We'll celebrate with champagne," he said.
Last weekend, it was with cold beers. "Chipper" is in the NFL.
Contact Zach Berman at firstname.lastname@example.org. Follow on Twitter @ZBerm.