"Back then there was nobody around, I'm the only photographer there at this morning meeting, unlike today where you'd get a whole bunch. In the early 80's this is the way the campaign was," Cole, a photographer for the Associated Press, told CNN. "I'm almost in his cup of coffee."
Reagan, of course, would eventually go on to be elected president, with Bush as his Vice President.
Cole is still chronicling retail politics in New Hampshire. He is part of the pack of photographers who trail presidential candidates around the state in the lead up to the first-in-the-nation primary. But he's got more experience than most.
You've seen his photos everywhere - shots of Donald Trump waving to supporters and Hillary Clinton grasping a microphone at a town hall. They're on websites, in newspapers and flashing on TV.
Today the campaign trail can be chaos, with gangs of photographers and reporters squeezing into tiny quaint New England diners as candidates look to connect with voters any way they can. However, it's still far more access than the media will have after the New Hampshire primary.
"Once they leave New Hampshire, most of the campaign -- they call it a tarmac campaign -- which means the candidates will fly to an airport and get off the plane, go to a podium, speak to a large crowd, and then they get back on the plane and go to another city," Cole said.
Even with the access the Granite State allows, it can be tough to capture a photo that looks different from the rest. Cole is always on the lookout for something to set his photos apart.
"What I try and do is try to see what the possibilities of what the candidate might do, and I try find things that look New Hampshire, New Hampshire primary style, I try to set myself up for those," Cole says. "So instead of just getting in front of a candidate and walking with them the whole time he's in there, I set myself up in a spot and I wait for the candidate to show up."
Back in September, Cole spotted former Florida Gov. Jeb Bush getting ready for his town hall in Bedford outside of the main event space.
"I saw that Bush was outside so I ran through the door past him and turned around, and right as I turned around he started stretching," Cole said of the photo, showing Bush swinging his arms behind his back, chin raised to the ceiling.
Another moment presented itself at the Hopkinton Fair in September, when New Jersey Gov. Chris Christie got up close and personal with Topper, a Scottish Highland steer.
"I knew when she brought the steer out and he started walking towards it, it had potential for something coming and I was ready for it," Cole said. Christie later told Cole he loved the photo and thought it was funny.
As the primary season heats up its not unusual for candidates to be attacking one another just miles away on the campaign trail in New Hampshire. But with all the time Cole has spent with them on the trail, he sees a different side.
"Generally they're all nice people. When you're not thinking about what their policies are as human beings most of them are all nice," Cole said.