In 2004, a national news show aired a piece on Reagan's work. The next day, an Iraq War widow from Boise, Idaho, called him and asked how much he would charge to do a portrait of her late husband.
He told her there would be no charge; just send him a photo. When the woman called back to thank him for the sketch, he was overcome with emotion.
Reagan turned to his wife and said, "We need to do them all."
Thus was born the Fallen Heroes Project. At the beginning, a general asked whether Reagan understood what he had gotten himself in for. Reagan replied that he figured the wars would last five years, and that he would have to no more than 1,500 portraits.
He has done 3,100 so far. And every day, he gets at least one e-mail, requesting another.
"I haven't drawn 3,100 portraits," he says. "I've drawn one. ... Every one is too many for me."
The 65-year-old artist wakes around 4 a.m. each morning. He "cooks" his coffee, feeds his cats and sits down at his drawing table.
Each portrait takes about five hours, though some take longer and he has done as many as four in one day to have them ready in time for funerals or memorial services. He walks five miles each night, "to just be able to get air back in me."
Reagan works from videos and favorite photos — some showing the person in civilian life. People send him letters and diary entries from the deceased.
"So when I draw," he says, "I feel like I'm having a conversation."
When Lisa Freeman wrote to ask that he draw her son — in his Marine dress blues — she passed along a note from one of Matthew's high school classmates, who recalled the young man who listened so well he made you feel "like you were the most important person in the world."
"I believe the world and the lives he touched are better for him being here," she wrote.
Joshua Welle was president of the Annapolis Class of 2002. But there were 980 midshipmen, and though he had heard of Freeman, he did not know him — until after his death.
Welle, a lieutenant commander in the Navy, is back in the States for three weeks' leave. He is using part of that time to travel the country and tell audiences about Freeman and other classmates who have sacrificed in the ongoing War on Terror.
The surface warfare officer is lead editor of a new book, "In the Shadow of Greatness: Voices of Leadership, Sacrifice, and Service from America's Longest War." Of the Class of 2002, four have died in combat, one lost both legs, and another won the Silver Star.
As he crisscrosses the country, Welle senses that "the American people have fatigue" about the war in Afghanistan. It has become part of his mission to remind them why our troops are still there, that the war serves to protect the United States. "Americans need to have a long view," he says
Welle says he and his coeditors wrote the book "to tell a story of post-911 leadership and help America understand that there is a good news story coming out of Iraq and Afghanistan, even though there's no clear victory."
He adds: "I don't think we can look at the wounds of battle in a body count and a death toll."
Proceeds from the book — and, by extension, from Matthew Freeman's story — have helped causes to make a difference in the lives of Afghan War vets, including the Challenged Athlete Foundation's "Operation Rebound," a sports and fitness program for wounded veterans and first responders with permanent physical disabilities.
Wounded veterans like Daniel Riley.
When Riley joined the Marines in 2007 at age 21, he was "fully aware it wasn't a question of 'if'; it would be a question of when I would find myself in Iraq or Afghanistan."
He made it unscathed through his first tour, in Iraq. And, as he'd expected, he soon found himself in Afghanistan.
On Dec. 16, 2010, Cpl. Riley and his infantry squad were on a dismounted patrol to clear a compound in the Marjah district of then-hot Helmand Province. The men had found and disarmed a couple of IEDs.