"I did not have much direction at that time ...," Hershey said. "I wasn't a particularly good student. I wasn't interested. I wasn't dedicated."
It was after he enlisted in the Air Force during World War II, sometime during a 25-month tour in Italy, that his outlook changed.
The Hershey of today offered this snappy analysis: "I think I saw the officer lifestyle," which was more appealing than the enlisted man's lifestyle.
He punctuated his thought with one of his bolts of laughter, which magnetically pull you into the humor of the moment.
The hearty laugh signals the Jack Hershey people know, probably for his globetrotting adventurousness, camaraderie or financial wizardry with the investment banking firm of Ferris, Baker Watts Inc. in Hagerstown.
For being a man neither egotistical nor shy about hundreds of thousands of dollars he and his wife have given and promised to community causes.
"I became a committed fellow ...," said Hershey, 80, a lifelong Hagerstown resident. "I believe strongly in being committed to wife and family. I believe strongly in being committed to work. I believe strongly in being committed to contributions to your community.
"Where do they rank? They all rank No. 1."
Which helps explain why today one more thing is true: Hershey is The Herald-Mail's 2005 Person of the Year.
For the purposes of this award, Hershey's philosophy is best examined in reverse order - especially with breaking news on the "contributions to community" front.
On Dec. 20, Hershey and his wife, Anna Leiter Hershey, reached an agreement to give $250,000 to a capital campaign for a new Washington County Hospital.
A matching grant by the Waltersdorf/Henson Endowment Challenge will make the gift worth $500,000.
The result will be The Jack and Anna Hershey Education Center, as it might be known, a place for classes and seminars for the public and training sessions for Washington County Health System employees.
As a board member of Antietam Healthcare Foundation, the Health System's fundraising arm, Jack Hershey "wanted to get in and get started," said Sandy Pollack, the foundation's executive director.
The capital campaign is just starting, with a goal of $15 million to $18 million. As an early contributor, Pollack said, Hershey wanted to be a model for others.
Hershey agreed and said he'll talk about what he does only to generate momentum.
"When I (solicit) a contribution to my charity organization, I make mine first," he said.
Hershey said he and David Beachley each gave $250,000 to the Hagerstown YMCA, where an aquatic center bears their surnames.
Jack and Anna Hershey also are starting a scholarship program for Washington County Public Schools students. They are giving $20,000 a year for five years - a total of $100,000 - to help students who go to Lehigh University, which is his alma mater, and Cedar Crest College, which is hers.
"We're just trying to stimulate a little interest" in the colleges, Jack Hershey said.
Then, there was the time in 1992 when the Hersheys tried to quietly make a donation to United Way of Washington County, late in the annual campaign.
The couple pledged to match contributions up to $15,000, which they did. At first, they were anonymous, but their identities later were made known.
"I wanted them to reach their goal," Jack Hershey remembered this month.
The Person of the Year nomination letter sent by his son, John R. Hershey III, lists many of Jack Hershey's involvements and community causes, running onto a second page.
The YMCA, Hagerstown Rotary Club, Fountain Head Country Club, San Mar Children's Home, the Chamber of Commerce, Rose Hill Cemetery, Mason-Dixon Council of the Boy Scouts, the United Way, the Community Foundation of Washington County.
Hershey said he didn't have to worry about taking the first step into volunteerism. One organization will ask, then another, and word will get around that you're someone who will help.
"If you do a good job," he said, "they'll come after you. It gives you a certain amount of satisfaction."
Hershey received a bachelor's degree in business administration at Lehigh University. His first job was as an accountant for the DuPont Corp. in Wilmington, Del.
He remembers coming home to Hagerstown and seeing a local broker paint "a dazzling picture" of the industry. He joined.