When a customer arrived at Apple Discount Drugs years ago carrying an aging heating pad in a bedraggled box, complaining it wasn’t working, Len Winkleman didn’t hesitate to give her a new one.

That memory is one that remains dear to Jeff Sherr, who was Winkleman’s business partner at the Fruitland establishment, and who, as the 50th anniversary of the business approaches, took a little time to reminisce about that friendship and the mentor he cherishes.

“Len believed in taking care of the customer. He would say, ‘Even if we don’t get credit, it’s OK. It’s OK to lose the battle as long as you win the war,” said Sherr, who now owns Apple Drugs. Winkleman’s knack for being a humanitarian first, before making a profit, impressed Sherr.

“You know, you could look at the box that heating pad was in and see it was like 7 years old. The box was all dog eared. Our clerk, Patty, who had been with us 40 some years, she walked back into the office that day and she said, ‘This lady wants to return this or exchange it for another one.’ Len said, ‘Just give her another one.’ Len died in 2013 and what a loss it was. I was asked to speak at his funeral. I can sit around and tell Len stories all day. His way of teaching, there was always a story. We used to call him Aesop for Aesop’s fables. He used to do things I couldn’t believe.

“I’m 67 now. My parents were older when I was born. My parents had eighth-grade educations. They showed love but they didn’t prepare me as much for life. Len did. He was always there, even after he retired. He was still always there to come in and chew my butt out if he didn’t like the way I did something,” Sherr said with a laugh.

Winkleman opened the drug store on Oct. 11, 1971.

“The fact that we started out with such a small amount of square footage. The store was only 15 feet wide and 55 feet deep. That was the entire store. Len was a tremendous innovator. He was the beginning of discounting before discounting was really an issue. Some people around here hated him. We would sell insulin below cost. His philosophy was, ‘What difference does it make if you lose a nickel and or you make a nickel? Give them that comfort of service they aren’t going to get anywhere else.’ We have provided an incredible customer experience. Even though we lost prescriptions to stores like Walmart, to this day they always come back. That sweet taste of a couple dollar savings wasn’t worth the bad taste they got in their mouths from the bad customer service. People want that customer service. That’s what we are totally driven by to this day. Now my son is the person who is the operations person and I am trying to take more of a back seat,” he said.

Years ago, Apple Drugs was known as Ames Plaza Drugs. When Winkleman opened it, he had two business partners, Karl Wagner and Dick Schneider, Sherr said.

“Dick and Karl worked at Read’s Drug Store before Rite Aid. Both of those guys worked there. Dick knew Len from the New Jersey area and asked if he wanted to come down and open the store. It was 825 square feet. Today it is 20,000 square feet. This store has been pretty amazing. We are 50 years down,” he said, adding there are now 115 employees and more than 30,000 customers in the three Lower Shore counties.

Sherr’s wife, Joanne, joined the pharmacy in 1981 and their son, Zach, is Chief Operating Officer. Another son, Danny, works as a medical device representative for Johnson & Johnson and their daughter, Alyssa Sherr, is an occupational therapist in Raleigh.

There is also an Apple Drugs on Nanticoke Road, in the Pecan Square Shopping Center, in Salisbury. Another in Berlin opened in 2003 and closed in 2020.

“That store in Berlin had originally started as a medical equipment and oxygen store that was located in the Berlin Nursing Home. Palmer Gillis owned the medical center, and he asked if I was interested in putting a store there. The downfall was really support from the community as well as reimbursements that were coming from insurance companies. What we received in Worcester County was different from what we received in Wicomico County,” he said.

He also owns Snow Hill Pharmacy and finds the residents of the small town “just the nicest people.”

“I had people walk in when we were opening up down there. One man said, ‘Are you the owner?’ And he said, ‘You wait right here.’ He walked in with a bushel basket full of corn and cantaloupes to give me. He said, ‘We appreciate you being here.’ Just the nicest people,” said Sherr, whose employees think he’s pretty nice himself, since he makes an effort to talk to all of them every day and insists even new hires call him Jeff instead of Mr. Sherr.

“What drives me is passion. It has never been money. It has always been about passion and taking care of people. If you do those things the money will follow. You will make a profit, just the fact that you work hard. My philosophy has always been, ‘Do your best.’ Give it your best because you never know who’s watching. You can teach a job but you can’t teach caring about people. These are philosophies from Len. He had such an influence on me,” Sherr said.

Sherr first became involved with Apple Drugs in 1979. A pharmacist, he was working as a sales representative for Eli Lilly & Co., a pharmaceutical firm, and became friendly with Winkleman.

“He was very kind to me. He lost a pharmacist and I said to him, ‘I’d be glad to help you in the evenings or Saturdays because my wife is a pharmacist, too, and she is working in Cambridge. I’ll help you while she is over there,’” Sherr said. In 1982, Winkleman asked him to become his partner.

It didn’t take long for Sherr to find a soft spot in his heart for Eastern Shore residents after moving to the Shore.

“These people, they are real people, the salt of the earth,” he said, recalling his surprise and delight the first time he stood in line at a local grocery store and the customer in front of him turned around to chat.

“I grew up in Baltimore and I found this really is quality of life. This is good stuff,” he said.

In 1985, Winkleman was approached by a company about selling the drug store. After discussing it with Sherr, the men agreed to sell to Beverly Enterprises, who, at the time, was the largest nursing home provider in the country.

“We thought it would be a good opportunity to learn more, to have career opportunities for our employees. They painted a pretty picture but in 1987 Len decided to retire,” said Sherr, adding he took over. In 1989 Sherr contacted his former partner and said he wanted to buy the drug store back “because they had run it into the ground.”

“I asked him if he wanted to come back and in his very animated way said, ‘Yeah, man. That sounds cool. Let’s do it.’ So we created a new corporation. In 1991, Ames left town and the shopping center didn’t have a name. We looked for a name and we wanted it to start with an A because at that time people used the telephone book when they were looking for businesses. We wanted it to be easy to spell and health related. So we created Apple Discount Drugs. We created a happy apple that we still use as our trademark, a winking apple that we created in 1992,” he said.

Also that year, Winkleman and a junior partner decided to go into partnership with pharmacists on the Eastern Shore of Virginia and create an oxygen company that operated out of Apple Drugs. Advantage Medical stayed until 2017 and then closed due to insurance reimbursements, Sherr explained.

“I do indeed have sand in my shoes. I love my community. I use the word ‘love’ strongly. I love the community and I will do whatever we can do to help the community and to be part of the community .The community has to support the local businesses because it’s the local businesses that are supporting you.

“There are so many diabetics in the area and so many people don't know about the disease. We have committed ourselves to provide that service. It’s that extra step that really makes the difference, whether it’s medical equipment or oxygen or IVs. I don’ t believe your pharmacy should be the place you buy your cereal, your cosmetics. We are in health care. That is the vision I always had,” Sherr said.

“Sometimes I look at Len’s picture here on our wall and I think. ‘What would Len do?’ I’m blessed I found my angel. He took me under his wing. And we are going to continue for the next 50 years.”