September-October 2013 | GIVING NATURE

Reese Cropper, III, Insurance Management Group founderThe Insurance Management Group staff



Through his charitable efforts, and those of his staff, Reese Cropper, III is making a difference in the lives of people in our community

Written By: Jonathan Westman | Photographer: Grant L. Gursky

Community. Its definition refers to “people with common interests living together in a common area.” Here on the Eastern Shore, its meaning extends far deeper than the traditional surface connotation. Community in these parts refers to “people with common interests living together in a common area who unite in times of adversity or enthusiasm to 
assist one another for the greater good of all.” It doesn’t read that way in Webster’s, but it should.

Reese Cropper, III, founder of Insurance Management Group and a lifelong Berlin/Ocean City resident, embodies the Eastern Shore definition. His upbringing, love for this area and desire to make a difference in the lives of others have had 
a profound impact on our community. 

“When I was growing up, I watched the Ray Coates, Srs. of the world start Little League in Berlin,” Reese said. “I remember my father being in the Lions Club, and they would stock these great big grocery carts with food each Thanksgiving and give them to families in need. I remember people helping the less fortunate in the church. People were always helping one another, and those values were instilled in me at a young age.”

After graduating from Lynchburg College with a business degree in 1982, Cropper continued his studies at Dickinson College and obtained his insurance licensure. Upon returning to his roots, Reese began working for the insurance firm started by his grandfather in 1929. He also commenced his volunteer efforts by donating his time to worthy organizations that he felt were making an impact in both the personal and professional arenas, including founding the Berlin Chamber of Commerce.  

“When you’re younger, time is the valuable asset that you have the ability to give more readily,” Reese said. “Now that I’m a bit older, I have the financial wherewithal to be able to assist organizations and causes that I truly believe in.”

In 1994, the insurance agency partnership he worked for was sold and Reese began building his own client base, which is known today as Insurance Management Group, Inc. Cropper directs his philanthropic energies toward charities that 
fall into classes of categories he believes directly impact our local community. They are: education, children, sports and religion/history. Here’s a rundown of some of Reese’s favorite charities:
Diakonia:  “I support Diakonia partly because they lost a large portion of their government funding, but also because I’ve seen firsthand what they do for people in our community.” Among other contributions, Reese donates a golf tournament to Diakonia that serves as one of the organization’s largest annual fundraisers.
Worcester County Youth & Family: “Gosh, what a benefit they are to our community. They’ve helped so many people over the years and helped me personally in my life, and I will be forever grateful.”
St. Martin’s Church: “I strongly believe in preserving the rich history of our area. I also see what religion can do for people. I’m not a religious person, but when you see how religion helps people, I wish I had that in me.”
Berlin Little League:  “These little guys have done an amazing job. Sports instills so many wonderful life lessons. I had the team autograph my shirt, and rather than just giving the league a check, I purchased 
raffle tickets and gave them back to the kids to win the prizes. Our IMG employees went to the field to present them with our donation. It was a lot of fun.”

Coastal Hospice: “I’ve had a grandparent and friends who have needed hospice and it’s a tremendous asset to the patient and the family members left behind. They also want to build a hospice facility here in Berlin. I want to see that happen. I may end up as a patient in that building one day. It’s the right thing to do.” 
Worcester Preparatory / Stephen Decatur schools: “I strongly believe in education, and I also believe one of the biggest challenges of our generation is preparing kids for the future.”
Cropper, also a proud supporter of the Ocean City Art League, has served on the Tri-County Insurance Agents Board and has obtained a special designation of Community Insurance Risk Management Specialist, (CIRMS). Due to Reese’s 
expertise in condominium insurance, former Maryland Governor Robert Ehrlich appointed him to the Community Ownership Task Force. Today, Reese is still called on to testify before the state legislature in Annapolis or at the Maryland Insurance Commission regarding various insurance-related issues affecting condominium-related matters through-out the state. 

Presently Reese serves on the board of directors at Calvin B. Taylor Banking Co. and Worcester Preparatory School’s board of trustees. He’s also the chairman of the Ocean City Employee Pension Board, and he serves on the Maryland chapter of the Community Association Institute’s legislative action committee. Additionally, Reese chaired fundraising drives for March of Dimes and the American Cancer Society, among others. He’s also served as president of Berlin’s Taylor House 
Museum and, at the request of the mayor and city council, as Ocean City’s chairman of the Port Wardens. 

“I’m not alone when it comes to giving back to those in need. This community is the best at it,” Reese said. “When you see the Billy and Madlyn Carders and the Leighton Moores of this area, just to name a few, it’s a really special bond that this community shares. Whenever there’s a need, people always step up to the plate to help in any way that they can — more than we even know about.

“We’ve never aspired to be the largest insurance company in town,” Reese continued. “We strive to be very personable with our clients and genuinely care about their interests. That philosophy extends to our community efforts.” 

Reese relied heavily on his inveterate experience as a businessman and as a highly trained expert in risk assessment 
to inform his approach to philanthropy.

"Our business philosophy is to listen to clients while discussing the assets our client needs protected," offered Reese. “We discuss the levels of risk and measure that risk with the various options available to insure properties located in a coastal area such as Ocean City. The same is true in our giving philosophy: We look for ways we can help mitigate the risk an organization has so that their future plans and benefactors can grow and protect their assets and future.”

Cropper III’s giving nature permeates throughout his office. A large number of his employees give generously to 
organizations across the Shore, including: St. John Newman Church, Most Blessed Sacrament School, Stephen Decatur sports boosters, the Pop Warner scholarship fund, Coastal Hospice, Habitat for Humanity, and Hope and Outreach, to name just a few.

“Things have changed in this world, and I don’t mean for the better in a lot of respects,” Reese said. “I hope that what I do and what our team of employees does with our time and money helps in a small way to make our area better. That’s why we give from our hearts… to make a difference in someone’s life.”


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