IIAV Past President - Cruger S. Ragland, Jr.

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This is the 31st in our series of conversations with former leaders of Independent Insurance Agents of Virginia. Cruger Ragland served as IIAV Chairman of the Board after being elected in 2009 at the convention in Williamsburg.

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The sprawling metro Dallas, Texas area has a general population of 6,778, 524. Kilmarnock, Va., on the other hand boasts a count of living, breathing human beings of just over 1,255. What would drive Cruger S. Ragland, Jr. from one to the other?

Born in Dallas in 1954, Ragland grew up in an insurance family. Not only was Ragland’s father an insurance agent, but there is a host of close kinship in this industry. Originally running a successful real estate firm in Dallas, Ragland’s father was suddenly and unexpectedly thrust into the insurance agency business. Ragland’s great grandfather, Cruger T. Smith, was a partner in the Craddock and Smith Insurance Agency. Smith’s son-in-law, Alphonso "Fonse" Ragland, Jr. was Cruger’s grandfather and he left that agency and founded Ragland Insurance Agency in 1943. Cruger’s father, a University of Texas graduate, joined the agency in 1954. An automobile accident claimed the life of Cruger’s grandfather, "Fonse," in 1958 and Cruger’s father ran the agency alone for twenty years until Cruger’s brother Scott joined the firm in 1978.

In addition to the family members on Cruger’s father’s side of the family who were in the insurance business, his mother’s stepfather was a Vice President with Gulf Insurance Company out of Kansas City (now part of Travelers).

Before graduating from Highland Park High School in Dallas, Cruger had spent some time at Camp Deerwoode in Brevard County, N.C. not far from Asheville. Dallas is a fine city, but the beauty and hilly countryside of western North Carolina is grand. Cruger’s love of the mid-Atlantic region caused him to look at colleges in the area. He settled on Hampden-Sydney College. Growing up in Dallas, Cruger was an avid sports enthusiast favoring football, soccer and golf. He was looking for a small-town atmosphere and one cannot find a much more "small-town" atmosphere than at Hampden-Sydney. Highland Park High School has a student population of 1,950. When Cruger attended Hampden-Sydney College, there were about 690 male students. "My mother attended Sweet Briar College in Amherst and actually quite a few Dallas area guys went to Washington and Lee," says Ragland. He adds, "So H-SC was not as dramatic a move as one would suspect."

Throughout his college career, Ragland was quite certain he’d one day return to Dallas and enter the agency ranks. However, Cruger met Mary Rosenberger from Waynesboro and his sphere of influence changed. Mary, who attended Longwood College in nearby Farmville, Virginia, and Cruger began dating seriously. Upon graduating from H-SC in 1976 with a degree in Religion, Ragland began working with Reliance Insurance Company as a Casualty Underwriter in Maryland. He and Mary married in August of the following year, and Reliance transferred Ragland to Richmond as a Field Representative. In this position Ragland was introduced to many agents and agencies and in 1979 Irwin Clark with Hubbard Insurance Agency, Inc. in Kilmarnock brought Cruger in as a producer.

Hubbard Insurance Agency, Inc. is prominently positioned on the main thoroughfare of "downtown" Kilmarnock. It was established in 1950. Much like most smaller communities throughout Virginia, Cruger recalls that, "In 1979, Kilmarnock was a close-knit, rural venue and, frankly, I was not immediately and fully accepted." But Cruger and Mary absolutely fell in love with the area. Whatever "lure" to return to Dallas existed was overridden by the atmosphere of Kilmarnock.

When working with Reliance Insurance Company in Richmond, Ragland was a member of the Independent Insurance Agents of Virginia. Upon entering the agency ranks, Tommy Via from Blacksburg encouraged him to become more involved in the Association and Ragland recalls a Young Agents Conference in Fredericksburg that brought him even closer to other agents and inspired him to become more engaged in Association leadership.

Ragland readily admits that he became quite disturbed by a stance the Association took on a bank-related issue many years ago and he "drifted away from Association activities for awhile." Eleven years ago, Ragland again began working on technical insurance issues through IIAV at the committee level among such notables as Steve Harris (IIAV Past President 2004-2005); Tom Phillips with TB&R; David Priest, (IIAV Past President 1994-1995); and Chuck Cralle (IIAV Past President 1997-1998). A couple of years later, IIAV Executive Bob Bradshaw asked Ragland to consider serving on the IIAV Board of Directors.

Cruger Ragland rose in leadership positions at IIAV and was elected Chairman of the Board at the Williamsburg Convention in 2009. Ragland’s father had been the Chairman of the Board of the Independent Insurance Agents of Texas. What a strong family insurance heritage and legacy!

During his term as Association Chairman, Ragland successfully wrestled with the challenges of ensuring the fiscal integrity of the Association as it faced the economic downturn. Additionally, growing the IIAV Building Fund was one of Ragland’s priorities. He and Bob Bradshaw flew to Providence. R.I. and secured a generous $10,000 contribution from MetLife Auto & Home for the Building Fund. Ragland has served on the carrier’s national council for several years.

"I’ve thoroughly enjoyed the experience in this industry," exclaims Ragland, "and it is important to me to give back to an industry that has been good to me."

As Secretary/Treasurer of Hubbard Insurance Agency, Inc., Cruger is focused on the direction of his agency. He encourages staff education and association participation.

When Ragland started with the agency 32 years ago, the business mix was 30 percent personal lines and 70 perecent commercial lines. Today, the volume is exactly opposite. In 1979, the agency was a heavy writer of oyster and crab houses along the Chesapeake Bay and its many local tributaries. This intentional devotion to growing the personal lines element of the agency has resulted in steady growth and a much more stable book of business. Of course, being so close to the Bay offers some growing underwriting challenges and this will continue to be an area of the business requiring a watchful eye.

Another reason for the continued success of Hubbard Insurance Agency, Inc. has been the consistency and loyalty of its staff. When Cruger joined the agency in 1979, three (since retired) staffers had over 40 years experience EACH. The support staff in the agency today, Shannon, Christy and Carol, has a average of 17 years experience.

Ragland professes, "We don’t seek to be all things (insurance) to everyone." He adds, "Do what you do well and right and the business will stay with you."

Setting Hubbard Insurance Agency apart from others is the agency’s commitment to service. By way of example, during the devastation of Hurricane Isabel, Ragland met with every client who’d suffered physical damage. Even without power to the agency, Ragland accompanied the CAT adjuster to dozens of homes. Service to his clients also means using prudently the claims draft authority from his insurance carriers.

Ragland’s presence in the community is strong. He’s been involved with the Lancaster County Parks & Recreation department and he was instrumental in forming the local YMCA. When Ragland’s two sons, Will and Alex, were younger, Ragland participated in Little League Baseball, coached JV baseball at the local high school for three years, and served as Assistant Coach for the varsity team one year. Church involvement has always been a part of his family life, too.

Mary opened a unique retail shop in nearby Irvington called Bay Window 25 years ago.

Cruger and Mary reside on the banks of the Corrotoman River. The kids are now grown (28 and 30), so Cruger has more time for one of his passions: golf. As a member of both the Tartan and King Carter courses, Ragland’s 5 handicap comes in handy during tournament play. He also admits — when pressed — to possessing not one, but two holes-in-one, also known as the holy grail of golf. One of these accomplishments occurring during a CPCU outing.

According to Ragland, "This is still a great business. It requires hard work and honesty, but the rewards are generous." "More important," Ragland explains, "is to be doing something you really enjoy. It makes it all so worthwhile."

To illustrate this point, Ragland cites one of his largest accounts. Thirty-two years ago a young worker at a Safeway grocery store was moonlighting as a landscaper. He had just purchased his second pickup truck. One day one of his vehicles was in an incident, colliding with the other. His agent at the time had only physical damage on the vehicles. Ragland picked up this small account. This now six-figure account has been with Ragland ever since.

From big city Dallas to small town Kilmarnock — it is not the path Cruger Ragland originally envisioned. But it is the path of his choosing and one Cruger and Mary have relished. Stroll through Lancaster County, Va. today and witness the friendly attention Cruger now draws. A far cry from the days in 1979 when the "outsider" made his way into Kilmarnock. Hard work. Honesty. Integrity. Service. This is real path of Cruger Ragland.


If you missed the previous articles you will find them on our website at www.iiav.com under News.

Danny Mitchell (dmitchell@iiav.com), IIAV Membership/Marketing Director