Reaching the Summit: The Legend of the Doggedly Successful, Remarkably Interesting Doc Dockery

By RJ Walters
Photos by Paul Bostrom

Editors note: This story was originally published in June 2022. Doc passed  away peacefully at the age of 89  on Aug. 1, 2022. 

On the benches where many a sunrise and sunset have been marveled at along the Lake Hollingsworth Loop, conversations abound.

If people could tune into a frequency that listened in on those conversations they would hear, amongst other things: reflections on the past and hopes for the future; exchanges about elected officials and with elected officials; stories about events that took place just blocks away as well as experiences on other continents; painful beginnings, successful endings and everything in between; lively debates from Republicans, Democrats and Independents; words about those who served in wars past and what might cause conflicts to come; and good ole’ boys and established businessmen alike just trying to make sense of the human experience.

The truth is if a passerby heard stories like that on the shores of Lake Hollingsworth, they all very well could have been told by the same man – the doggedly successful, remarkably interesting 89-year-old Doc Dockery.

For more than six decades he has been strolling around the lake, talking to locals he calls “bench buddies,” and for just as long he has been making an indelible impact on Lakeland and around the world.

First, a Moccasin

Standing in front of the newly completed eight-story Summit Consulting building along the Lake Mirror skyline in downtown Lakeland, Dockery admires a structure that is not his, but would likely not be standing there without him.

The CliffNotes version of that story reads: self-made businessman sells growing workers compensation business he started in Lakeland for millions in the mid-1980s, and nearly 40 years later the thriving company employs more than 700 workers across 14 states and has the largest market share of any workers’ compensation company in Florida.

The long-form of that story is built on so many interwoven stories that Dockery actually published an autobiography titled “Country Boy” in 2011. (you can access a free digital version of it at It is a self-directed version of his journey from the foothills of the Blue Ridge Mountains in North Carolina, where he was born and his dad abandoned the family when Doc was 8, through an admirable career in the military all the way to prominence that included friendships with several Presidents and visits to nearly every corner of the globe.

But the peculiar part to him is that the scenes of his life revolve heavily around the people, places and inspirations of a city that he once said “would probably not have been his choice if he had been looking for a place to call home forever.”

At 26 years old, Dockery had completed an 8-year stint serving in the Air Force, and was ready to start a career, but he needed to finish his degree. He applied to the University of Miami, the University of Florida and Florida Southern College. He decided he would enroll in whichever school would transfer over the most credit hours from his previous university work.

“By one credit hour, Florida Southern won out over the others,” Dockery says. “That’s how I got here.”


Country Grit, City Hustle

One could spend days reading about how Dockery ascended from a part-time writer who lived on a daily food budget of 25 cents to an executive in the Florida Roofing and Sheet Metal Contractors’ Association to an entrepreneur who opened Summit Consulting, Inc., and became a millionaire by selling it less than a decade later.

One also doesn’t have to search hard to learn plenty about his very public marriage to decorated Florida Senator Paula Dockery – who campaigned for the governor’s seat for a short time in 2010 – who he has been happily married to for 32 years.

But what is equally as interesting about this Lakeland legend is the people he has met, the people he has impacted for and what he attributes his success to.

“Loving and learning how to interact with other people,” he says, is one of the keystones to his many accomplishments. “People that I brought in to help me have been responsible for my success.”

His propensity for hiring employees with a strong drive and purpose stems from his own experiences. When asked about how he became willing to take risks, Dockery says it began out of necessity. After his dad left the family, his mom fell ill and was bedridden. One day, she called Crafford (his middle name) to her bedside, and asked him to step up.

“She said…you’ve got to cook something for us. And I say ‘Okay, mom, what will I cook?’ We had potatoes and that’s the only thing – so I cooked potatoes.

“I said, ‘Mom, how do I cook?’ and she said, ‘Well we have a stove in the kitchen.’ So I guess the first risk I took was lighting a kerosene stove at 8 years old.”

In one of his first business ventures he played it safe and hired a guy who fit the bill on paper, but he quickly realized lacked the necessary intangibles. He fired him, and soon after hired a man with no experience who he could tell was teachable and driven. The partnership was profitable for both.

At Summit, one of his many valuable employees over the years started in an entry level role, but she strived to grow along with the company. Summit helped put her through school to earn her accounting degree at Florida Southern, and soon after she came back to Doc and shared her desire to earn a Master’s.

Eventually she earned her Doctorate and ended up being an accounting professor at a college. She epitomized three traits that Doc said guided his hiring mentality over the years: ambitious, hard working and unafraid to fail.

A Political Waltz

As he excelled as a businessman, Dockery also found his voice as a public servant.

In his younger years, Dockery was a registered Democrat, but by 1970, when he ran for a spot on the Polk County School Board, he was a Republican.

His transition to Republican began when he took a liking to gubernatorial candidate Claude Kirk. Dockery’s first official campaign contribution was a small wad of cash he donated to Kirk’s campaign at an event at the Lakeland Holiday Inn. That was just the beginning, and as one Tampa Bay Times article puts it, “Dockery emerged as one of the pioneers who helped build the Florida GOP into a dominant force.”

“…back then being a Democrat, hell, it was the thing to do, and there weren’t any Republicans,” he says.

That’s part of the reason he ran for the School Board — to put a face with the local Republican movement — and to his complete surprise, he won that race.

He parlayed his influence, business acumen and relational currency into a seat at many tables over the years.

One issue he spent an abundance of time, energy and personal finances on was bringing a high-speed rail system to Florida that would span the length of the East Coast. Floridians today know that such a system is still not complete, but Dockery made significant in-roads that led to a lot of the high-speed rail infrastructure that is now in place.

In 1988, Florida Gov. Bob Martinez appointed Dockery to the Florida High Speed Rail Commission. Dockery’s commitment to a rail system that would rival the bullet trains of Asia and the connectional framework of systems in Europe was so great he spent nearly $3 million of his own money to help get an amendment passed to the state constitution in 2000 that required the construction of a high-speed rail system that connected at least five major urban centers. Four years later, voters repealed the amendment.

Today, Dockery notes the success of the Brightline system in Miami, Ft. Lauderdale and West Palm Beach, but also admits he learned a long time ago that making progress in politics is a lot like learning to dance.

“It wasn’t an engineering thing, but it was political,” he said. “It was and still is and always will be.”

No Regrets

In his office, Dockery sits across from an expansive map of the world. The countries he has visited are yellow, while the rest of them are green. One could argue that Dockery has seen more of the world than he has not.

Where is one place he would like to visit if he could hop on a plane today and have an itinerary set tomorrow? Greenland.

“It was difficult to go the last time I checked because you had to fly into Denmark to then get to Greenland, but I expect it’s easier now,” he says.

Ask Dockery if he has any regrets though, and you’ll have to be comfortable with a long pause as he tracks back through a colorful, purposeful life.

“I don’t have any real regrets in my life. I don’t,” he says looking off into the distance. “I’m sitting here thinking…I’ve had some, but they are just small and you make changes to adjust.”

Dockery said until recently he was somewhat uncomfortable with the idea of “his legacy” but some of his colleagues have helped put it in perspective for him, either through conversations like the ones he’s enjoyed over the years around Lake Hollingsworth or through letters like one he received in the mail recently from former Florida Senator Rick Dantzler.

The note included the statement: If you were younger, you’d leave both parties and build the Independent party into a force because you were a builder.

“You see, a note like that…still I’ll get them,” Dockery says. “How could a person want a better legacy?”