Most families have a box of mementos and memorabilia from their parents, maybe their grandparents. Kirk Pinkerton CEO Bill Robertson’s box goes all the way back to the Civil War.

From inside, he pulls out a detailed archive of his family’s history of military and legal service, with personal diaries, letters and photographs that tell a five-generation saga beginning in Tennessee and ending in Sarasota, with detours to Gettysburg, France, Germany, Italy and beyond.

The earliest documents in Robertson’s collection are amongst the most fascinating. They include a personal, handwritten diary of the Civil War jotted down by Robertson’s great-great-grandfather, Col. John A. Fite, who fought for the Confederacy in the 7th Tennessee Infantry. He also recorded his thoughts in letters sent back home and in a memoir that is hundreds of pages long.

In his personal writings, Col. Fite tells the story of a young man who became a leader during the Civil War, meeting Robert E. Lee and drinking with Stonewall Jackson. Wounded twice, he led troops into battle during the Battle of Gettysburg, where he was captured as part of Pickett’s Charge. Held as a POW, he was imprisoned with thousands of other Confederate officers on Johnson’s Island in Ohio. Eventually released, he returned to his home in Lebanon, Tenn., and began practicing law, eventually becoming a judge.

Among Col. Fite’s belongings is a typed list in which he judges the effectiveness and bravery of his men. Most make the grade, while others are maligned: One soldier “deserted July 16, 1863; ought to have died when he was little.” Another “deserted to the enemy, May 20, 1864; should have died when he was little; afterwards shot by the Yankees.”

Col. Fite’s memoirs were typed up and then meticulously corrected with red ink, the paper stamped with the name of Col. Fite’s son, “N. G. Robertson, Lawyer, Lebanon, Tenn.” While N. G. did not service in the armed forces, he continued Col. Fite’s tradition of legal service, something he passed on to his son, John Fite Robertson, Bill’s grandfather.

John Fite Robertson made a record of his own military service, commanding an artillery battery as a first lieutenant in France during World War I, when he witnessed the world’s first aerial duels, “the greatest exhibit of flying skill I have ever seen,” and survived being strafed by German machine gun fire.

His memoirs are printed on legal paper bearing the logo of Robertson, Robertson, Walker, Cummins & Benson, the law firm he founded after relocating to Sarasota in 1925. John Fite Robertson later served as mayor of Sarasota. It was during his tenure, 1948-1951, that legendary City Manager Ken Thompson was hired; Thompson became the longest-serving city manager in American history and spent 38 years on the job.

Also included among John Fite Robertson’s paper are documents of tragedy. A generation after he shipped out to Europe, his two sons, John Fite Robertson, Jr., and William E. Robertson were sent to Europe to fight the Nazis. William fought with the 364th infantry and Gen. George S. Patton during the Battle of the Bulge, during which he was wounded, while his brother was killed leading troops into battle against the S.S. in Italy.

Among Bill Robertson’s collection is the original Western Union telegram sent to John Fite Robertson by Adjutant General James Alexander Ulio with news of the death of Robertson’s son’s. “The secretary of war asks that I assure you of his deep sympathy in the loss of your son First Lieutenant John Robertson Jr report received states he died July in Italy as result of wounds received in action letter follows,” reads Ulio’s telegram.

Some of John Fite Robertson, Jr.’s fellow soldiers reached out to his father to share stories of his bravery. Even after being mortally wounded, John Fite Robertson, Jr., continued to command and direct his men. “The men in his company showed in his last battle that they would follow him anywhere,” one of his fellow soldiers wrote. “I saw John that morning as he was being evacuated,” another soldier wrote. “Although badly wounded, he was cheerful and smiling, I don’t believe in much pain.”

Reflecting on his son’s life and death, John Fite Robertson wrote a brief biography with details of the young man’s upbringing and service. The book’s title,It Remains to Be Seen, references the last words his son said to him before shipping out. While saying goodbye, John Fite Robertson told his son he was a “great boy.” “That remains to be seen,” his son said, hugging and kissing his father in farewell.

John Fite Robertson, Jr., was posthumously awarded both a Bronze Star and a Purple Heart, and was eventually laid to rest in the family burial plot in Lebanon, Tenn. Among the Robertson family collection is a certificate signed by President Franklin D. Roosevelt, praising John Fite Robertson, Jr. “He lives — in a way that humbles the undertakings of most men,” reads the document.

While his son made the ultimate sacrifice for his country, in his writings, John Fite Robertson described the loss that all veterans feel after leaving combat behind. In the closing words of his autobiography he reflected on how his time in World War I had affected him. “I am aware of the fact that my service in France took something out of my make-up,” he wrote, “something that I, and possibly others, can’t understand, but in place of it I have memories and associations that no men can understand unless he too served Over There.”

“Growing up with my family’s history of service, I learned early on that all the freedoms we enjoy are due to the American soldiers protecting us around the globe,” Bill says. “As a fifth-generation attorney, I know that my rights, to say what I want without fear of retribution, to represent injured people and families who have lost loved ones and are trying to put their lives back together, to challenge the powerful, all depend on brave Americans standing up to safeguard the Constitution.”

Another lesson Robertson learned from his family history: what it means to take care of your fellow soldiers. After World War I, his grandfather helped found the American Legion, created to maintain the fierce relationships forged in European combat after hostilities were over. And his father would automatically provide pro bono help to any veteran in need, no questions asked.

Bill is doing his best to carry on both his family’s legacy of providing exceptional legal service and of helping veterans. On the last Friday of each month, he dedicates his WSRQ radio show, “Let’s Talk Law,” to Helping Our Heroes, created to assist veterans in need. Working with community partners like Goodwill Manasota and the Women’s Resource Center of Sarasota County, the show identifies a veteran in need each month, then tries to match him or her up with a local company looking to hire dedicated employees.

“We’ve been doing the program since March, and each month, the veteran we’ve featured has quickly landed a job,” Bill says. “But I know that’s just the tip of the iceberg. Often I’ve found that veterans simply aren’t aware of many of the resources out there to help them. And so we’ve launched a new website,, which will gather together every last resource we can find to help our region’s 130,000 veterans.”

On the site, veterans are able to find emotional and mental health support, find legal help and get assistance if they’re going through a foreclosure. Female veterans will find resources specifically tailored to their needs. It will also include information about job fairs and list employers who are looking to hire veterans, and share news about important programs like a Florida law that grants in-state college tuition to any veteran anywhere.

“Whenever I look through my family’s papers, I’m always astounded by how much they sacrificed to protect this country, and I’m so grateful to all the brave Americans out there now putting their lives on the line,” Bill says. “The least we can do is make sure we give them every opportunity to succeed when they return.”