Richard (Dick) D. Winters was born on January 21, 1918, in Lancaster, Pennsylvania. He resided with this parents Richard and Edith Winters in Ephrata, Pennsylvania. He spent his time playing in the farm fields and stockyards. When he was thirteen, his family moved to Lancaster, Pennsylvania. It was at this time that Winters's younger sister, Ann, was born. Winters attended Franklin and Marshall College because it was located a short distance from his house. He spent the entire summer before starting college doing odd jobs to raise the money he needed to go to school.

During college, he was a member of the Delta Sigma Phi fraternity. In 1941, he graduated with a Bachelor of Science in Economics. Winters enlisted in the United States Army on August 8, 1941. At this time, he had hoped to shorten his time in service. He was hoping to avoid a full term of service due to the draft. By enlisting on his own, Winters planned on serving a one year tour instead of three. During basic training he often wrote home to a local girl named Annid DeEtta Almon. Winters dated DeEtta for several years, and she became his closest confidant. After basic training, Winters was selected to attend the Army Officer Candidate School (OCS) located in Fort Benning, Georgia. At this school, Winters met and befriended Lewis Nixon, who became a longtime friend and war compatriot.

After OCS, Winters was assigned to the 101st Airborne Division as a Second Lieutenant. He volunteered for paratrooper training and was assigned to Company "E" (Easy Company) of the 2nd Battalion, 506th Parachute Infantry Regiment. While at paratrooper training, he received a promotion to First lieutenant and a new job as Executive Officer. In September 1943, the 101st Airborne Division was deployed to England in preparation for the Normandy invasion. During the invasion, the aircraft carrying the entire headquarters element of Easy Company was shot down by German anti-aircraft. Winters became the defacto Commanding Officer of Company E. During this invasion, Winters led thirteen of his men in destroying a Battery of German 105mm Howitzers, which were manned by a full platoon of Germans. He also obtained a detailed map of all German defenses along the Utah Beach. This assault became known as the Brecorut Manor Assault. For his actions, Winters was recommended for the Medal of Honor, but he was awarded the Distinguished Service Cross instead.

Winters again showed renowned heroism in September 1944 when he successfully led twenty of his men in attacking a German force of 200 soldiers. In Winter 1944, Captain Winters and his men occupied the Bastogne area, which was the brunt of the Battle of the Bulge. Winter and his men held their place until U.S. Third Army was able to break through the enemy lines. Shortly after, Winters received his promotion to Major, a rank he held for the rest of his military career. In November 1945, Major Winters returned home. Upon his return home, Winters worked for Lewis Nixon at Nixon Nitration Works. While working in New Jersey he met Ethel Estoppey. After several dates, they married on May 16, 1948.

In 1951, Major Winters was reactivated by the U.S. Army, leaving behind his wife and a one year old son. This time Winters was stationed in Fort Dix, New Jersey, training infantry and Army Rangers units. He served three years in this position before leaving the Army for the last time. He returned to New Jersey, but found that his position at Nixon Nitration Works filled. Winters worked some dead end jobs before founding R.D. Winters Inc. His company specialized in selling livestock feed to farmers in Pennsylvania. Shortly after starting up his company, Winters and his family moved to Hershey, Pennsylvania. He eventually retired at this farm house.

In Autumn 1988, the 101st Airborne had a reunion meeting in New Orleans, and historian Stephen Ambrose was looking for his next story. Ambrose wanted to tell the story of D-Day. At the reunion, Winters sat back and listened to others boast about their stories. After returning home and reviewing his wartime notes, Winters decided to take action. On February 26, 1990, Winters met with Ambrose and started to tell the tale that became Band of Brothers. The book, arguably one of Ambrose's greatest works, was published in 1992.

Six years later, Winters was informed that Tom Hanks was interested in purchasing Band of Brothers with the intent of turning it into an HBO miniseries. Principal filming began in April 2000 under the guidance of Tom Hanks and Steven Spielberg. The first episode aired on September 9, 2001. This show launched Winters into the spotlight. For the next two years he kept busy with public interviews and speeches. His wife, Ethel, managed his publicity. In 2006, he published his memoirs, Beyond Band of Brothers. Winters died on January 2, 2011, in Campbelltown, Pennsylvania.