[4][3]: 6 At Franklin and Marshall, Winters was a member of the Upsilon chapter of Delta Sigma Phi fraternity and participated in intramural football and basketball.

Winters wrote in his memoirs that he "felt a strong sense of duty," but "had no desire to get into the war" and chose to let himself be drafted after graduating college instead of living with the uncertainty of being called up at an unknown future date, which might have "interrupt[ed] a promising business career," and to fulfill the one-year requirement of service for draftees rather than the three-year term for Regular volunteers.

[3]: 7  While the rest of his fellow trainees were deployed to units stationed in the Panama Canal Zone in early December, Winters remained at Camp Croft to help train draftees and other volunteers.

In April 1942, four months after the United States entered World War II, he was selected to attend Officer Candidate School (OCS) at Fort Benning, Georgia.

[7]: 18 [3]: 18 On June 10, 1943, after more tactical training at Camp Mackall, North Carolina, the 506th PIR was attached to Major General William Lee's 101st "Screaming Eagles" Airborne Division.

[7]: 52 In the wake of this incident, several of the company's non-commissioned officers (NCOs) delivered an ultimatum to the regimental commander, Colonel Sink, threatening to surrender their stripes unless Sobel was replaced.

Nevertheless, he realized that something had to be done and decided[7]: 54  to transfer Sobel out of Easy Company, giving him command of a new parachute training school at Chilton Foliat.

[3]: 80  Losing his weapon during the drop, he nevertheless oriented himself, assembled several paratroopers, including members of the 82nd Airborne Division, and proceeded toward the unit's assigned objective near Sainte-Marie-du-Mont.

[7]: 76  With Meehan's fate unknown, Winters became the de facto commanding officer (CO) of Easy Company, which he remained for the duration of the Normandy campaign.

[7]: 92 Later that day, Winters led the Brécourt Manor Assault which successfully destroyed a battery of German 105mm howitzers,[8] which were firing onto the causeways that served as the principal exits from Utah Beach.

[7]: 78–84  The Americans estimated that the guns, which were south of the village of Le Grand-Chemin, were defended by about a platoon of 50 German troops, while Winters had 13 men.

[3]: 112  The citation for his DSC reads as follows: The President of the United States of America, authorized by Act of Congress, July 9, 1918, takes pleasure in presenting the Distinguished Service Cross to First Lieutenant (Infantry) Richard D. Winters (ASN: 0-1286582), United States Army, for extraordinary heroism in connection with military operations against an armed enemy while serving with Company E, 2d Battalion, 506th Parachute Infantry Regiment, 101st Airborne Division, in action against enemy forces on 6 June 1944, in France.

First Lieutenant Winters with seven enlisted men, advanced through intense enemy automatic weapons fire, putting out of action two guns of the battery of four 88-mm.

[3]: 136–137  Returning to headquarters, they reported that they had encountered a large group of Germans at a crossroads about 1,300 yards (1,200 m) to the east of the company command post.

[3]: 137  Realizing the seriousness of the situation, Winters took one squad from 1st Platoon, and moved off toward the crossroads, where they observed a German machine gun firing to the south, toward the battalion headquarters, from a long distance.

[3]: 200  Shortly afterwards, Robert Strayer, now a lieutenant colonel, was elevated to the regimental staff and Winters took over as acting commander of the 2nd Battalion.

[3]: 255 Winters was recommended for the Medal of Honor for his leadership at Brécourt Manor, but instead received the U.S. Army's second-highest award for combat valor, the Distinguished Service Cross.

[7]: 306  On May 16, 1948, Winters married Ethel Estoppey[4][3]: 256  and continued to pursue his education through the GI Bill, attending a number of business and personnel management courses at Rutgers University.

[3]: 256  He was ordered to join the 11th Airborne Division at Fort Campbell, Kentucky, but he was given six months to report and in this time he traveled to Washington, D.C., to speak to General Anthony McAuliffe, in the hope that he could convince the Army not to send him to Korea.

[3]: 257 While at Fort Dix, Winters became disillusioned with his job, finding that he had little enthusiasm for training officers who lacked discipline and did not attend their scheduled classes.

[4] Winters also attended the 54th Primetime Emmy Awards on September 22, 2002 at the Shrine Auditorium in Los Angeles when the Band of Brothers miniseries was nominated in multiple categories.

[3]: 289  During an interview for Band of Brothers that was both the miniseries' final scene and included in the official HBO companion documentary We Stand Alone Together, Winters quoted a passage from a letter he received from Sergeant Myron "Mike" Ranney: "I cherish the memories of a question my grandson asked me the other day when he said, 'Grandpa, were you a hero in the war?'

[17] Winters agreed for the statue to bear his resemblance on the condition that the monument would be dedicated to all junior officers who served and died during the Normandy landings.

[18] Among the attendees were World War II veterans, former Pennsylvania governor and first Secretary of Homeland Security Tom Ridge and Maj. Gen. Jim McConville, the 101st Airborne's commanding officer.

[19] During celebrations of the 70th anniversary of the landings in 2014, a party including Lewis, fellow Band of Brothers cast members Ross McCall (Technician 5th Grade Joseph Liebgott) and James Madio (Technician 4th Grade Frank Perconte) and Private 1st Class Jim "Pee Wee" Martin of G Company, 3rd Battalion of the 506th Parachute Infantry Regiment laid a wreath there.

[20] A cast of the sculpture was placed in Ephrata, Pennsylvania, in a plaza on the Ephrata-to-Warwick linear trail park near Railroad Avenue and East Fulton Street, where Winters lived with his family from ages two to eight.