“[The Yankees] will always be in my DNA, and I guess I’m in their DNA.” These were the words of Rollie Sheldon, who grew up as a Boston Red Sox fan and hated the New York Yankees. But Sheldon’s perspective changed after his professional baseball career started with the team he hated in 1960. Starting in the Bronx, with Mickey Mantle and Roger Maris as teammates, Sheldon became a part of the last phase of the Yankees’ dominant mid-century run. On August 31, the former Yankees pitcher passed away; he was 89 at the time.

“The Yankees mourn the passing of Rollie Sheldon and extend our deepest condolences to his family, friends, and loved ones,” wrote the New York Yankees on X.

Roland “Rollie” Frank Sheldon was born on December 17, 1936, to Frank and Elsie Sheldon in Putnam, Connecticut. From a humble background, Sheldon spent his summers on his grandfather’s farm, playing baseball with his cousins.

“My dad Frank was one of 14 children,” Sheldon recalled about his family. “He grew up on a farm and worked his tail off every day. It was a dairy farm, basically, but we raised a lot of vegetables, took in hay, and maintained a bunch of animals—cows, horses…I spent my summers up there on my grandfather’s farm and played ball with my cousins.”

Sheldon attended Woodstock Elementary School and then Woodstock Academy, where he established himself as a multi-sport player. He played basketball, soccer, track, and baseball, but he was only 5 feet 9 and never pitched for his high school team.

After his graduation in 1954, Sheldon and three of his classmates enlisted in the USAF. He was only seventeen and a half years old. Sheldon served in the US Air Force from June 1956 to September 1958 and was stationed at Spangdahlem Air Force Base in Germany. During his time in the Air Force, Sheldon played baseball in Germany and even threw a no-hitter.

“We played some great teams in Europe. In fact, we used to beat all the Army clubs over there,” Sheldon said, per the Society for American Baseball Research.

After Sheldon left the Air Force, First Lieutenant Shelby Metcalf invited him to Texas A&M to play basketball and help him with baseball. Sheldon attended with the help of the G.I. Bill, a US law passed in 1944 that helps military veterans pay for college, find jobs, and buy homes.

But he was homesick, and after a semester at Texas A&M, Sheldon transferred to the University of Connecticut. At UConn, Sheldon excelled in both basketball and baseball. In an NCAA tournament game, he was guarded by Basketball Hall of Famer Satch Sanders.

During his sophomore year, a 23-year-old Sheldon caught the attention of Yankees scout Henry Hesse. However, the scout thought he was 20 when, in fact, Sheldon was three years older. When Hesse said his parents would have to sign the contract since Sheldon was still a minor, the former player did not correct him. On June 4, 1960, Sheldon signed with the Yankees for a bonus estimated at $20,000.

“If he thought I was 20,” Sheldon reportedly said, “I wouldn’t say anything because I didn’t want to blow this opportunity to play pro ball…I believe anyone would have done the same thing…keep quiet.”

His decision to sign with the Yankees surprised his parents, but Sheldon did not want to miss the chance to go pro. He also clarified that all his official records had his real age. He may not have cleared Hesse’s misconception, but Sheldon was not involved in age fraud. Once the contract was signed, it marked the beginning of a new phase in Sheldon’s life.

Rollie Sheldon’s baseball journey

In 1960, Sheldon began his pro career with Auburn in the Class-D New York-Penn League. He impressed everyone with a brilliant 15-1 record, posting a 2.88 ERA. Manager Bob Bauer called him “one of the best-looking pitchers I have ever seen in Class D ball.” Sheldon climbed the ranks quickly from there.

A year later, Sheldon joined the advanced camp for top prospects, and the Yankees selected him following Spring Training, where he impressed manager Ralph Houk. Sheldon also won the James P. Dawson Award as the outstanding rookie in camp.

Sheldon debuted for the Yankees on April 23 in Baltimore as a reliever and threw two scoreless innings. On April 30, he started his first game against the Washington Senators (now Nationals) in the second game of a doubleheader. He allowed only 2 runs in 7 innings, but took the loss as the Yankees scored only one run in the game. Sheldon recorded his first win on May 31, 1961, against the Boston Red Sox, his childhood favorite team. But Sheldon had one regret. He did not get the chance to pitch to his childhood hero, Ted Williams. The Red Sox star had retired the year before.

“I missed him by one year [Williams retired after the 1960 season]. I keep telling people I don’t care if he hit a gigantic home run off me. I just wanted to face him one time,” Sheldon had said.

Sheldon ended the 1961 season with an 11-5 record and a 3.60 ERA in 35 outings. He made the Yankees’ World Series-winning team but did not get a chance to pitch. The Yankees beat Cincinnati 4-1 in the Fall Classic.

Sheldon had a rough season in 1962 (5.49 ERA). He also discovered that he was tipping pitches, and though a changed pitching style helped, his troubles did not disappear. Sheldon was demoted to Triple-A in 1963, which he called “a shock.”

Sheldon was back again with the Yankees in 1964, after showing considerable improvement in Triple-A. In the same year, the Yankees made it to the World Series again. This time, Sheldon got a chance to throw. In Game 1 against the St. Louis Cardinals, Sheldon pitched in relief in the bottom of the eighth. The Cardinals were already leading 6-5 and scored two more runs off him, and ultimately won the game and, eventually, the World Series.

After the 1964 season, Sheldon resumed his studies and received his college degree. He also taught physical education at a school. But then the Yankees called him up in 1965, and Sheldon was back in the Bronx. However, the Yankees were missing a catcher with Elston Howard injured, and packaged Sheldon for a trade. The Yankees sent him to the Kansas City Athletics for Doc Edwards.

Sheldon enjoyed a regular role with the Athletics, posting a 3.95 ERA and a 10-8 record across 32 outings before being traded to the Boston Red Sox during the 1966 trade deadline in a six-player deal. Although he finally joined the team he had wanted to play for as a child, he struggled in Boston, going 1-6 with a 4.97 ERA. The Red Sox sent him to the Cincinnati Reds in December, but his major league career was over, and he spent the final four years of his career in Triple-A.

“It was the tail end of my career, and I was just trying to hang on. I had a little arm trouble here and there. I was just trying to extend my career as much as I could,” Sheldon said.

Sheldon’s baseball career ended in 1970, after which he settled in Lee’s Summit. After retiring, he started an insurance business. Sheldon had married Wanda McConnell back in 1962, when he was still at UConn. They have two daughters, Ronda and Lori. But the couple divorced after 18 long years of marriage in the 1980s. Sheldon later remarried and is survived by his wife, Shirley, two daughters, and two granddaughters.

Though Sheldon’s career was short-lived, he will live on in the memories of fans who grew up watching 1960s baseball.