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Baseball: Southold fixture has baseball in his blood

April 27, 1955
To: Thomas O’Brien
Connecticut State Teacher’s College, New Britain, Connecticut
Subject: Scholarship

Mr. O’Brien,
Because of failure of yourself and the New York Yankees to make known the scholarship agreement entered into February 16, 1950 your contract with the Binghamton baseball club has been canceled by this office and you are now a free agent and can sign with any club except the New York Yankees.
—Ford Frick, Commissioner of Major League Baseball

Thomas “Tuck” O’Brien was born during the Great Depression into an Irish-American family in Fall River, Mass.

His father, Francis, a gifted athlete, was a draftsman for Con Edison. O’Brien’s mother, Winifred, when not tending to her five children, worked as a nurse.

Growing up in Cambria Heights, Queens, O’Brien always had someone to play ball with; whether playing a pickup game on the playground or in organized leagues. Attending Andrew Jackson High School in St. Albans, O’Brien played all four of his high school years on the varsity squad as a catcher and outfielder.

During the summer of 1948, O’Brien attended a baseball camp in Massachusetts run by the former Yankee pitcher Lefty Gomez and was awarded a trophy for being the most outstanding player at the camp. This drew the interest of the Yankees. When the Yankees were on the road, select players were able to work out at Yankee Stadium, something O’Brien did on many occasions. Recalling his Stadium highlights, O’Brien said, “One day when I was in the batting cage, Joe DiMaggio and his son were watching me.” O’Brien remembers DiMaggio’s son telling the Yankee great, “He hits just like you, Dad.”

O’Brien, who has lived in Southold for more than 60 of his 86 years, said, “I remember the day my father was watching and I hit a 295-foot homer into the rightfield seats.”

The Yankees had been courting O’Brien and had hoped to eventually sign him to a contract, as were the Pittsburgh Pirates. “There was a scout from the Yankees who would come over to our house on Friday nights and watch boxing with my father,” said O’Brien.

O’Brien had hoped to attend George Washington University on a baseball scholarship, but his grades were just below the standard for admission. The Yankee scout had a connection at Connecticut State Teachers College in New Britain, and the Yankees offered to pay O’Brien’s tuition. Assuming everything was on the up and up, and with the encouragement of his parents, O’Brien accepted the offer.

Midway through his college studies, O’Brien was drafted into the Army and served for almost two years as a recreational NCO. His job: play baseball. He also wrote a weekly newsletter for the troops, letting them know what was going on in the world of sports.

Taking a short leave from the Army, O’Brien married Cathy Chessa, who he had met at college. “Cathy was the only girl I ever dated,” he said. “I was very shy then.”

After a brief honeymoon, Cathy returned to college and O’Brien returned to his barracks.

Following his discharge from the service in the spring of 1955, O’Brien returned home and reported to spring training in Binghamton after receiving a signing bonus of $1,250. Branch Rickey of the Pirates had learned of the “scholarship” O’Brien had received from the Yankees and blew the whistle. A thorough investigation followed with MLB commissioner Ford Frick ruling in favor of the Pirates. O’Brien was notified by a telegram from Frick that his contract with the Yankees was canceled, allowing him to become a free agent and sign with any team, except for the Yankees.

The Pirates were still interested in his services along with the Chicago Cubs, Chicago White Sox and Detroit Tigers. O’Brien chose to sign with the Tigers and received a $3,000 signing bonus.

For the next three seasons O’Brien played for a number of minor league teams. The Witchita Falls Record News reported on April 13, 1957: “Tom O’Brien a scholarly baseball player is ticketed for duty this season with the Witchita Falls Spudders and is starting his third season in organized baseball and is looking forward to his first full-time baseball campaign.”

O’Brien had continued to pursue his degree in elementary education between the baseball seasons and graduated in January, 1957. Realizing that his age was working against a future in baseball, he began applying for teaching positions. He had heard about a semi-pro baseball team on Long Island in Riverhead that had lights on the field. He applied to the Riverhead School District where he was hired and taught for the next two years.

O’Brien scouted for the Tigers for a few years and had been told about some kid named Yastrzemski, but never got around to seeing him. “I blew that one,” O’Brien admitted.

O’Brien had also been doing some umpiring with Southold legend Dick Osmer. Osmer told him that an elementary school position would soon be opening up in Southold and that they also needed a baseball coach. He was hired by Southold and spent the next 35 years as an elementary school science teacher.

In the early 1970s, O’Brien was instrumental in developing the St. Patrick’s CYO basketball program and the North Fork American Legion Baseball League. “He knew the game of baseball and got the most out of you,” said Rich Mullen, a former player for O’Brien. “As a player you loved playing for him.”

O’Brien and his wife raised five boys, all exceptional athletes. “As parents our goal was to teach our boys to work hard and to get them through college so they could get a good job,” he said.

O’Brien has stayed busy in “retirement,” continuing to work in different capacities for Southold’s school system, and to date has spent 58 years working for the district. The spry octogenarian also mows lawns (push mower), and with his five children, 13 grandchildren, and one great-grandchild, he has much to keep tabs on.

How did O’Brien get the nickname “Tuck”? With a big smile he said, “When I was little I liked the nursery rhyme, ‘Little Tommy Tucker Sang For His Supper.’ ”

Asked what three words best describe him, a contemplative O’Brien replied, “Lucky, industrious, happy.”

Photo caption: Tuck O’Brien of Southold holding the trophy he won for being the most outstanding player at a baseball camp he attended in 1948. (Credit: Jean Dempsey)