Bob Chakales was born on August 10, 1927, in Asheville, North Carolina. He hadn’t played any organized baseball in Asheville, but played a lot of true sandlot ball. Baseball became more interesting to Bob after the family moved to Dunn, NC.

Bob (or Chick as he was known in childhood) played as a third baseman in Dunn, and also played American Legion ball, again at third – the position where the team had the greatest need. Then in the final game of the season, when the games began to pile up and the team needed an extra pitcher. His coach asked him to pitch. He did well, winning his first outing.

Bob opened the next American Legion season with a victory in an 18-strikeout performance. He wound up pitching Dunn into the state finals and was named outstanding pitcher of the tournament.

Baseball wasn’t the only sport at which he excelled at the state level. Marble shooting was a big deal, especially in the South. When he was a youth, he went all the way to the top, winning the North Carolina state marble shooting contest. 

The family moved to Richmond, Virginia where Bob enrolled at Benedictine High School, a small private boys’ Catholic school with strong sports programs. His tuition was gratis – and even though it was a military school, he was not required to wear the military uniform, because the sports uniforms were sufficient. The school apparently drew quite well, having good athletes on their teams. 

Bob became the quarterback on the football team, and was named all-state in basketball and baseball. In 1944, he struck out 99 batters in 69 innings for Benedictine and was selected All-State in baseball, basketball, and football. On the ballfield that spring, he won eight games in a row, including a no-hitter, and led all Richmond batters in hitting with a .523 average.

He was offered scholarships to a wide variety of colleges across the South, but before accepting any he responded to a telegram from the Philadelphia Phillies, offering a tryout. In June, 1945, the Phillies signed the 17-year-old to a contract with an additional bonus earmarked for his college education. Although the Phillies provided him with college education money, he never did go to college. The college fund was, however, put to good use. 

The Phillies first sent him to their Single-A affiliate, the Utica Blue Sox. He lost his first three games and was sent down  to Class B Wilmington, Delaware, where he pitched in the Interstate League for the Wilmington Blue Rocks. He posted a 13-5 record with a 5.06 ERA, and was one of the best batters on the team, hitting .327. 

Though World War II was over, there was still a need to cycle in new soldiers, while letting those who had served come home. In November 1945, he passed his physical and was inducted into the Army.  Fort Lee in Virginia was glad to have a pitcher going for its team and by early August, the Fort Lee Travelers had established themselves as state semipro champions and flew to the national semipro tournaments in Wichita. Bobs was 7-3, with 119 strikeouts, and was hitting well in the Army too, batting .340. He was elected to the All-America semipro team. 

His service commitment complete, Bob began pitching for Utica again in April 1947. He had mixed results throughout the season, with an ERA of 5.36, walking 76 batters in 94 innings.

Bob tried out with the Phillies in Clearwater during spring training 1948, and was again assigned to begin the season pitching for Utica, but hurt his arm trying to work a curveball. Once more, he was moved to a lower level and was sent to Maine, joining the New England League’s Portland Pilots in early June. The Cleveland Indians took him in the minor-league draft in November of 1948. He was sent to Oklahoma City, part of the Indians system. 

In 1949, he played with the Single-A Wilkes-Barre Barons. He pitched the Barons right into the championship game against the Binghamton Triplets in the Governors Cup finals, in September.

His arm got better, and he became the main pitcher for the Barons in 1950 and threw the Eastern League title-clinching game on September. The Barons easily beat Binghamton, four games to one in the Governors Cup. After the season he was named the top pitcher in the Eastern League.

Bob reported to Tucson for spring training in 1951 with the Indians and debuted in Cleveland on April 21, 1951. He was a good batter and over his four seasons with the Tribe, he hit .353 in 34 at-bats. 

He had just one start for the Indians in 1952, winning the next to last game of the season. He’d spent most of the year in Indianapolis, playing for the Indians’ Triple-A club. He labored with a 5.18 ERA in Indianapolis and was recalled nonetheless in September.

In 1953, Bob opened the season with the big-league ballclub and played most of the year with the Indians, though he appeared in only seven games, before he was optioned to Indianapolis in July. He was recalled in September, but saw no further action. That winter he pitched for Gavilanes in the Venezuelan League.

He opened the 1954 campaign in Cleveland, where he helped the Indians off to their best season in their history. The Indians went to the World Series in 1954, but without Bob, who in June, was traded to the Baltimore Orioles. With Baltimore, he was 3-7 in 1954, though his 3.73 ERA was slightly better than the team average.

In December, he was packaged in a seven-player trade from the Orioles to the Chicago White Sox. He got very little work in the first part of 1955, and then was packed off to Washington. Bob was their main man for relief, but he struggled because his arm was dead.

By early June of 1956, he was considered a surprise performer with a 1.94 ERA through his first 14 outings. He pulled a tendon in his elbow, however, and suffered a sore arm for much of the year, but soldiered through the season, appearing in a club-high 43 games.

Over the wintertime, Bob opened his own restaurant in Richmond, called Blair’s. It was his second venture in the field, having owned and operated one on Maryland’s Eastern Shore in the winter of 1955. 

In 1957, the Senators sent him and pitcher Dean Stone to the Red Sox for infielder, Ted Lepcio, pitcher Russ Kemmerer, and outfielder Faye Throneberry. In August, the Sox purchased Murray Wall from Dallas and optioned Bob to their San Francisco Seals farm club. After the Coast League season ended, he was brought back to Boston, where he appeared in one final game, in September.

During Bob’s year at Boston, he and Ted Williams became close friends. Bob often stayed in the hotel room registered for Williams to shield him from the media. Bob and Ted continued to get together after they had retired from baseball. During five straight years in the 1970s, they met during the Preakness horse race in Baltimore. Before memorabilia was big, Ted signed an official Genuine Louisville Slugger with his name engraved on it and gave it to Bob. Not knowing the value of the bat, his son James, broke the gift from Ted in a sandlot game.

In January of 1958, the Red Sox announced the outright sale of Bob to Minneapolis, who had replaced San Francisco as the Red Sox top farm club. When Minneapolis had seen enough, they sent him to his hometown team, the Richmond Virginians, part of the Yankees’ system. That December, Richmond sold him to the Toronto Maple Leafs. 

Bob got in a fairly full season for the unaffiliated Toronto Maple Leafs in 1959 and the Indians took on Toronto as their Triple-A affiliate in 1960, and so he was back in the Cleveland system. In 1961 he split the season, with Toronto and then the Hawaii Islanders (in the Pacific Coast League, affiliated with the Kansas City Athletics.) The 1961 season was his last in professional baseball. 

In the major leagues, he’d been used more as a reliever than a starter, with 162 of his 295 appearances coming in relief roles, but most often in long relief. He was 15-25 with a 4.54 ERA, starting only 23 of his 171 games.

Bob loved golf, and thought about going pro with a 1 handicap. But instead he contacted the United States Golf Association, found out how to register as a golf course contractor and built a par-3 course in Richmond. A general contractor from Charlotte, heard about the course and reached out to him. The two formed a partnership and began to build courses. They built championship courses and started with a nine-hole course and then went on to build course after course. In the end they built nearly 200 golf courses and Bob became president of the Golf Course Builders Association of America. Bob built the original TPC Sawgrass Course in Ponte Vedra Beach, Florida.

Bob Chakales died on February 18, 2010 in Richmond. He was 82 years old.