1955, 1957,
1959-1960, 1978-1993


Haywood Sullivan was born on December 15, 1930, in Donalsonville, Georgia. He played both football and baseball in high school and was considered a blue-chip quarterback. Upon leaving high school, he was heavily recruited to play football by both Auburn and Alabama, but chose Florida. He was named All-SEC quarterback with some thinking he was good enough to have been All-American. He was also a standout on the baseball field and was referred to as a man among boys. 

Haywood received a great deal of attention from major-league scouts. In the end, the Boston Red Sox offered him a $75,000 bonus. He signed with the Red Sox in June 1952, thus ending his football career.

He began his minor league career with the Albany (New York) Senators. In 1953 he was thought to have a good shot at the third-string catcher job, but it came to an end in March, when he was forced to leave the team before reporting to the Army.

While in the service, he played quarterback for the Fort Jackson, South Carolina football team and also played baseball. He missed two baseball seasons to military service, but returned in 1955 with the Double-A Louisville Colonels as one of baseball’s best catching prospects. He made his major-league debut in September at Fenway Park. 

In 1956, he was named an all-star again with the San Francisco Seals of the Pacific Coast League, then the Red Sox top affiliate. Coming into the 1957 season, he was thought to have a shot to stick with the Sox. He made the Opening Day roster, and played two early season games, but in May, was optioned to the Miami Marlins.

In 1958 Haywood was in the mix once again, hoping to make the team. Sammy White had been Boston’s catcher for six years, but Haywood had an opportunity because of his badly needed right-handed power. Unfortunately, he suffered a badly-broken right index finger during a preseason game against the Washington Senators and was sidelined for several weeks. Shortly after, he developed back trouble and it was soon determined he had a slipped disk and needed an operation. He missed the entire 1958 season but arrived at spring training in 1959, fully recovered.

Haywood began the season as the Red Sox third string catcher, but rarely played through June, so he was then demoted to the Triple-A Minneapolis Millers. He began the 1960 season, sharing the catching duties on the Red Sox. In June, the Sox acquired catcher Russ Nixon from the Indians, who promptly took over as the starting catcher.

In December 1960, Haywood's tenure with the Red Sox came to an end, when he was selected by the new Washington Senators in the 1960 expansion draft, but the Senators sent him to the Kansas City Athletics two weeks later.

In 1961 he spent a majority of his time behind the plate but also played first base and both corner outfield positions. He played two more seasons with the Athletics but he never became the offensive catcher people thought he would.  In July 1963 he joined the Triple-A Portland Beavers as a player/coach, and decided to put an end to his professional baseball-playing career to pursue a managerial post within the Kansas City farm system.

In 1964 he skippered the Birmingham Barons of the Southern League. The next year, he was placed in Triple A, to manage the 1965 Vancouver Mounties. In May, he became the Athletics’ new manager. 

In 1966, Haywood took the position of Director of Player Personnel with the Red Sox. Returning to the team who had first signed him, he would work under newly promoted general manager Dick O’Connell. In the early 1970s when he had become the director of amateur scouting for the club. 

He maintained a very close relationship with Tom Yawkey and his wife Jean. He worked under O’Connell and Yawkey for 12 seasons, had become Yawkey’s liaison man and confidant, and a very close friend.  In July 1976, Tom Yawkey died and the Red Sox were put up for sale a year later.

A group headed by Haywood and former Red Sox trainer Buddy LeRoux was awarded the franchise, though theirs was not the highest offer. In October 1977, in a event engineered by Mrs. Yawkey herself, Dick O’Connell and two other team officials were fired and Haywood was named general manager. In December 1977, the sale of the Red Sox to Sullivan and LeRoux was rejected by the American League.

In March 1978, Jean Yawkey became a full general partner when she donated Fenway Park valued at $5.5 million, plus $1 million in cash to the Sullivan-LeRoux group. The deal was approved in May and the trio officially took over full control of the club. Haywood remained the general manager with Boston until February of 1984. During his six seasons as GM, the Red Sox posted a 499-416 record, a .545 winning percentage. 

Before the 1981 season, he trading Rick Burleson, Butch Hobson, and Fred Lynn and most famously, letting Carlton Fisk become a free agent after he failed to offer Fisk player a contract before the deadline set forth by Major League Baseball. As a result, he and LeRoux became unpopular with Boston fans.

Baseball was changing and lacking the money Yawkey often poured into the club, the team suffered. The organization was having a hard time adjusting to free agency he and the relationship between the trio began to deteriorate as the seasons went on.

In June 1983, on a night meant to honor former star Tony Conigliaro, Buddy LeRoux, acting on behalf of limited partners Al Curran and Rogers Badgett, declared war. Before a scheduled general partners’ meeting, LeRoux informed everyone that he was seizing control and announced that he was firing Sullivan. The two sides met in court and the judge ruled in favor of Sullivan and Yawkey.

Following the 1983 season, Haywood voluntarily gave up his seat as general manager to the newly hired Lou Gorman and became the team’s chief executive and chief operating officer. Mrs. Yawkey lived until 1992 and upon her death, her representative John Harrington bought out Sullivan. 

Haywood Sullivan became a real estate developer in Fort Myers and also ran a marina. He died in Fort Myers, Florida from a heart attack, at the age of 72, on February 12, 2003.