Front Office and Ownership Career
In November 1965, he was recruited by the Red Sox, who had reorganized their front office under new general manager Dick O'Connell. As vice president, player personnel, Sullivan was positioned as the top "baseball man" in the organization, and from 1965-67 was instrumental in acquiring several players from the Athletics (such as José Santiago, John Wyatt, José Tartabull and Ken Harrelson) who would help lead Boston to its surprise 1967 AL pennant. But O'Connell gradually assumed more power and took over most of Sullivan's responsibilities; during the early 1970s, Sullivan kept his title but in reality became the Red Sox' director of amateur scouting.
Despite his decline in overall authority, Sullivan maintained very close personal ties with owner Tom Yawkey and his wife, Jean. In 1977, a year after Tom Yawkey died of leukemia, the Red Sox were put up for sale. Sullivan — reportedly borrowing $100,000 and using his home as collateral — joined an ownership group organized by former Red Sox athletic trainer Edward "Buddy" LeRoux. Because of Sullivan's close friendship with Jean Yawkey, the LeRoux offer was accepted, even though it was not the highest bid and the group did not have the financial resources of some of its rivals. The American League initially rejected the deal, but reconsidered when Mrs. Yawkey joined the group as a third general partner in 1978.
Before the sale was consummated, in October 1977, Mrs. Yawkey fired O'Connell and promoted Sullivan to general manager. Overall, his first off-season as GM of the Red Sox was highly successful. Still using the resources of the Yawkey fortune, and benefitting from the depth of the Red Sox farm system that he helped to build, Sullivan acquired players such as Mike Torrez, Jerry Remy, Dick Drago, Tom Burgmeier and Dennis Eckersley. Buoyed by the new additions to an already strong team, the Red Sox charged into first place in the 1978 AL East race. The Red Sox would lose a 14½ game lead over the New York Yankees and a one-game playoff that season. Although manager Don Zimmer is usually cast as the chief culprit for the collapse, Sullivan contributed to the debacle by dealing away useful players such as Bernie Carbo, Ferguson Jenkins, Jim Willoughby and Reggie Cleveland, who were considered to be "clubhouse lawyers." None of the players fetched comparable value, and the loss of pitching and bench strength was a critical factor in Boston's struggles.
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