Rising Through The Red Sox' Ranks
Two years later, O'Connell joined Boston's front office in an administrative capacity. He rose through the ranks, serving as "home secretary" and director of stadium operations, then became the Red Sox' business manager during the late 1950s. It appeared that he would rise no further. Tom Yawkey, the team's owner since 1933, wanted famous former players to head his organization, and through 1960 his three general managers — Eddie Collins, Joe Cronin and Bucky Harris — were all current or future members of the Baseball Hall of Fame. With the Red Sox' great left fielder, Ted Williams, about to retire, and with the team's fortunes at a low ebb, Yawkey fired Harris in September 1960 and informally offered the GM post to Williams. But the future Hall-of-Fame hitter was not interested in an office job; he preferred to fish and teach hitting in spring training.
As the GM seat lay vacant — but perhaps being kept warm for Williams, who was named an "executive assistant" to Yawkey — O'Connell was promoted to executive vice president; meanwhile, field manager Pinky Higgins, who had become a friend of Yawkey's, staked out a position as the top "baseball man" in the Red Sox organization. The New York Times reported on October 1, 1960, that Higgins would assume responsibility for all player personnel decisions in the Boston organization. Indeed, the club spent the 1961 and 1962 seasons without a full-time general manager. Although O'Connell is listed by the Red Sox media guide as de facto GM, he likely focused only on the business aspect of the job; it is unclear (and doubtful) that he had any baseball operations role. Higgins shed his on-field responsibilities and formally became executive vice president/GM at the close of the 1962 season.
In the early 1960s, Boston overhauled its farm system and scouting operation and was beginning to produce outstanding talent, but the big league Red Sox continued to struggle and attendance dwindled. Finally, during the closing days of a dispiriting 100-loss 1965 season, Yawkey fired Higgins and offered the general manager title to O'Connell on September 16.
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