By August Jack was again in contention for the RBI title, but he had become increasingly unhappy. When the Boston Globe quoted an "informant" as saying Jackie would retire at the end of the season, across the country the Oakland Tribune simultaneously quoted Zoe Ann as saying that Jackie was more serious than ever before about quitting. The next day a rumor surfaced (8-3-59) that Jack might be traded to the Giants, where he could play at least half the season closer to home so he wouldn't have to end his career, Manager Bill Rigney said he'd welcome Jack to the team; but Jack wouldn't give reporters verification of his decision-simply because it hadn't been made. He was determined to wait until after the season and was sorry a story had broken so soon about one of his considerations.

Throughout the season (in which the Red Sox finished a disappointing fifth place), Jack was again the one to catch for the RBI title, even though he played in the fewest games since he left the Yankees in 1952. Retirement weighed heavily on his mind, for his performance-though better than 90 percent of all other ballplayers'-was slipping. He ended the season in glory, however: In his final contest against the Senators, he tied the score in the ninth inning by doubling home two runs, then went on to win the game with a homer (his twenty-eighth) in the eleventh inning. However, his number of runs batted in had dropped by ten, his home runs by seven, and his batting average to just .277. In fact, the RBI title didn't seem to mean anything to him, as he declined to play in a second game against the Senators at a time when Rocky Colavito of the Cleveland Indians trailed Jackie by only a few RBIs but went hitless in four at-bats later that day against the Athletics.

Jack had been eager to get home the last day of the season, September 27, so he obtained permission to skip that final game so to catch the two o'clock train. When asked about his future, Jackie replied, "I plan to decide on my future in three or four weeks. I want to let Mr. Yawkey know in case it affects any trades he might have in mind for the winter. In October Jack began to look seriously into becoming a home-building contractor in Lake Tahoe and starting a second Bow and Bell at the south end of the city to take advantage of the forthcoming Olympics. By early the next month came word from Bucky Harris that "Jensen won't be traded." Speculation about Jackie's retirement continued through the rest of the year until the last week of January 1960, when Jack told the Associated Press in Los Angeles that he had turned down a generous offer by the Red Sox to return.

Ironically, Jackie was one of nineteen sluggers from fifteen major league teams to participate in the Home Run Derby (see appendix L) between seasons, becoming the third-highest winner. Despite five homers in a row, he lost to Mickey Mantle 10-13 in one game and 2-9 in another. However, he beat Rocky Colavito 3-2, and, in what was described later by David Gough as the most exciting game of the series, beat Ernie Banks, his National League MVP counterpart, 14-11.

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