Drafted by the Cubs in the 33rd round of the 1991 Major League Baseball draft, Jennings made his Major League Baseball debut on April 18, 1996, and appeared in his final game on October 7, 2001. He played in a total of 93 games, batting .244 in 213 at-bats, with three home runs and 24 runs batted in (RBI).\n', '

He was traded twice in July 2001. The Oakland Athletics sent him to the Colorado Rockies for Ron Gant on July 3. He played in only one game for the Rockies, and was traded to the Cincinnati Reds on July 19.\n', '

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