Listed at 5 feet 10 inches, 169 pounds, Jackson was born in Waco, Texas, and attended Wiley College. He was signed by the Pittsburgh Pirates as an amateur free agent in 1955 but his first regular major league experience came as a member of the inaugural 1962 New York Mets. As a starting pitcher, he posted an 8–20 record that year. After three more seasons of sixteen or more losses with the Mets, including a second 8–20 campaign, Jackson was traded to the St. Louis Cardinals for Ken Boyer. In 1966, his first year in St. Louis, Jackson had his best season in the majors. He was sixth in the National League in earned run average and ninth in complete games. Unfortunately for Jackson, he also lost fifteen games and, the next year, was used more as a relief pitcher. Those 15 losses gave him a five-year streak of at least 15 losses—the record since 1900 is six. Despite going 9–4 in 1967, he did not see action in the 1967 World Series.
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