Gutiérrez began his professional baseball career in 1978 with the Elmira Pioneers, a farm team of the Boston Red Sox. He reached the Triple-A level in 1983.
Gutiérrez reached the major leagues with Boston in 1983, playing in parts of three seasons with the Red Sox, including a career-high 151 games in 1984. The third native Colombian to play in MLB, he was the Red Sox's starting shortstop in 1984 and into the first two months of the following campaign. A knee injury sustained in a 10–3 loss to the Texas Rangers at Arlington Stadium on May 25, 1985 led to him being supplanted by Glenn Hoffman and unable to reclaim the position as he ended 1985 with 23 errors and a .218 batting average that was 45 points lower than from the previous year.
He was traded from the Red Sox to the Orioles for Sammy Stewart on December 17, 1985. Upon hearing reports that Gutiérrez was released by two winter ball teams in the Dominican Republic and Venezuela because of erratic behavior which involved frequent fights, the Orioles attempted to have the transaction restructured or voided, alleging that the Red Sox had prior knowledge of any such issues. American League president Bobby Brown upheld the deal on March 11, 1986, ruling that it was made in "good faith, with neither club knowingly misrepresenting the facts" and that "the Orioles' request to rescind the trade has been denied."

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