Gutiérrez was the Baltimore Orioles' second selection in the 1988 MLB Draft, the second of four compensatory supplemental picks between the first two rounds. After falling behind Manny Alexander on the organization's depth chart at shortstop, Gutiérrez was sent to San Diego on September 4, 1992 to complete a transaction made four days earlier on August 31 when Erik Schullstrom was also dealt to the Padres for Craig Lefferts. Listed at 6'1", 195 pounds, Gutiérrez started his career at shortstop and became a valuable utility player later in his career. In the field, he had decent range and an above-average arm. He was a sharp line-drive hitter, and spent most of his career in the National League. His most productive season came in 2001 with the Cubs, when he posted career-highs in batting average, RBI, runs, hits and games played. He finished the year leading the National League in sacrifice hits. He also had the fourth most sacrifice flies in the league, and was tenth in singles.
On July 21, 2004, the Boston Red Sox acquired Gutiérrez from the Chicago Cubs for a player to be named later or cash considerations. Red Sox General ManagerTheo Epstein lauded Gutiérrez as "a veteran with a tremendous makeup... he'll fit in well as a utility guy for us." Gutiérrez wore number 16, the same number as other Red Sox players such as Jim Lonborg, Hank Johnson, Dave Sax and Bob Zupcic. His greatest offensive performance came on August 28, 2004 versus the Detroit Tigers. Gutiérrez, who filled in at second base while Mark Bellhorn took over at third for Bill Mueller, went 3 for 4 with a two-run single with the bases loaded in the fifth inning. Teammate Alan Embree was in awe: "He's been sitting a long time, to come off the bench and contribute like he did tonight was incredible." After winning the World Series, Gutiérrez carried an industrial-sized broom to remind victory parade goers of the final tally. While with the Red Sox, Gutiérrez was a.275 hitter with 3 RBI in 21 games, including 6 runs, 1 double, 1 stolen base, and a.310 on-base percentage. The Red Sox were 14-7 in games in which Gutiérrez appeared. Over an 11-season career, Gutiérrez was a.268 hitter with 38 home runs and 357 RBI in 1074 games, including 463 runs, 138 doubles, 25 triples, 49 stolen bases, and a.338 on-base percentage.
