After graduating from Chicago's Kennedy High School, Hickey went to the University of Texas-Pan American and was a first-team All-American in. He went 16-2 in 19 starts with a 1.66 ERA and helped his team win 64 games, a school record. That season, his senior year, his 16 victories led all NCAA baseball. In that season, of his 19 starts he recorded 16 complete games; those 16 complete games were the third largest single season total in NCAA history at the time, and still rank 4th all-time. While at Pan American he was a member of Phi Sigma Kappa fraternity. Hickey was drafted in the 13th round of the 1983 MLB Draft by the Chicago White Sox. His best career season was in, when he went 13-5 and had a 1.81 ERA in 49 relief appearances for the Single-A Appleton Foxes who were the champions of the Midwest League that year. He played in the White Sox' minor leagues from 1983 to. In, Hickey pitched for the Double-A San Antonio Missions in the Los Angeles Dodgers organization. In, he played for the Double-A Columbus Mudcats in the Houston Astros organization in what would be the final year of his playing career.
Coaching career
Starting in, Hickey became the pitching coach for two seasons at the Houston Astros' Double-A affiliate in Jackson where his staff led the Texas League with 939 strikeouts in. In, Hickey was promoted to pitching coach for the Astros' Triple-A affiliate, the New Orleans Zephyrs. That year, the Zephyrs won the first-ever Triple-A World Series, pitting the PCL champion against the International League champion. In, the Zephyrs had the second-best ERA in the PCL en route to the Pacific Coast League championship. In 2002, Hickey was named a coach for the All-Star Futures Game in Milwaukee and also was a member of the coaching staff for the Triple-A All-Star Game. At the end of the 2002 season, he was named the Astros Player Development Man of the Year. In 2002 and, Hickey's pitching staff led the Pacific Coast League in ERA with a 3.40 mark and a league-leading 11 shutouts. Hickey was announced as the interim pitching coach for Houston on July 14,, and was named the full-time pitching coach in October 2004 after 14 seasons as a pitching coach in their minor leagues and 7 with the Zephyrs. In his first year with Houston, he helped the pitching staff which included Roger Clemens, Brad Lidge, Roy Oswalt and Brandon Backe advance to the 2004 National League Championship Series. In, the Astros advanced to the World Series, with Clemens, Andy Pettitte, and Roy Oswalt in the National League in ERA. Houston was also second overall in the NL with a 3.51 ERA in 2005, and led the league with the fewest runs and walks allowed. On November 18,, Hickey was announced as the new pitching coach for the Tampa Bay Rays, replacing Mike Butcher. After the 2017 regular season, the Tampa Bay Rays and Hickey parted ways. In the 2017 offseason, Hickey joined the Chicago Cubs as their pitching coach, coming along with two new coaches. Hickey reunited with manager Joe Maddon as the two were together at Tampa Bay until 2014. Hickey replaced Chris Bosio, who had been with the Cubsthe past six seasons.
