In his 21-year Major League Baseball (MLB) career, he played for the Minnesota Twins, Chicago Cubs, San Francisco Giants, Baltimore Orioles, Colorado Rockies, New York Yankees, Houston Astros, Milwaukee Brewers, Los Angeles Angels of Anaheim, New York Mets, and Toronto Blue Jays.

Born and raised in Gary, Indiana, Hawkins was a seventh-round draft pick of the Twins out of high school.

After posting some of the worst earned run averages (ERA) in the American League (AL) in 1998 and 1999, Hawkins was moved to the bullpen in 2000.

He struggled as the Twins' closer in 2001 but found better success thereafter in a setup role, posting a career-low 1.86 ERA in 2003 and reaching the playoffs in 2002 and 2003 with Minnesota.

In 2004, the Cubs signed Hawkins to set up for closer Joe Borowski, but he blew several saves and became unpopular with the team's fans.

[2][6] He spent the next four years in the Twins' minor league system before making the team's starting rotation out of spring training in 1995.

[1][7] His MLB debut on April 29, 1995, was a disastrous start against the Baltimore Orioles, where he gave up seven earned runs on seven hits in only 1+2⁄3 innings of work.

[8] After losing his first three starts, Hawkins was demoted to the Salt Lake Buzz of the Triple-A Pacific Coast League in May when the Twins had to shrink their roster.

Twins manager Tom Kelly, unable to decide who he wanted as his full-time closer, used both Hawkins and Bob Wells in the role throughout the year.

[29] For the second year in a row, the Twins won the AL Central Division title, this time facing the New York Yankees in the ALDS.

[4][32] On September 11, Hawkins threw an immaculate inning, striking out the side on only nine pitches in a game against the Florida Marlins.

[34][35] The blown saves earned him the ire of Cubs fans, who made a habit of booing him loudly at Wrigley Field when he came on in relief.

[10] On May 28, the Cubs traded Hawkins to the San Francisco Giants in exchange for pitchers Jerome Williams and David Aardsma.

[10] With the Giants, Hawkins assumed an eighth inning setup role, frequently preceding closer Tyler Walker.

[10] On December 6, Hawkins was traded along with cash considerations to the Baltimore Orioles for left-handed reliever Steve Kline.

[10][41] With the Orioles in 2006, Hawkins served as the eighth inning setup man for closer Chris Ray.

"[44] On December 5, 2006, Hawkins signed a one-year, $3.25 million contract with the Colorado Rockies, who wanted him to serve as the eighth inning setup man for closer Brian Fuentes.

[10] At the end of the regular season, the Rockies forced a tie-breaker game against the San Diego Padres to determine the NL wild card team.

[52] On May 20, during a game against the Baltimore Orioles, Hawkins threw a head-high pitch over left fielder Luke Scott.

[27][73] In the NLCS against the Cardinals, he was not charged with a run in three appearances, but he did allow two inherited runners to score in Milwaukee's 12–6 loss in Game 6.

[10] On September 27, Hawkins made his 1,000th career appearance in a game against the Los Angeles Dodgers and promptly got Darwin Barney to fly out to right field.

[64] After posting a 2–1 record, two saves, and a 3.63 ERA in 24 games, he and teammate Troy Tulowitzki were traded to the Toronto Blue Jays for José Reyes, Jeff Hoffman, Miguel Castro, and Jesús Tinoco on July 28.

[95] Hawkins made 18 regular season appearances for the Blue Jays, pitching to a 1–0 record with a 2.76 ERA and 14 strikeouts in 161⁄3 innings.

[10][96] He made two appearances in the ALCS but allowed five runs in one inning pitched as the Blue Jays were eliminated in five games by the Royals.

[10] Bob Nightengale of USA Today voted for Hawkins in the 2021 Baseball Hall of Fame balloting.

The clause reads, “Voting shall be based upon the player’s record, playing ability, integrity, sportsmanship, character and contribution to the team(s) on which the player played.”[98] Though Nightengale was unaware of it at the time, Hawkins garnered a second Hall of Fame vote from someone else, but this was not enough for him to be eligible for future ballots.

[101] Eventual Hall of Famer Ken Griffey Jr. was so impressed with the pitch, he asked to see Hawkins once when the Seattle Mariners were playing the Twins at the Metrodome.

[88][3] Hawkins' half-brother, Ronald Sewood, was sentenced to prison in 1996 at the Federal Correctional Institution, Milan.

[2] Hawkins is the godfather of his Minnesota Twins teammate Pat Mahomes' son, Patrick II who is a quarterback for the Kansas City Chiefs.

[4] In January 2021, Hawkins and his wife paid for a woman who caught a home invasion on TikTok to move into an apartment with better security.