Prior to playing with the Detroit Red Wings, Probert was with the
Brantford Alexanders of the
Ontario Hockey League. After being drafted, he spent one more season with the Alexanders before spending his 1984–85 season with both the
Hamilton Steelhawks and the
Sault Ste. Marie Greyhounds of the
OHL.
Detroit Red Wings (1985–1994) Probert was drafted as the fourth pick in the third round (46th overall) in the
1983 NHL entry draft, in which the Red Wings also selected Kocur and
Steve Yzerman. During the 1985–1986 and 1986–1987 seasons, Probert spent the majority of his time with the Red Wings while occasionally playing for their minor league affiliate
Adirondack Red Wings of the
American Hockey League. In the 1985–1986 season, he finished third on the team in penalty minutes behind Kocur and
Randy Ladouceur, both of whom played more regular season games than Probert. In the 1986–1987 season, Probert accumulated only 24 points, but amassed 221 penalty minutes. The 1987–1988 season was the pinnacle of Probert's career. He cemented his reputation as an enforcer with a league-leading 398 penalty minutes, the sixth-highest single-season total in NHL history. He also tied for third on the team with 62 points, and played in his only
NHL All-Star Game. In addition he contributed the most points during the Red Wings' playoff run, in which Yzerman missed all but the final three games with a knee injury. Probert's career hit a snag in 1989 when he was arrested for
cocaine possession while crossing the Detroit–
Windsor border. U.S. Customs agents at the
Detroit–Windsor Tunnel found 14 grams of cocaine hidden in Probert's underpants. He served three months in a federal prison in
Minnesota, three more months in a halfway house, and was indefinitely suspended from the NHL. The NHL lifted the suspension at the conclusion of his prison term. Probert was initially ordered to be
deported to Canada following his conviction, but he immediately filed for an appeal. The appeal process allowed him to resume his career with the Red Wings, but barred him from traveling with the team to Canada, as he would not be allowed to return to the United States. The matter was resolved on 7 December 1992, when the
Immigration and Naturalization Service granted his appeal, restoring his travel privileges between the United States and Canada. When Probert returned to the Red Wings, he was temporarily one of the alternate captains of the team along with
Gerard Gallant. While his penalty minutes remained high, he also averaged 40 points a season. During his last season with the Red Wings, he accumulated only 17 points for the team. At this time, Probert once again got into trouble with the law. On 15 July 1994, he had minor injuries when he crashed his motorcycle into a car in
West Bloomfield Township, Michigan.
Police determined that his
blood alcohol level was approximately triple the legal limit, and that there were also trace amounts of cocaine in his system. At the time of the accident, Probert had been ruled an unrestricted
free agent. On July 19, the Red Wings announced that they would not offer him a contract. "This is the end," said senior vice-president
Jim Devellano. "[In] my 12 years with the organization ... we've never spent more time on one player and his problems than we have on Probert."
Chicago Blackhawks (1995–2002) Probert signed with the Chicago Blackhawks on July 23, 1994, but was placed on inactive status by commissioner
Gary Bettman in September 1994 while Probert entered rehab following his July 15 crash and subsequent drunk-driving charge. As a result, Probert sat out the
lockout-shortened 1994–95 season before joining the Blackhawks. Probert's first season with the Blackhawks was the last in which he accumulated over 40 points in a season. From then on, his points and penalty minutes gradually decreased. While he never returned to the levels of point production he achieved with the Red Wings, he remained a physical force on the ice and continued many long-term rivalries with other enforcers. Probert also sustained various injuries during his time with the Blackhawks, most notably a torn
rotator cuff injury which caused him to miss most of the
1997–98 season.
Fighting Probert often saw it as his job to protect his teammates, especially Detroit captain
Steve Yzerman. In a 2007 news story, he recalled a time that he sucker-punched enforcer
Kevin Maguire of the
Buffalo Sabres (December 23, 1987) after Maguire attacked Yzerman. Maguire then unsuccessfully attempted to avoid Probert. Some significant tilts in Probert's career include: • A long-standing rivalry with the Toronto Maple Leafs'
Wendel Clark. • Two long fights with
Craig Coxe of the
Vancouver Canucks in the mid-1980s. • A career-spanning series of battles with
Tie Domi of the
New York Rangers,
Winnipeg Jets and
Toronto Maple Leafs. One of Probert's memorable confrontations was also the genesis of Domi's now-infamous belt gesture, where he gestured to the
Madison Square Garden crowd as if he had a championship title belt around his waist, with Domi remarking it to reporters, "He's been heavyweight champ for a long time. I still respect him. I'd been wanting him for three years. I just hope he remembered what got him where he is." • A career-spanning series of fights with longtime enforcer
Stu Grimson, including a fight in December 1993 when the
Mighty Ducks of Anaheim made their first visit to Detroit. • A memorable fight on December 17, 1993, with former teammate
Joey Kocur of the Rangers, during a brawl involving several players from both teams. Probert and Kocur had grabbed the nearest opposing player without realizing who it was, and continued trading punches even after they identified each other. Later on in Probert's career, he would face Kocur a few more times when he was with the Chicago Blackhawks. • A fight on February 4, 1994, against
Marty McSorley, then of the
Pittsburgh Penguins, lasting nearly 100 seconds. • Several bouts against Montreal and Vancouver enforcer
Donald Brashear. • In a game against the Colorado Avalanche on January 12, 1999,
Scott Parker, an aspiring enforcer, skated up to Probert and bared his fists; challenging him to a fight. Parker was at this time heavier, taller and more than ten years younger than Probert. After circling around each other for several seconds the two grabbed each other's jerseys. However the fight was called off after just 11 seconds when Parker was nearly knocked unconscious from four right hands from Probert without throwing one of his own. • Fought
Jody Shelley in each of the three periods in a 2–1 Blackhawks win over the
Columbus Blue Jackets at the
United Center on January 10, 2002. The three fights by the same two adversaries in a single NHL match would next be achieved fourteen years later when
Evander Kane and
Alex Petrovic did it on February 9, 2016.
Community involvement He actively supported young hockey players in the community, and often bought tickets for kids who couldn't afford to go to Red Wings games. He encouraged a young fan in 1989 to pursue sobriety and challenged him to a contest in which he predicted he would surpass him. By August 18, 2011, that man had been sober for 23 years.
Retirement After the
2001–2002 season, Probert was placed on waivers by the Blackhawks. Because he was not picked up by another team, he was advised that his role with the Blackhawks would be limited, or even relegated to playing in the minor leagues again. On November 16, 2002, Probert opted to "unofficially" retire so that he could join the Blackhawks radio broadcasting team. During the 2003 offseason, Probert formally announced his retirement. ==Post-retirement==