While a successful player by some measures, including being voted to the 1987–88 Campbell Conference all-star team, Probert was best known for his activities as a fighter and enforcer, as well as being one half of the "Bruise Brothers" with then-Red Wing teammate Joey Kocur, during the late 1980s and early 1990s.

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.

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.

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.

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.

[6] One of the more noteworthy occurrences of his career with Chicago is that he scored the final NHL goal at the historic Maple Leaf Gardens on February 13, 1999.

[9] Some significant tilts in Probert's career include:[citation needed] 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.

Probert, along with former teammate Joe Kocur, is featured in a book entitled Bruise Brothers by Bob Duff.

[16] Before his death, Probert had been working on a memoir with Kirstie McLellan Day, co-writer of Theo Fleury's bestselling autobiography Playing with Fire.

His activities as a Red Wings alumnus were somewhat limited by the fact that, due to his criminal history, he required an immigration waiver each time he wanted to cross the border.

On January 2, 2007, Probert appeared along with many other former Red Wings teammates to honor the retiring of Steve Yzerman's number 19 at Joe Louis Arena.

[19] Probert worked on the Mike Myers 2008 film The Love Guru, making a cameo as a hockey player.

[21] On June 4, 2004, Probert was arrested for allegedly parking his BMW sport utility vehicle on the wrong side of the street and entering into an altercation over drugs with bystanders.

His stepfather-in-law, Dan Parkinson, the Cornwall, Ontario chief of police, attempted CPR to save his life.

[27][28] Funeral services were held July 9, 2010, in Windsor, Ontario, and attended by several former teammates and opponents,[29] including Dino Ciccarelli, Tie Domi, Chris Nilan, Gerard Gallant, Doug Gilmour, Stu Grimson, Joey Kocur, Petr Klima, Brad McCrimmon, Darren McCarty, and Steve Yzerman, as well as Red Wings general manager Ken Holland and owners Mike and Marian Ilitch.

[29] Probert's family announced, on September 25, 2010, that his brain would be donated to the Sports Legacy Institute to assist researchers who are studying the effects of concussions and other sports-related head injuries.

[31] In March 2011, it was reported that researchers at Boston University had found evidence of chronic traumatic encephalopathy in Probert's brain.

[32] On Sunday April 9, 2017, Probert's family spread his ashes in the Red Wings penalty box at Joe Louis Arena's final game.