During his first two years in the Motor City, Probert bounced between the Wings and the minors. In 1987-88, however, he caught on in a big way, scoring plenty of points and establishing himself as one of the most feared enforcers in the NHL. He was once described as the most powerful combination of power and skill this side of Mark Messier. But as Red Wings insiders noted, Probert was groomed to lean more toward fisticuffs than toward the development of his playing skills. As such, he is most remembered for punching a wide swath across the NHL.

After receiving a lifetime ban from the NHL for drug possession, Probert was sent to serve a six-month prison sentence in Minnesota, he entered a rehab program that brought about a recovery sufficient enough to get his ban from hockey lifted.

Late in the 1989-90 campaign, Probert was reinstated in the NHL with the Wings. He picked up his career where he left off, as a fighting man with a long reach and a willingness to stir up trouble around the goal crease.

A second offense would haunt Probert in the mid 1990s. All appeared to be well until days after he's signed as a free agent with the Chicago Blackhawks in the summer of 1994. Probert would be involved in motorcycle accident while under the influence, crashing his motorcycle into a car. As a consequence, Probert was suspended indefinitely from the NHL before making it back to the NHL in 1995-96 with the Blackhawks.

Upon his return to the Blackhawk lineup in 1995-96, Probert went to play six more seasons with the team before retiring at the end of the 2001-02 season.

Tragically, Probert passed away on July 5, 2010 after collapsing on a boat on Lake St. Clair, leaving behind his wife and four children.