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On June 5, 2019, Brashear had another brush with the law when he was arrested for allegedly breaking an apartment window. Police subsequently discovered cocaine in his possession. Brashear made a court appearance on August 12, 2019, and was scheduled to return to court in Quebec City on September 4 to face the cocaine possession charge

In October 2019, it was reported that Brashear was working at a Tim Hortons restaurant in Quebec City owned by Pierre Sévigny.

In November 2014, Brashear stepped out of retirement and signed a contract with Modo Hockey of the Swedish Hockey League (SHL) for the remainder of the season. He scored once on a power play on March 16, 2015 against Vita Hästen, before concluding his professional career at the conclusion of the 2014–15 season.

In April 2011, Brashear signed a three-fight contract with the mixed martial arts promoter Ringside MMA. Brashear's first fight occurred on June 4, 2011, against Mathieu Bergeron at the Colisée Pepsi in Quebec City. In the fight, Brashear immediately charged Bergeron, knocking him down with a right hook. After knocking him down, he continued to hit him with hammer fists, forcing the referee to stop the fight after only 21 seconds. Brashear was officially awarded the win by TKO.

At the end of the season, the Rangers again placed Brashear on waivers, making him eligible for a contract buyout. Instead of buying-out his contract, however, the Rangers traded Brashear on August 2, 2010, along with Patrick Rissmiller, to the Atlanta Thrashers in exchange for centre Todd White. Atlanta then placed Brashear on waivers and bought-out the remaining year of his contract, thus making him an unrestricted free agent. At the end of the 2009–10 season, Brashear ranked 15th all-time in NHL history for penalty minutes.

In the January 2010 issue of The Hockey News, Brashear was named Enforcer of the Decade, noting that although he did not lead the NHL in number of fights, during the decade, he would have been involved in more if "he wasn't so feared." Hockey analyst Bill Clement states that "Brashear has a great sense of when his fighting skills are necessary and he picks his spots before dropping the gloves. He's excellent at understanding when a bit of pugilism might well provide the push or nudge to get some momentum going for his team." The Hockey News also assessed his skills by saying he possessed one of the most intimidating packages in the League, had a decent skating stride and was one of the best pugilists in the NHL. He was a bit too deliberate when handling and passing the puck, and fought much less as he got older, while slowly breaking down over time.

In the 2008–09 season, Brashear's point total dropped to four, his lowest total since 1995–96 while he was with the Montreal Canadiens. During the 2009 Stanley Cup playoffs, he earned a suspension for two separate on-ice incidents. On April 26, 2009, the Capitals faced the New York Rangers in Game 6 of their first-round series. In the pre-game warm-ups, Brashear shoved Rangers enforcer Colton Orr, then delivered a blind-side hit to Blair Betts mid-way through the game's first period. As a result of the hit, and a possible elbow, Betts suffered a broken orbital bone and was out indefinitely. Colin Campbell ruled that the hit was late on an unsuspecting player; he also believed it targeted the head, and as a result caused significant injury. For his actions, Brashear was given a six-game suspension by the League — one for the pre-game altercation and five for the hit on Betts.

Brashear was not given an extension during the season, and prior to the start of the free agency he indicated that he would like to return to Washington, citing the prospect of winning a Stanley Cup. Brashear noted that at his age and place in his career, taking care of his family was his top priority and that money would be the deciding factor in his destination. The Capitals, however, opted not re-sign him. After initial talks with the Kontinental Hockey League (KHL)'s Vityaz Chekhov, he eventually agreed to a two-year, $2.8 million contract with the New York Rangers. At an event for season-ticket holders, Brashear was booed due to the altercation with the Rangers in the previous post-season. He set a personal milestone during the 2009–10 season by playing in his 1,000th NHL game on November 12 against the Atlanta Thrashers.

Brashear has two sons, Jordan and Jaxxson. He separated from their mother, Gabrielle Desgagne, his common-law wife, in 2007. Aside from a half-brother, he does not speak to his birth family. He credits the abuse he suffered at the hands of his father as a child for this.

The Washington Capitals then signed Brashear on July 14, 2006, to a one-year, $1 million contract. The signing was to provide Alexander Ovechkin with some on-ice protection. Capitals management felt that Brashear was skilled enough not to be a liability on the team while bringing an intimidating presence. During the 2006–07 season, the Capitals decided to extend Brashear's contract, signing him to a one-year, $1.1 million contract extension. He was suspended one game by the NHL during the regular season for punching New York Rangers defenceman Aaron Ward following a fight between Brashear and Brendan Shanahan. In the game, Shanahan felt Brashear was taking liberties with Rangers captain Jaromír Jágr, and subsequently challenged Brashear to a fight. Brashear won the fight and motioned as if he was dusting off his hands. Ward then approached him and had words with Brashear, who responded by punching him in the face, earning Brashear a game misconduct for intent to injure and eventually the suspension. At season's end, his point total increased from the previous season to 13 and his 156 PIMs ranked him in the top ten (sixth) in the League for the sixth time in his career. In the 2007–08 season, Brashear played in 80 games for the Capitals, but his offensive production slipped down to eight points while registering only 119 PIMs. However, he served as one of the Capitals' alternate captains. On January 24, 2008, the Capitals once again re-signed Brashear, this time to a one-year, $1.2 million extension.

Following the lockout, Brashear voiced his displeasure with the new way the League called games, stating that the NHL changed the rules to favor "superstars," and he felt that there was no longer a way to "get respect" on the ice. His statement came following a game in which he attempted to fight Darius Kasparaitis, who the Flyers believed delivered a "cheap shot" to Simon Gagné in an Olympic game earlier in the year. After Kasparaitis refused to fight Brashear at various points in the game, Brashear hit Kasparaitis with a gloved punch with 1:53 remaining in the game. Kasparaitis did not fight back, and instead covered up to protect himself. Brashear was assessed 29 PIMs for the incident, including an instigator penalty. Brashear was given a one-game suspension due to new League rules for the 2005–06 season; any player given an instigator penalty in the final five minutes of regulation or overtime would receive an automatic one-game suspension. At the end of the year, he was again in the top ten (eighth) in PIMs, accumulating 166, but his offensive production dropped to a mere nine points. The Flyers opted not to re-sign the enforcer.

Brashear played in 79 games the following season, registering 19 assists and 28 points. After leading the Canucks in penalty minutes for the previous four seasons, Brashear was traded 31 games into the 2001–02 season to the Philadelphia Flyers. The Flyers received Brashear and the Canucks' sixth-round draft pick in 2002 in exchange for Jan Hlaváč and the Flyers' third-round pick in the same draft. While splitting time between the two franchises, Brashear set a career-high in points (32) while also amassing 199 PIMs. In 2002–03, he recorded eight goals, 25 points and 161 PIMs. Thanks in part to his strong work ethic, he was awarded the Pelle Lindbergh Memorial Trophy, an annual award given to the Flyers' most improved player. During the 2003–04 season, he was among the League leaders in PIMs, registering 212, ranking him fifth overall. His PIM total was aided by his role in the most penalized game in NHL history. On March 5, 2004, the Flyers were defeating the Ottawa Senators 5–2, when with 1:45 remaining in the game, Brashear fought Ottawa enforcer Rob Ray. The fight was believed to be in retaliation to Flyers forward Mark Recchi being slashed in the face by the Senators Martin Havlát. Following Brashear's fight, five separate brawls broke out. For his role in starting the fighting, Brashear was assessed 34 PIMs, more than any other Flyer. When asked later why he started the fighting, he responded by saying, "Why wouldn’t I? Did you see the last game?"

Due to the cancellation of the 2004–05 NHL season by the NHL lockout, Brashear signed with the Quebec Radio X of the semi-pro Ligue Nord-Américaine de Hockey league (LNAH). The deal was reportedly worth $300,000. He registered 18 goals and 50 points in 47 games, but was reluctant to fight and felt the League did little to protect him from players wanting to make a name for themselves against an established NHL enforcer. Brashear was suspended from the League following an incident where he continued punching a player in the face while he was lying on the ice.

During the 2004–05 NHL lockout, Brashear spent time as an amateur boxer, compiling a 2–1 record. Later on, he trained with former heavyweight champion Smokin' Joe Frazier In 2007, Brashear, along with some friends, founded the house building company DEC Construction. During the off-season, he works on-site performing various jobs. He has a skill for languages, speaking French and English, while also learning both Russian and Spanish. He enjoys music as well, playing the piano while learning the acoustic guitar. In 2012, Brashear was convicted of assault for a second time after an altercation in a parking lot following a March, 2011, Ligue Nord-Américaine de Hockey playoff game. He was sentenced to 18 months probation and was sued for over $200,000 in damages by the victim in 2014.

During a February 21, 2000 Canucks home game against the Boston Bruins, Brashear was involved in a fight with Marty McSorley. Brashear handily won the fight and, on his way to the penalty box, taunted the Bruins' bench. Later in the game, Brashear collided with Bruins goaltender Byron Dafoe, who had to be taken off on a stretcher with a knee injury. For the rest of the game, McSorley was eager for a rematch with Brashear, who refused to fight again. With 4.6 seconds left in the game, a frustrated McSorley finally swung his stick toward Brashear's head from behind and struck him with a two-handed slash to the right temple. Brashear collapsed to the ice immediately, with his helmet falling off as the back of his head struck the ice. He suffered a seizure and the slash resulted in a grade-three concussion. Canucks goaltender Garth Snow then tried to fight McSorley, but a pile-up occurred, and Snow couldn't get at McSorley, who was ejected with 2.8 seconds left in the game. McSorley later received an indefinite suspension from the NHL and was charged with assault with a weapon as a result of his actions.

In 2000, Brashear was charged with assault following an altercation with a neighbour in the weight room of their townhouse complex in Vancouver. According to court documents, Brashear grabbed the neighbor around the throat and pushed him after the man had complained about Brashear's infant son Jordan crawling on the exercise equipment. "That's no way to show my boys how to solve their problems", Brashear said after the guilty verdict, also lamenting the fact that he had trouble controlling a violent temper inherited from his father. He would ultimately receive six months probation after pleading guilty to common assault and granted a conditional discharge.

The following season, 1997–98, Brashear led the NHL in penalty minutes and set a Canucks franchise record with 372 PIMs, while adding 18 points. During the season, he also received a four-game suspension for delivering a blind-side punch to Ian Laperrière. Brashear stated that he hit Laperrière in retaliation to Laperrière punching Brashear's teammate Gino Odjick from behind. The 1998–99 season marked the only time in his career which he played in all 82 games, again leading the Canucks in penalty minutes and finishing eighth in the NHL. In the 1999–2000 season, Brashear set a career-high in goals with 11, but the season was marred by one of the most published incidents of excessive violence in the modern era of hockey.

Brashear has represented the United States on two separate occasions. He made his international debut at the 1997 World Championship, where he registered two goals and five points in eight games, helping the Americans to a sixth-place finish. He later noted that he was surprised by the invitation, but felt that it gave him an opportunity to show he could play other roles besides being an enforcer. He played for the U.S. again the following year at the World Championship, playing in six games and accumulating ten penalty minutes as the Americans finished in 12th place.

Brashear was signed as a free agent by the Montreal Canadiens in 1992. He spent parts of three seasons with their American Hockey League (AHL) affiliate, the Fredericton Canadiens, before becoming a regular with Montreal at the NHL level. During the 1993–94 AHL season, he registered professional career highs of 38 goals and 66 points, along with 250 Penalty Minutes (PIMs) in 62 games. His 38 goals tied him for the team lead and the 250 PIMs led Fredericton. Brashear made his NHL debut on November 15, 1993, against the Ottawa Senators. He registered an assist in the contest, his first career NHL point. Two days later, he scored his first NHL goal in a game against the Edmonton Oilers. After playing parts of four seasons with the Canadiens, his time in Montreal ended following a heated verbal exchange with Head Coach Mario Tremblay during a team practice on November 9, 1996. Four days later, Brashear was traded to the Vancouver Canucks in exchange for Jassen Cullimore. Brashear finished the year with 13 points and 245 PIMs, seventh-highest in the NHL.

At the age of eight, Brashear moved to Val-Bélair, Quebec, and settled into a new foster home. Once there, he began playing hockey with his new siblings. To help pay for hockey, Brashear sold baked bread and garbage bags door-to-door, and later became a paper boy. He played in the 1984, 1985 and 1986 Quebec International Pee-Wee Hockey Tournaments with three separate minor ice hockey teams from Quebec City.

Donald Maynard Brashear (born January 7, 1972) is a Canadian-American former professional ice hockey player who played for five organizations in the National Hockey League (NHL), in which he played the role of enforcer. He was among the NHL leaders in penalty minutes for six seasons, while ranking 15th all-time in penalty minutes. He remains the Vancouver Canucks all-time single season leader in penalty minutes, which he set in the 1997–98 season. He was involved in one of the most publicized incidents of on-ice violence in NHL history during the 1999–2000 season, when he was slashed in the head by Marty McSorley.