Longtime NHL players have nearly endless options once they retire from the pro game.

Many former players transition into broadcasting or coaching roles. Sometimes, they join the front office of an NHL team and work their way upward.

That said, some paths stand out for being different or quite impressive. Here is a short list of six former NHL players who have taken on an interesting path beyond their careers.

Zdeno Chara

During his time in the NHL from 1997 to 2022, Zdeno Chara was one of the most feared defensemen in the league. At 6-foot-9, the Slovakian mutant dominated the ice from the back end.

However, when he retired from the NHL after the 2021-22 season, he continued his ways of being a physical force, but not on the ice. 

Chara has participated in a number of marathons following his retirement. He had run in multiple Boston marathons, the London marathon (six days after his second Boston marathon), and the New York marathon.

Most recently, the 48-year-old completed the Czech Republic Iron Man triathlon. The challenge consisted of a 1.2-mile swim, a 56-mile bike and a 13.1-mile run. He completed the triathlon in an impressive 4:56:47.

Joe Pavelski

Joe Pavelski, who retired from the NHL just last summer, wasted no time seeking glory in the next chapter of his life.

In mid-July, Pavelski participated in the American Century Championship, a celebrity golf tournament consisting of several athletes, actors, comedians and more. This was Pavelski’s ninth attempt at the championship in Edgewood Tahoe Resort, Nev.

The 41-year-old came close to winning the tournament several times in previous years, including a runner-up finish in 2024.

However, he finally took home the American Century Championship title, and in dramatic fashion. On the 18th hole, the former San Jose Sharks and Dallas Stars center connected on a walk-off eagle to win the tournament.

JOE PAVELSKI. WALK-OFF EAGLE TO WIN IT. 🦅 pic.twitter.com/Clze1Z375h

— NBC Sports (@NBCSports) July 13, 2025

Chris Phillips

Chris Phillips holds the record for most games played by an Ottawa Senator. The former defenseman played 17 seasons for the Sens, but in the meantime, he opened up a brewery and restaurant.

In 2012, Big Rig Brewery was born and co-owned by Phillips. The Brewery is named after him – Big Rig was his nickname during his playing career.

Just one year later, Big Rig was recognized as the New Brewery of the Year in Ontario, awarded by the Ontario Brewing Awards.

In 2014, his brewery and restaurant became the fastest-growing microbrewery in Ottawa, according to the Ottawa Citizen. 

In addition to the quick success and demand for Big Rig beers, the company has an impressive resume when it comes to the quality of its product. In the 2016 Ontario Brewing Awards, Big Rig took home five medals, including four gold medals in the Hefeweizen, Dark IPA, Scotch Ale and Doppelbock categories.

Ken Dryden

Once a legendary goaltender for the Montreal Canadiens between 1970 and 1979, Ken Dryden took his talents to the House of Commons and became a member of Parliament, elected in 2004.

The six-time Stanley Cup champion was a member of several committees, including National Defence, Library of Parliament, Health, Human Resources, Social Development and the Status of Persons with Disabilities. Furthermore, he was a Minister of Social Development from 2004 to 2006.

In 2013, Dryden was made an officer of the Order of Canada, the highest level of distinction in the Canadian Honours System. He earned this status for his contributions to Canadian life as a hockey player, lawyer and public servant.

Stu Grimson

After 14 seasons in the NHL across seven different teams, Stu Grimson is spending his retirement as a lawyer. 

Grimson, known as ‘The Grim Reaper,’ has accumulated 2,113 penalty minutes during his NHL career. Following his retirement in 2003, the former enforcer returned to school, completing his undergraduate studies in economics and earning his law degree at the University of Memphis.

Since then, he’s worked as a labor lawyer for the NHLPA’s union and later became a defense attorney at Kay Griffin PLLC.

Now, Grimson is the vice president of business development for the company ‘ThirdHome’ and is a member of its corporate counsel.

In addition, he is a hockey analyst for the NHL Network, and has a biography book published called The Grim Reaper: The Life and Career of a Reluctant Warrior.

Randy Gregg

Randy Gregg, a former defenseman for the Edmonton Oilers and the Vancouver Canucks from 1982 to 1992, has transitioned into a physician. 

Gregg, now known as Dr. Gregg, is a primary care physician at the Lifemark Sport Institute in Edmonton. The Canadian-based company offers multidisciplinary rehabilitation services. 

Dr. Gregg specializes in evaluating sports-related injuries, specifically musculoskeletal injuries and has done so for over 25 years.

The former D-man played 474 games in the NHL, scoring 193 points while contributing to five Stanley Cup victories as a member of the Oilers.

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