Chelios has been in the playoffs with Detroit every season since Chicago traded him there in 1999 and won a Stanley Cup with them in 2002 at the age of 40. Messier missed the post-season seven straight years before retiring following the 2003-04 season at the age of 43.
"I think it makes a huge difference to continue on playing when you are successful," he said Thursday from his home in Hilton Head, S.C. "It can get real old after you've played 20-some years to not to be winning during the regular season and playing in the playoffs.
"There's winning and misery and there was a lot of misery in my last few years.
"I think things would have been different for myself if we were winning 50 games a year and having a good time doing it.
"It would have made my decision harder to retire."
Work ethic, good genes and what's happening on the home front also contribute to a player's longevity in the game, Messier said. He isn't surprised to see Chelios in his 22nd NHL post-season at the age of 45.
"He's done what he's had to do to condition himself to continue to play," said Messier. "His kids are grown up and a little bit older which allows him the freedom to continue to play. He loves the game and he's in a situation where they are successful. You look at the year they had again, an unbelievable season.
"They're still winning, he's still effective and he's loving it. When you add all those up, sure I can believe it."
Messier's career spanned 25 years and included six Stanley Cups, but missing the playoffs so many years in a row eventually sapped his will to play. Adding to his family in his early 40s also contributed to Messier's decision to call it quits.
"I chose to start a family later in my career, almost towards the end of my career and it changed everything for me," said the 46-year-old Messier.
"I wanted to be home more and when your priorities change like that, it's a good indication that perhaps things have to change in your life and for me, it was time to retire."
Messier and partner Kim Clark had son Douglas in Messier's final season and now have daughter Jacklyn as well. Messier also has a 19-year-old son Lyon from a previous relationship.
While Messier says he misses playing, particularly at this time of year, he doesn't want to be back out on the ice. He plans to return to the NHL again as a general manager.
"I could see where the competition is there and where it would be fun to try and do that and be part of a team that's won a championship from a different level," he said.
Messier won five Stanley Cups with the Edmonton Oilers, who retired his No. 11 in February, and also led the Rangers to their first Stanley Cup in 54 years in 1994.
So he's going with his heart, not his head, when he picks the Rangers to win the title this year, even though they are the underdog in their Eastern Conference semifinal against the Buffalo Sabres.
"They came into the playoffs as one of the hottest teams there," Messier said. "They've got an excellent goaltender and arguably the best player in the league.
"They've earned the right to play in the playoffs this year with an unbelievable stretch of games towards the end of the season. Anybody with a goaltender as good as they've got has a chance."