The two former players have won a combined total of nine Stanley Cups and played a total of 1,600-plus games each. Both have been inducted into the Hockey Hall of Fame and named to the "100 Greatest NHL Players" list by the NHL in 2017.
Even though they have not faced each other often, the veteran defenseman believes that he and Messier balance each other out in the studio with their different personalities.
"It's crazy that I never really got to play against Messi or Wayne [Gretzky] with all those years in the playoffs," Chelios said. "[He was] a great leader and it would have been awesome to play a season with him. It never happened but now here we are on a team together. I think together Mess is serious, real serious. Now I get why guys followed him. It's been great."
The former forward compared his winning 1983-90 Edmonton Oilers team to the 2010-15 Chicago Blackhawks that won three Stanley Cups. The only difference of the two teams he pointed out was having Wayne Gretzky.
Messier noted the strong nucleus that the Blackhawks organization built around players like Jonathan Toews and Patrick Kane. With the challenge of the salary cap, the team still found the right fit of players to help create a strong, winning franchise during their Stanley Cup years.
"When you start with two players like Toews and Kane that is an amazing pillar to work from and to start a team from," Messier said. "They were clutch in every situation and had three Stanley Cups in the salary cap era, which is pretty strong. My hat is off to them and the organization for getting that team together and keeping the core together."
As the Blackhawks look towards the future of prospects within their pipeline, Messier describes the challenges this could bring while trying to keep veteran players such as Kane and Toews as they continue to look for success and a fight to the playoffs.
"I don't think there's any easy way to end the tenure for those two here in Chicago for the team and for themselves," Messier said. "I think everybody and every hockey fan would say they would want to see Toews and Kane in the playoffs and see them on a competitive team and try to win another Stanley Cup."
Chelios understands the challenges facing Kane and Toews but states that they are in a more emotional position compared to his exit. When the former Blackhawk left in 1999, he pointed out that he was still wondering if he could ever capture the Stanley Cup whereas the dynamic duo captured three.
He stated that if he had similar success with the team, he would also know the difficulty of leaving the organization.
"As much as it was great for me to play in my hometown, I never had that success of winning the Cup or fortunate to win that Cup," Chelios said. "I was a little bit in the same boat [as Kane and Toews] but if I had that success then it would had been a lot tougher to leave Chicago."
