Even with those frustrating setbacks, both Reddick and Brathwaite are optimistic about the future of the game and its diversity.
They look at Quinton Byfield of the Los Angeles Kings - the second overall pick of the Los Angeles Kings in 2020 - and Darnell Nurse - a big name defenceman for the Edmonton Oilers - as just two examples of the players kids can look up to.
And that short list doesn't even include P.K. Subban, Anthony Duclair, Mathieu Joseph, K'Andre Miller, or Matt Dumba.
"I feel that hockey is a more diverse sport right now," said Brathwaite. "You're seeing more girls playing, you're seeing more different backgrounds playing. I feel that hockey is getting better, it's not where it has to be, but we're getting better at that."
Just like when Reddick was with his dad, hearing him talk about O'Ree playing for the Bruins, he looks at the black representation in the game as a positive thing for the kids he works with every day.
"I just think the more people they see of their race, or their colour, or their ethnicity, the easier it is for them to say 'Hey I want to do this mom' or 'Hey I want to do this dad,'" said Reddick. "It's a big help when you get to see different people in different realms step up and make the National Hockey League become big figures to these kids. It's a great opportunity to see those kinds of people and they're good character people."
The same could be said of Reddick and Brathwaite, who continue to promote the game everywhere they go.
Brathwaite even got into a game last season, when at the age of 48 he suited up as the backup goaltender to Henderson's starter - Jiri Patera - with Logan Thompson unavailable.
"I was pretty comfortable because most of my career was on the bench, so that's where I was - on the bench," he laughed. "The guys were very supportive. The other team, San Diego, was very supportive as well. It was nice just to be back in the dressing room and back with the guys again."
Perhaps it reminded him of his time with the Manitoba Moose, where he accomplished another career milestone - scoring a goal.
"I actually just got a card yesterday with a picture of me scoring a goal when I was with the Moose," said Brathwaite. "I don't know if you guys sent that or not, but it's a little ironic that it's all coming back full circle."
No matter where they go, Brathwaite and Reddick's memories of Winnipeg stay with them.
"I played five years there and enjoyed every day of it," said Reddick. "Great people and the whole city was awesome. I ended up living there for eight years."