Selected by the Colorado Avalanche with the No. 18 pick in the 2006 NHL Draft, Stewart scored 322 points (160 goals, 162 assists) in 668 NHL games with seven teams from 2008-20, and 11 points (six goals, five assists) in 39 Stanley Cup Playoff games. He also played for Canada at the 2011 IIHF World Championship in Bratislava and Kosice, Slovakia.
"Chris is going to bring tremendous expertise, knowledge in the sport of hockey," Anderson said. "He also has tremendous influence within bigger hockey circles, the NHL and IIHF and we expect that we will be able to use some of that experience and know how that Chris has to be able to present programs that we believe will be worthwhile enough for the two bodies to support us on."
Stewart will join former NHL defenseman Jamie Huscroft behind the Jamaica bench. Huscroft scored 38 points (five goals, 33 assists) in 352 NHL games with seven teams from 1988-2000 and one assist in 21 playoff games.
Anderson said Stewart is already paying dividends in his hockey ambassador role. One of his first acts was to connect the JOIHF with the NHL Players' Association Goals & Dreams fund to apply for a donation of hockey equipment to help grow the game in Jamaica.
The fund is the world's largest grassroots hockey program, providing more than 80,000 children in 34 countries the opportunity to play the sport over the past 21 years through equipment donations. It has donated more than $25 million to help grow the game of hockey.
"I just connected the dots, I know the PA and know they're always looking for things to help out on," Stewart said. "Yeah, they've been speaking and, hopefully, we can build the relationship into something that can materialize into something good."
Jamaica would join Costa Rica as the second Caribbean country to benefit from the Goals & Dreams fund if the JOIHF's application is approved.
Stewart hopes to further assist the effort in Jamaica by being one of five North American coaches at a week-long hockey clinic at the G.C. Foster College of Physical Education and Sport in St. Catherine, Jamaica, which has added the sport to its curriculum.
"We anticipate 25 to 50, even more kids," Caple said. "It would be free of charge. We're going to go through a lot of the basic skills and concepts of hockey that you would on the ice rink."
Jamaica's biggest hurdle to full IIHF membership and Olympic qualification is the lack of a skating rink on the island. Anderson said JOIHF officials hope Stewart's presence and hockey resume will help serve as a selling point in getting one built.
There were reports in 2019 that a Canadian investor was interested in building a rink as part of a resort on the island's north coast and Anderson told Jamaican media the federation has spoken with some private companies about constructing a synthetic ice sheet as a short-term solution.
In the meantime, Stewart is keeping his eyes on the prize that potentially awaits in Coral Springs in October.
"We've gone from the hunter to the hunted. We're the defending champs," he said. "We're the measuring stick, right? So it's no different than Tampa Bay (Lightning) or Chicago (Blackhawks) when they were going through it. Every team is preparing to beat you that night. We're the measuring stick."