Late in a frenzied first day of free-agent signing, Smyth - the last remaining topflight forward left the New York Islanders on Sunday night for a return trip to the Western Conference.
Islanders general manager Garth Snow, who made retaining Smyth his top priority, got the bad news that Smyth was leaving Long Island shortly before 11 p.m. ET from the forward's agent, Don Meehan.
"It was obviously not what we wanted to hear, but I appreciated the call," Snow said. "Don said we were right in it for Ryan's services until the very end and it was one of the hardest decisions he'd ever been a part of."
The Islanders acquired Smyth from the Edmonton Oilers just minutes before the NHL trade deadline in February. New York gave up two former first-round picks plus this year's No. 1 selection to get him, but couldn't make the big move stick by signing him to a long-term contract.
"Ryan decided it was best for him and his family to sign with Colorado," Snow said. "The Avalanche are very fortunate to have him and we wish Ryan and his family the best. I said when I made the trade to acquire Ryan from Edmonton that it's a deal I'd do over and over again.
"My feelings on the move to bring Ryan Smyth to Long Island have not changed."
Smyth agreed to a five-year deal worth US$31.25 million with the Avalanche, who are looking to quickly rebuild a franchise that missed the playoffs last season for the first time since 1994 - two years before the team relocated to Denver from Quebec.
It capped a very tough day for Snow and the Islanders, who lost several key free agents Sunday - including Smyth and Jason Blake, the team's top two scorers from last season.
All they had to show from a busy first day of free-agent negotiations was a deal with forward Jon Sim, who left the Atlanta Thrashers for a three-year, $3-million deal.
The Avalanche, however, made Smyth their second acquisition of the day after they inked former San Jose defenceman Scott Hannan to a four-year, $18-million contract. That marked the first time Colorado spoiled the Islanders plans Sunday.
"We had a few conversations with Hannan and made him an offer right on par with what he signed for," Snow said. "Scott told us he was flattered by our interest and intrigued by the opportunity to play for (Islanders coach) Ted Nolan, but his first choice was to stay in the West. We weren't surprised when he went to the Avalanche."
Smyth also watched former Buffalo co-captains Chris Drury and Daniel Briere leave the Presidents' Trophy-winning Sabres for big deals with the New York Rangers and Philadelphia Flyers, respectively, before making his move.
Scott Gomez also joined the Rangers on Sunday, leaving the New Jersey Devils for a seven-year deal worth $51.5 million.
Smyth was dealt to the Islanders by the Oilers in a stunning deal at the trade deadline. Known as "Captain Canada" for his experience with his home country's national teams, the Banff, Alta., native was shipped out of Edmonton after spending his first 11-plus NHL seasons there.
He turned down a multi-year offer from the Oilers that would've paid him more than $5 million a season and was traded to the Islanders for former first-round picks Robert Nilsson and Ryan O'Marra. Edmonton took defenceman Alex Plante last weekend with the draft choice they got from New York.
Smyth's departure capped a rough first free-agency opener for Snow, who retired as a player last July to immediately take over as Islanders GM from the fired Neil Smith.
In the opening hours of the signing period Sunday, the Islanders lost leading scorer Blake (Toronto), fellow forward Viktor Kozlov and top defenceman Tom Poti to the Washington Capitals, and another forward, Richard Zednik, to Florida.
Smyth finished second on the club to Blake with 68 points and provided necessary leadership New York needed in its dressing room.
They added Sim, a 30-year-old, grinding right winger who had 17 goals and 12 assists in 77 games with Atlanta last season.
"Jon Sim is an aggressive, hardworking veteran forward with good offensive skills who fits in perfectly with (coach) Ted Nolan's system," Snow said.
In 307 NHL games over eight NHL seasons, the 5-10, 190-pound Sim posted 52 goals and 45 assists.
"I really like Jonathan's game and I believe he's an excellent addition for us," Nolan said. "He's a tenacious player who doesn't take off a shift. He's exactly the kind of player we want for the Islanders."
Blake, the Islanders' leading scorer last season with career highs of 40 goals and 69 points, signed a five-year, $20 million contract with the Maple Leafs. Kozlov, who had a career-best 25 goals and 51 points with New York, turned that into a two-year, $5-million deal with the Capitals. He will team again with Poti, an offensive-minded defenceman who put up 44 points in his only season with the Islanders.
Poti received a four-year, $14-million contract from the Capitals. Zednik, also acquired shortly before the trade deadline, signed a two-year deal worth $3.25 million with the Panthers.
The Islanders also bought out the contract of former captain Alexei Yashin after the season, and were prepared to make Smyth the new captain if they could have convinced him to stay.
Regardless of whom New York signs to replace the lost parts, those players will be in front of goalie Rick DiPietro, who is set to enter the second season of his landmark 15-year contract with the Islanders.