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It’s never easy saying good-bye to long-time friends. Ryan Miller has been doing a lot of that the past couple of seasons. It hasn’t gotten any easier.

Another one of his best friends, and member of the Buffalo Sabres’ core that was supposed to lead the blue and gold to the Stanley Cup, has left Hockey Heaven. The only thing surprising about Thomas Vanek’s departure via trade to the New York Islanders on Sunday night though was in its timing – not that it happened.

Miller has already said farewell to Paul Gaustad, Derek Roy, Jason Pominville and Jochen Hecht, ex-teammates who left the organization either via trade or retirement. It’s still been a rough couple of days for the Sabres’ starting netminder.

“It’s hard to watch all of them go,” Miller said Monday night after the Sabres’ 4-3 loss to the Dallas Stars in First Niagara Center. “It’s been difficult each time. All these guys have been close friends and great hockey players.”

Miller had formed a bond built through competitiveness with Vanek ever since they became teammates with the Sabres’ minor-league affiliate in Rochester during the 2004-05 season. Both have been lineup regulars with Buffalo ever since the start of the 2005-06 season. Vanek picked up an assist in his NHL debut Oct. 5, 2005 against the Islanders and Miller earned the win in goal.

“It was fun to compete against him in practice,” said Miller, who along with Drew Stafford are the remaining survivors of the core group the Sabres had hoped would turn into a Stanley Cup contender by now after placing great expectations on them five years ago. “It’s just going to be another chapter for him and it’ll be something different for me too. He’s a heck of a scorer and heck of a player.”

Vanek was one of the best in Sabres history as he ranks fifth all-time in goals (254) and 10th in points (497).

He played in 598 games with the organization that drafted him fifth overall in 2003.

Like Miller, Vanek will be an unrestricted free agent after the season. Vanek made it clear last season he did not want to be part of a rebuild.

He got his wish Sunday night when the struggling Sabres shipped the left winger to the New York Islanders in exchange for left winger and three-time 30-goal scorer Matt Moulson, who scored twice in his Buffalo debut, and will also be an unrestricted free agent in July. The Sabres also collected the Islanders’ 2014 first-round draft pick and a second-round selection in 2015.

Vanek goes to a team that features superstar center John Tavares and is clearly on the rise coming off a playoff appearance last season. The Sabres have missed the postseason each of the past two seasons (soon to be three) and four of the past six (soon to be five of seven).

While Miller seemed to be having a tough time seeing someone else leave, his teammates weren’t too shocked once they learned of the Vanek deal because they knew of his desire to play for a contender.

“It’s tough to see a friend go but at the same time it was expected,” said forward Tyler Ennis.

“It feels weird not having him here,” Vanek’s former center Cody Hodgson said. “He was our captain, a good friend and a leader.”

One thing that likely caught players off guard, in regards to the deal, is that during General Manager Darcy Regier’s tenure the Sabres have made trades either during the offseason or near the trade deadline, but not during the first month of the season.

“The timing was quicker than people would have thought,” Sabres coach Ron Rolston said.

The Sabres were willing to make him the NHL’s highest paid player, a source told The News, but Vanek has plenty of money (part of the seven-year, $50 million offer sheet he signed with Edmonton that the Sabres matched in the summer of 2007).

He doesn’t have a Stanley Cup ring, something he would not have been able to compete for anytime soon in Buffalo.

“We wish him the best in terms of his goals,” Rolston said.

Steve Ott will now be the Sabres’ full-time captain.

email: mrodriguez@buffnews.com