Some general managers left meetings with Gary Greenstin at the NHL draft shaking their heads. Some assumed he would eventually crack and lower the asking price on free agents Mikhail Grabovski and Nikolai Kulemin.
But the veteran agent stood his ground and managed to deliver a pair of four-year contracts from the New York Islanders on Wednesday worth a total of $36.75 million.
It had been a “top priority” for Greenstin to reunite the former Toronto Maple Leafs teammates through free agency. That proved to be no small task in a market where the majority of teams were either feeling the crunch of the salary cap or were unwilling to commit to longer-term deals.
The agent believes he benefited from the NHL’s new five-day window that allowed him to speak with prospective teams. By his count, he met with representatives from 16 different organizations at last weekend’s draft in Philadelphia and during those sessions he made it a priority to cut right to the chase.
"I'll tell you the truth: I had some good experiences and not so good, but I learned a lot for five days," Greenstin told Sportsnet minutes after the new contracts were signed. "Some people looked at me and maybe think 'Who the [heck] are you? What do you ask what money you ask?'
"I have experience, you know?"
As much as Greenstin appreciated the interest he received from so many teams, he wasn't looking to make friends. Grabovski and Kulemin are two of his top priorities -- he also counts Detroit's Pavel Datsyuk as a client -- and the agent was determined to get both players a raise and some security.
"I know maybe some people [were] upset," he said. "I'm not being aggressive. I was listening, OK? And I don't fight, I represent my players; I don't represent somebody else and I love my guys and I know what they will deliver."
Once the free agent market opened at 12 p.m. ET on Tuesday, four teams expressed interest in signing Grabovski and Kulemin as a package. Greenstin wouldn't reveal who they were, but noted that one was a "great team" and another was trying to make roster moves that would free up the cap space needed to get the deals done.
The Islanders weren't one of the organizations that he met with in Philadelphia, but the sides spoke Tuesday and again on Wednesday morning before the contracts were completed.
As a stampede of signings got finalized on the opening day of free agency -- more than $500-million was spent in total -- GMs started circling back to Greenstin to see if he would consider lowering his asking price.
"I was not worried yesterday," he said. "Of course, some teams call me ... and they tried to make me desperate: 'So you go down?' I'd say 'Down? Never down, always up.' ...
"I tried to be friendly, you know what I mean?"
That patience paid off when the Islanders opened their wallet for both of his clients. Grabovski and Kulemin grew close while playing together in Toronto for four seasons -- a run that was broken up last summer when the Leafs used a compliance buyout on Grabovski.
In fact, the players enjoyed their best NHL season while playing on a line together with Clarke MacArthur in 2010-11 and were assured by Islanders coach Jack Capuano that they would be reunited on a unit in Long Island.
Greenstin believes that scenario will allow Kulemin to silence any critics who believe that the Islanders overpaid by giving him a $4.19-million AAV following a nine-goal season.
"You know what? Kulie's a 25-goal scorer -- watch next year, OK?" said Greenstin. "He'll play together with Grabbo, more power-play time next year, watch."
Kulemin turns 28 this summer and represented Russia at the Sochi Olympics. Even though the beefy winger's offensive production has dropped off dramatically since a 30-goal season with the Leafs, he was in demand this summer.
"I know [Evgeni] Malkin really badly would like to play with Kulie, but we couldn't make a deal with Pittsburgh," said Greenstin.
His clients instead landed in Long Island, where they're joining a young team that is desperate to reverse its fortunes with a move to Brooklyn looming in 2015.
The Isles made a play for some higher-profile players on Tuesday before eventually settling on Grabovski and Kulemin.
"To me, free agency is like fishing," GM Garth Snow told Newsday's Arthur Staple. "You put your line in the water and you hope you get some nibbles. We got two big bites today."
They aren't the biggest names to sign deals in free agency this off-season and won't likely make the most significant impact, but finalizing their contracts proved to be no easy task.
Greenstin likes to say that he's "just like a soldier" because he's willing to perform the duties required by his job at any time day or night. He was stretched to his limit over the last week.
A certified NHLPA agent since 1993, he has never engaged in a set of negotiations quite like these ones.
"I had two great guys at one time being UFA," said Greenstin. "And the first time, during this period, where I've been able to talk directly to the teams during the draft. This was an unbelievable experience. ...
"We discussed some numbers with maybe seven or eight teams [on Tuesday]," he added. "I've been not crazy. I've been waiting for today and you see what's happening."