His future as executive director hangs in the balance heading into a Sunday night conference call with the NHLPA's executive board - made up of the 30 player representatives and the six-member interim executive committee.
People with knowledge of the situation believe he'll probably be out as executive director, if not Sunday then certainly in the near future.
Saskin's bleak outlook pales in comparison to the optimism that greeted his arrival as executive director on July 28, 2005. At the time, the majority of players believed he was the right man for the job, a long-time union lawyer who would bring a softer, more diplomatic approach in dealings with the NHL, replacing the abrasive-yet-brilliant Bob Goodenow.
The common refrain at the time, coming out of the lockout, was that it was a new era in the NHL, with the league and players needing to work together to grow the game. And Saskin was seen as the man for the job.
"If you talk about Ted, I think he's a superstar, somebody that I really discovered this year while negotiating," former NHLer Vincent Damphousse, then a member of the NHLPA's executive committee, said on July 28, 2005, after Goodenow was pushed out and Saskin brought in.
"His relations that he had with all the partners, with the PA, he negotiates all the marketing and licensing deals, but he's got great relations with the league as well. He's perfect for the job."
Except Saskin, many believe, made a critical error in judgment that has dogged him ever since. Instead of taking over on an interim basis, Saskin immediately took over Goodenow's job permanently after negotiating a five-year contract with former players' president Trevor Linden.
Taking over on an interim basis would have given the players time to put together a search committee and interview other potential candidates for the job. The players also needed time to catch their breath, having just signed off on a salary cap after spending years saying they would never do so.
But there was no search committee (not that the NHLPA constitution states there must be one). Saskin took over the same day Goodenow was gone, and that's when then-executive committee member Trent Klatt felt uneasy with the quick transition and began to voice his dissent. Detroit Red Wings defenceman Chris Chelios joined forces with Klatt and, while they had very little support in the early going, their persistence over the last 18 months led to an internal review currently being conducted by Toronto lawyer Sheila Block.
Then there was this week's explosive developments, allegations that Saskin ordered the monitoring of NHLPA player e-mails - which he denied to CP on Thursday. The e-mail system the players use is administered by the union.
It might be a different story today if Saskin had decided to hold back in the summer of 2005, leaving room for a search for other candidates to materialize. It would have been a shock had Saskin not been hired full-time at the end of that process.
At the time, the overall sentiment was that Saskin was the obvious choice to replace Goodenow. He was the architect of the new CBA alongside his counterpart Bill Daly, the NHL's deputy commissioner. Saskin knew the deal inside out and was seen by many as being more qualified than anyone to lead the NHLPA in the new era.
Like Daly, Saskin became the face of the NHL lockout, expertly arguing the union's case in the media and displaying the kind of moxie in front of the camera that his predecessor did not show. He emerged from the lockout as a star and the future looked bright.
How times changed quickly.
Not much is really known about Saskin. The 48-year-old Montreal native is a family man but intensely private when it comes to his personal life. He lives in Toronto with his wife and four kids.
Saskin was Goodenow's longtime lieutenant. He joined the NHLPA in 1992 and was credited with helping the union increase its revenue in the licensing department. Like Goodenow, Saskin is a lawyer by trade. He graduated from the University of Toronto's faculty of law in 1983, later joining the law firm of Goodman & Goodman (now Goodmans LLP), specializing in licensing and sports litigation. He was made a partner in 1990.