Jim Nill didn’t hesitate on the phone when asked about his most memorable trade deadline during his 15 years serving as general manager Ken Holland’s assistant with the Detroit Red Wings.

It was a month prior to the March 23, 1999 deadline when Chicago Blackhawks GM Bob Murray told Holland there was no chance he would deal 37-year-old defenceman Chris Chelios.

Detroit hadn’t made a trade with its arch rivals in 33 years, and it didn’t appear it would happen this time, either. That is, until Murray called Holland a day before the deadline and asked if there was still interest in Chelios, who was seeking a two-year contract extension before he would waive his no-trade clause.

Holland retired for the night unsure if talks would lead to a trade “and then things really started to move about 10, 11 in the morning,” he told Michigan’s MLive.com last year, recalling his talks with Murray.

Three hours after asking Red Wings owners Mike and Marian Ilitch if they were comfortable extending Chelios’s contract for two years at $5.5 million US per season, the blue-liner was a Red Wing. In return, Chicago received promising defenceman Anders Eriksson and two first-round draft picks, which became defenceman Steve McCarthy (in 1999) and goalie Adam Munro (in 2001).

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Nill, left, worked for 15 years as an assistant to Red Wings GM Ken Holland, right, learning about patience and when it feels right to make a deal at the NHL trade deadline. (Bruce Bennett/Getty Images)

“First of all, whoever thought [Chelios] would leave Chicago, his hometown? At the time, we thought it was about a two-year trade,” Nill, now preparing for his first trade deadline as an NHL GM with Dallas, told CBCSports.ca last week. “We thought [his NHL days were] pretty well done.

“He ended up playing another [nine-plus seasons]. The impact he had in the dressing room and with our younger players, there was so much that went into [our thinking] about acquiring Chris Chelios, the intangibles that [fans] wouldn’t understand.

“[His influence as a leader] in the dressing room, how he prepares [for seasons and games], how professional he is and how it’s all about winning,” Nill added. “It’s those little things that make it one of the largest trades we made at that time.”

Not shooting for Stars?

Nill, 55, isn’t expected to make a move of that magnitude in his first go-around in Dallas, which occupied the eighth and final playoff spot in the Western Conference entering play Monday.

The Stars, who could ship out impending unrestricted free-agent forwards Ray Whitney or Vern Fiddler, are seven points behind No. 7 Minnesota with a game in hand.

Nashville, at No. 12, is only four points in arrears of Dallas, which has a game in hand.

“It’s an unknown time of the year,” Nill, a native of Hanna, Alta., said. “If some teams [make certain moves], other teams are going to react to it. And if it’s different teams that do something, teams won’t react.

“The salary cap has changed [trade possibilities] too. The other part that has changed a lot is the value of [draft] picks. It’s a young man’s game now, you have to have young guys coming up [through your minor league system].”

The father of three also talked to CBCSports.ca about how his trade-deadline role has changed since leaving Detroit, what he learned about the deadline working with Holland and whether he’s open to rental players in Dallas or only those with term left on their contracts.

1. What is the biggest difference in your role now leading up to the trade deadline than when you were in Detroit?

I was very fortunate in Detroit. [GM] Kenny [Holland] gave me a lot of responsibility, so I was right there in the pits with him. Actually the whole staff was.

You’re going to sit down with your scouting staff and get them organized. If you’re going to decide to [make a trade] you have to make a decision and you’re going to have three guys in your room want to do it and three not want to do it. Somebody has to make that final call and the general manager has to do that.

The good thing is, much like in Detroit, in Dallas I’m surrounded with a great staff. I’ve got a lot of experience with the people here so we’re ready for any decision we have to make.

2. In the final hour before Wednesday’s 3 p.m. ET deadline, what will you be able to glean from your experience working with Red Wings GM Ken Holland?

We’ve all got these grand ideas of what [we want to accomplish]. We’ve got the list of the players we’d like to get and trades we want to make and it all makes sense to us. Trouble is, you’re dealing with 29 other teams that have the same ideas and want to do the opposite of what you want to do.

A lot of these decisions are going to come down to the last half-hour or 15 minutes before the trade deadline. You’ve just got to be prepared to make that decision and make the right call at the right time.

3. Are there any lasting impressions from working in Detroit that have prepared you for this trade deadline?

Patience is very important. It’s [either] the right time for your team [to make a trade] or it’s not. It’s a gut feeling.

The biggest thing is being prepared. But you can be prepared and all of a sudden the night before the trade deadline you play a game and you might get three injuries. That may change the way you look at a trade deadline. You can’t be giving up a first-round picking knowing that if [you] don’t make the playoffs, this is a top-10 [overall] pick.

4. How do your conversations differ with Holland now that you have the same job title with different organizations?

It is different now [talking trades with Holland]. We both have to protect our interests. It is a different dynamic but we’re professional enough to know how to deal with those situations.

We make our regular calls to each other. A lot of times it’s just to call and talk about family and what’s going on with the team. And we’ve made our professional calls where I say I’ve got an idea and what do you think.

We were together a long, long time. It goes back to our junior years [in the mid-1970s with Medicine Hat of the Western Canada Hockey League]. It’s been a great connection for both of us.

5. With so many teams battling for the eighth and final playoff spot in the NHL’s Western Conference, are you open to acquiring rental players as well as those with term left on their contract?

If it’s a deal that’s going to help us now and help us two or three years down the road … we’ll do it. As far as a rental, or short-term [contract], I don’t think we need that. We’ve got some good depth in the minor leagues. Just to add somebody and you give up a second-round pick for someone that’s just going to be here for six weeks, I don’t see us doing that.