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On a recent flight home, I decided to watch Moneyball. It’s one of my favorite sports movies and was probably my 30th viewing, but it has yet to get the least bit stale for me.

The film tells the story of Oakland Athletics GM Billy Beane and his attempts to reinvent the way baseball teams are built during the 2002 season. Interwoven in the story are some of the intricacies that come with life as a general manager in pro sports.

One of my favorite scenes is trade deadline day when Beane is in his office working the phones with assistant Peter Brand. In a six-minute span, the two make eight different calls to four different people. It’s chaos, it’s madness, it’s high-energy. After all, it’s the trade deadline.

Jim Nill knows all about it.

“I think it’s important for people to understand the process,” Nill said. “First of all, when you come out of training camp and start the season, you’ve got a projection of where your team is at. As the season goes on, you start to watch. Do you see some holes in your roster? Are there some injury situations where you might have to adjust something?”

Nill is in the midst of his 11th season as the Stars general manager and has gained a strong grasp on the ins and outs of the process. And as this year’s deadline approaches on Friday at 3 p.m. ET, he’s putting the finishing touches on another extensive exercise.

It all began at the start of 2024 in meetings with scouts.

"We analyze other teams to figure out who’s in the playoffs, who’s going to be a buyer and seller, what they have available, who are the UFAs and all that stuff,” Nill said. “When I come out of those meetings in late January, I start to call other teams. I say, ‘Hey, here’s what my needs are. What are your needs?’ We just kind of talk.”

That talking has gotten Nill places in the past. Last year, he acquired Evgenii Dadonov and Max Domi, and both played valuable roles in the Stars’ postseason run.

In 2019, he pulled off a deal for New York Rangers forward Mats Zuccarello, who became the centerpiece of the Stars’ offense in the Stanley Cup Playoffs.

The 2022-23 Jim Gregory GM of the Year Award winner took a big swing last week and acquired defenseman Chris Tanev from Calgary. As the most-pursued defenseman on the trade block, it required a little bit of waiting and feeling out with a team uncertain of its own future.

But that’s all part of the game.

“By that last week or 10 days, things start to get pretty serious which direction you’re going,” Nill said.

That has to be a pretty crazy process, right?

“It can get chaotic,” Nill said. “The last two days, you have to decide if you’re in or out. Are the asking prices going up? It’s supply and demand. Are there not a lot of players available at the position you need? Maybe there’s three or four teams looking for defensemen, or six or seven looking for a forward, or two or three looking for a goalie. You don’t know.”

Not only are you juggling racing against other teams and putting together the best package, but there’s also the salary cap’s daily impact.

In order to make the Tanev deal work, the Stars had to weave in the New Jersey Devils to pay for a chunk of his salary. That leads to more phone calls, and you guessed it, more stress.

“We had to do a retention, so we had to find a team to do it,” Nill said. “You’re only allowed three retentions, and you might have 12 teams that already used up their retention. Now your numbers are limited. That’s probably the most stressful part of it. You might have a deal done for the player, but until you can get another team involved to do a retention and fit it under the cap, it doesn’t matter.”

But in those times of stress, it’s nice for Nill to know he has a great team that he’s built a strong and trusting bond with during his time as GM. It’s truly a team effort to put the pieces in place.

“I have an unbelievable staff,” Nill emphasized. “Mark [Janko] handles the cap side, Scott White and Rich Peverley are handling the player personnel. I’m talking to Joe McDonnell on the amateur side saying, ‘Hey, what’s the draft like this year? If I give up a second-round pick, are we going to lose some good players? What’s the value of a first-round pick this year?’ We’re bringing that all together.”

As the day approaches, every team has to decide whether they are a buyer or seller. Are you going to bolster your lineup and make a run at the Cup? Or are you better suited to sell some of your assets in exchange for prospects and draft picks?

Nill has been on both sides. In his times as a seller, he’s found a way to strike gold. In 2015, he traded Erik Cole to Detroit for Mattias Janmark (a prospect at the time) and a second-round draft pick that turned into Roope Hintz. In 2017, he dealt Patrick Eaves to Anaheim for a conditional second-round pick that eventually turned into a first spent on Jake Oettinger.

“I would say there’s more pressure as a seller,” Nill said. “You’ve got an asset, you know where your team is at and that you won’t have a long run or you’re already out of the playoffs. You get a pretty good feel for the market, and there’s nothing worse than when you know the market is tight, you’re up against the clock and haven’t moved that player or asset yet. That’s stressful because you’re at the whim of the other team. They have to say, ‘Yes, we want to do this.’ You’re sitting there selling and selling and doing all that you can do.”

Now of course, making moves comes with a price. Nothing is free, after all. That price often involves trading away players already rooted in the organization.

Nill knows that it’s a terrible feeling, but as a former NHL player that was traded multiple times, he believes it has helped him with handling those situations as a GM.

“I remember the first time I was traded, I was devastated,” Nill said. “I gave my whole heart and soul to the St. Louis Blues. I was drafted by the Blues, was playing for them and, all of a sudden, you get the phone call and you’ve been traded. You still have to do your job, and my job is to make the Dallas Stars better. But you need to understand that there’s a personal side to it, too. They’ve got families, the kids are in school, their wife might be expecting. Those things come into play.”

In addition to tough choices, there’s also the extensive homework that must be done on new acquisitions. Will they fit into the dressing room and form quick bonds? Are there any red flags below the surface? That requires a meticulous level of balance and research.

But for Nill, a strong dressing room can conquer almost any shortfall. That’s why he goes into every deal with the desire to further establish those roots.

“If you’re going to win, you have to have that environment,” Nill said. “You’re going to go through tough times. If you have a fractured room, those fractures are going to become craters. You have to have the right people in place. I’ve got a great coaching staff, great players and leadership.

"The leadership in the room is so important. Part of that, too, is that you want it to continue. The leadership that Jamie Benn, Joe Pavelski, and Ryan Suter bring and they’re sitting next to Wyatt Johnston and Thomas Harley and are passing the torch down. If you want long-term success, you have to have that.”

All of this combines to form the trade deadline dance. It’s scouting and meetings. It’s phone calls and changing offers. It’s tough decisions in hopes of positioning your team for a run at history. There’s a whole lot of teetering uncertainty.

It’s what Nill has come to expect. And as he prepares for the final few hours of what has been a quieter than usual deadline period, he knows that the storm could ramp up at any moment.

“My sense is that a lot of teams over the last three or four years have done a lot,” Nill said. “And when I talked about assets, you get to a point where you either don’t have assets or can’t give any more up. The teams that feel they have a real good chance are going to do whatever they can and the teams just below that are going to say, ‘You know what? I think it’s chill time and let’s see what happens."

This story was not subject to the approval of the National Hockey League or Dallas Stars Hockey Club.

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