"My pitch to him was, 'You can still skate, we've evaluated that. You're going to be able to skate when you're 45 and 50,' " Holland told NHL.com. "It's emotionally getting engaged that I'm going to another season, a new team, a new challenge, and I have to get myself ready. I thought the longer he waited into August the less time he gave himself to be mentally prepared for the season."
Holland's advice worked. A few days later he received a phone call from Modano's agent, Mike Liut, who said he had received the green light from his client to work out the deal. Modano will reportedly make a base salary of $1.25 million to be the Wings' third-line center, and the contract also includes a bonus package.
Modano played 20 seasons in the Dallas Stars organization, including four in Minnesota, and he's the NHL's all-time leading American-born scorer with 1,359 points in 1,459 games. Modano is 23rd all-time in points, 24th in goals (557) and 29th in assists (802).
"He has made a decision that he still wanted to play hockey so he still has that passion. One option for him was obviously to call it a career and it's a Hall of Fame career," Holland said. "And, he's coming to Detroit and it's somebody else's team. I think that's a good thing. It's somebody else's responsibility to drive the team. In the 1990s and early 2000s, it was his job to drive the Dallas Stars."
Holland had been working on this Modano deal since early July, when the free agency signing period opened. It started with a few phone calls to Liut and it escalated a week later to Modano coming to Detroit and spending the day with Holland and coach Mike Babcock.
They drove Modano, a Livonia, Mich. native, around the upper west side neighborhoods where most of the Red Wings' players live. They told him what the Red Wings were all about and why they were pursuing him. They sat in a suburban restaurant for two hours and talked about line combinations. They brought him to meet Red Wings' owners Mike and Marian Ilitch, and they attended a Detroit Tigers game.
"Mike Babcock and I did most of the talking, and Mike has a gift of gab and I have a gift of gab, so there probably wasn't much time for Mike Modano to talk," Holland said.
Holland said he didn't contact Modano after he left, choosing instead to give him time and space to think about his options.
"You've got a guy that has played with one organization for 20 years, and all of a sudden you're making a decision to go play somewhere else," Holland said. "I thought he needed time to sort things out emotionally in his own mind to prepare himself to play."
Roughly 10 days later, Holland received a text message from Modano.
"It got me excited because he's obviously thinking of us," Holland said.
Holland has heard the critics talking about Modano's age. He chooses to tune them out.
"I don't really look at the birth certificate," he said. "I try to gauge the player on the ice. Mike Modano was a superstar in his day and his skills are probably diminished, but the reason that superstars can play in their late 30s and early 40s and still be effective is they were so much better than everybody else when they were 28 to 30 that their skills are good enough to come out if you get them excited and you put them in an environment that allows them to be successful.
"Igor Larionov played great for us at the age of 40 (and won a Stanley Cup), and we're hoping the same with Mike Modano."
Modano is the Wings' second 40-year-old (Nicklas Lidstrom) and the seventh player on the team who is 35 or older (Todd Bertuzzi, Brian Rafalski, Chris Osgood, Kris Draper, Tomas Holmstrom). But Holland said other than the defensive pair of Lidstrom and Rafalski, who is 36, the rest of the guys will be asked to be support players.
Modano will start camp centering the third line between Cleary and Hudler. Holland said if they don't develop chemistry, Modano could switch with Filppula and play between Franzen and Bertuzzi. Filppula has played with Hudler and Cleary in the past.
"I see (Modano) maybe playing 14 to 16 minutes a night guy and probably in his prime he played 18 to 22," Holland said. "There are going to be nights when he's probably feeling good and he's dancing, and Babcock is going to get him out there more. There will be other nights when you can tell he just doesn't have it and somebody else will play more."
If this works out with Modano, Holland sees no reason why he wouldn't play a second season in Detroit. Modano can sign an extension after Jan. 1, but Holland doesn't see anything happening until they can assess the full season.
"If he's playing outstanding and he's happy, I don't see why he'd want to leave," Holland said. "We've just got to go play. It all sounds good."
Follow Dan Rosen on Twitter at: @drosennhl