McMillan jokes that he has no idea why Lemieux would go to him with that question, but it shows just how much the Penguins' Hall of Fame owner and legend respects his opinion.
"I think Mario always knew Tom had his back, as we all did," said Morehouse, the Penguins' president and CEO. "And I think Tom understood Mario better than anyone else."
So that night, McMillan went back and forth with Lemieux, helping him come up with the wording, format and timing for the famous text that the team received the following morning - and the rest was history.
McMillan's name was later inscribed on Lord Stanley's silver chalice, the first of three that the Penguins would capture over the next nine years.
"And were it not for Tom, this franchise wouldn't have those three Cups behind us," Morehouse said. "I can tell you that they would not be there if not for Tom McMillan."
Whether it was hockey decisions or business decisions, McMillan was involved in virtually all major decisions relating to the Penguins. Everybody within the organization - at all levels, but especially at the top with Lemieux and Morehouse - valued his input.
"He's someone I leaned on a lot," said Morehouse, who counted McMillan as his partner and 'go-to guy' professionally since the moment he joined the Penguins back in 2004 as a consultant on the new arena project.
"He helped me as I became an executive with the Penguins. He helped me navigate through a lot of tough times. We've had some crazy things happen around here, and Tom's always been in the red-hot center of them all."
As an excellent communicator with remarkable intelligence and judgment, along with a great sense of humor, McMillan provided counsel, guidance and feedback behind the scenes that not only helped the franchise become what it is today - but remain where it is today.
When negotiations with the governor and state, city and county officials on the new arena had reached an impasse, Morehouse and McMillan found themselves in the office on a Saturday. They sat down and wrote a letter that would have burned all of their bridges, and resulted in the Penguins leaving Pittsburgh for good.
"It was brilliant and very well-written, as most things Tom wrote were," Morehouse said. "But there was no way we could come back from this letter."
Despite their emotional investment in the fate of the franchise, as both men are from Pittsburgh - McMillan grew up in Bellevue, while Morehouse is a Beechview native - they had the good sense to look at each other, print it, and put it in a drawer until the following day instead of putting it in the mail.
"I went back on Sunday and said, wow, are we lucky we didn't send this letter," Morehouse recalled. "So we had the ability to hit hard when we needed to, and Tom had the uncanny ability to say, maybe we shouldn't hit that hard."
Negotiations eventually resumed, and an agreement was reached. Once construction on what eventually became PPG Paints Arena began, there was something unique to the building that was added during the process that only Lemieux, Morehouse…and McMillan know about.
'Unique' is actually a perfect term for McMillan's incredible career that spanned over four decades in sports media and communications, earning the respect and admiration of the entire hockey world for his contributions to the game. He was the Penguins beat reporter for the Pittsburgh Post-Gazette from 1987-92, covering the franchise's first two Stanley Cups, before becoming the club's Vice President of Communications in 1996.
McMillan, 64, retired at the end of June - but thankfully, he is staying involved with the Penguins as a consultant. As Morehouse put it, there is probably more knowledge stored in McMillan's brain about the franchise than any single human in existence.
"He has a career that will probably never be repeated," said Jen Bullano Ridgley, who has taken over for McMillan as the team's Vice President of Communications and counts him as her biggest mentor.
"To be involved in all five Cups in such a degree, whether it's the stories he's written, or the interviews he's done, or the documentaries he's put together - he is a true historian of the Pittsburgh Penguins. You don't get to where he is and have the relationship and the trust from ownership - and especially Mario - without having that history."
McMillan actually traveled to Montreal to cover Lemieux in the spring of 1984, when 'Le Magnifique' was just a teenager playing for Laval of the Quebec Major Junior Hockey League. McMillan has been around ever since, becoming Lemieux's trusted advisor, and close friend.
"From the first day Tom moved from the Post-Gazette to working for the Penguins, he always made sure that me, the team, and the Penguins organization were protected, and he always communicated externally and internally in an honest, positive way," Lemieux said. "Tom may be retired, but he will always be my friend and will still be doing work with the Penguins...plus, we share the same birthday (Oct. 5)."
Looking back, McMillan's future may have been foretold in the phone number for his childhood home - 766-4066.
But before No. 66 arrived in Pittsburgh, McMillan remembers hockey being off the radar in his neighborhood for the first few years of the Penguins' existence. Nobody played, not even in the street, and nobody watched.
Including McMillan himself, until the spring of 1972 - when his friend Tom Payne dragged him "kicking and screaming" to his first Penguins game. McMillan left a changed person, but had no idea hockey would end up being his career. For the time being, he was simply a fan.
McMillan started following the Penguins closely, learned how to skate, and eventually played for his high school team - where an aptitude test showed he would make a great newspaper writer.
So after graduating from Point Park University, McMillan began working in that role for several local papers, covering Pitt football and basketball along with events like the 1984 Olympics.
But before he traveled to Los Angeles for those Games, McMillan made that memorable trip to Quebec to see Lemieux play in person (against a young, unknown goalie named Patrick Roy, no less!) before the Penguins were expected to select him with the first overall pick in the upcoming NHL Draft.
A few years later, McMillan began covering Lemieux and his teammates as the Penguins beat reporter for the Post-Gazette. And he excelled in all aspects of the role.
"Tom was a great beat guy," said WDVE radio personality Mike Prisuta, who bonded with McMillan over their shared love of Bruce Springsteen. "If you were a Penguins fan, you were lucky to have him."
Former Penguins winger Kevin Stevens made his NHL debut the same year McMillan started covering the team alongside Dave Molinari of the Pittsburgh Press, the only two reporters around the team on a regular basis at the time.
Stevens can't say enough about his experience with McMillan, a fantastic interviewer who developed a strong rapport with the players - particularly the stars - and earned their respect for how he went about his business.
"Tommy is a special guy," Stevens said. "My first introduction to reporters was with Tommy and Davey. We were so lucky to have them, especially Tommy. He's such a good guy. After you've been in this game 40 years, you really see how lucky we were. Tommy was great. He knows the game. He was fair. He has a heart. A lot of those guys don't."
With the Post-Gazette's deadlines coming quickly after games, McMillan barely had any time to turn his stories around, and the technology to file them - if you could even call it that - was antiquated. But he managed to thrive under the pressure.
"Tom was a dogged reporter," said Paul Steigerwald, who has known McMillan for over 30 years. "He didn't cut corners just to get something in the paper. He had a competitiveness about him, and that's really important with that job - especially back then - because the Post-Gazette was competing against the Press. He knew that his job was to make sure that he was on top of that beat, and that he got the story before anybody else if he could. He was extremely good at that."
It was also important because back in those days, before the Internet, before social media and before cell phones, if people wanted to find out what had happened in a game, or hear what the players had to say, they relied on McMillan for all of that.
"What he wrote was such a big part of how people felt about our team," Stevens said. "That's how it got out there. People looked in the newspaper. They didn't know us. They knew what they saw on the ice, but what he put out there helped the team grow."
But what ultimately made McMillan so special was his actual writing ability. The content of those articles he filed to the Post-Gazette were truly second-to-none.
"I regard him as the most talented writer who has been on the beat," said Molinari, who is a Hockey Hall of Fame writer in his own right. "He's just exceptionally gifted at putting words together in an informative and entertaining fashion."
And that was regardless of the circumstance. Whether it was a random Tuesday night in November of 1987 or the evening that the Penguins captured their first Stanley Cup in franchise history in May of 1991, McMillan would craft pieces that were well-written, creative and compelling.
"A lot of the value in a guy like Tom McMillan is the fact that he made every day more interesting, because you could pick up the paper and read what he wrote…" Steigerwald began before getting choked up. "I'm getting emotional, but it's like, those are the things that make life fun. The ability to pick up the paper in the morning and drink a cup of coffee and read Tom McMillan's stuff…you couldn't wait to read it.
"At that moment, when you're reading it, it was your world. If you're a hockey fan, you're hanging onto every word."
After McMillan joined the Penguins, he continued to captivate audiences, just without a byline. He helped write so many important speeches for prominent members of the organization over the years, including the one former Penguins general manager Jim Rutherford gave after being inducted into the Hockey Hall of Fame in 2019.
"His door was always open. Tom was always willing to help, always willing to share information when it was necessary," Rutherford said. "When you needed to fact check or something, you'd go to Tom. He helped me with my Hall of Fame speech and just did a terrific job with that. Through that process, there were some funny moments. He had a subtle humor. He always made it so easy to work with him. He was great at his job, and a great person."
In 1992, the newspapers went on strike in Pittsburgh. So McMillan decided to leave the Post-Gazette and become a freelance reporter, so that he could do even more hockey coverage as a member of the independent media.
Over the next few years, McMillan edited a paper called 'The Penguins Report,' wrote columns, and hosted a radio talk show on WTAE - which turned out to be something else he excelled at.
He became one of the best in the city, and was considering a career in the medium until the Penguins approached McMillan in 1996, asking him to run their media relations department. McMillan was reticent at first, but then reconsidered, and ultimately decided to take a chance.
It was certainly a different dynamic with McMillan making the switch from being a journalist to managing the relationship between the media and the team, earning him a few odd looks in rooms that were usually off limits to reporters.
"When I first realized he was working for the Penguins, I was kind of like, you're working on this side now?" Stevens guffawed. "That was great. That was just a good move by the Penguins to grab him, because he's such a good guy, had a great reputation."
McMillan's dual perspective, along with the terrific relationships he had cultivated with his peers in the media over the years, proved to be absolutely invaluable.
McMillan looking on at the 2008 Winter Classic
"I don't know that I ever forgave him for going over to the dark side, because it certainly was a loss to the print medium," Molinari joked. "But he was familiar with the needs of media outlets, information that would be valuable to newspaper reporters. And not only what information we might need, but when it might be most advantageous to us to get it, things like that … just knowing our side of the business gave him a leg up on filling that role for the team."
Especially when it came to some of the crises the Penguins would face in the coming years, like when the team filed for Chapter 11 bankruptcy just over two years after McMillan took over the role.
Because McMillan was arguably the best in the business when it came to covering the team, he knew exactly what reporters were looking for, and in turn, knew exactly what to give them.
But McMillan also knew when he couldn't give the media anything. The most memorable moment in his career was when he had to keep the biggest secret in Pittsburgh.
"I'll never forget sitting in Mario Lemieux's office and having him tell me he's coming back as a player," McMillan said.
And right after that, Lemieux told McMillan he couldn't tell anyone! So much had to be dealt with behind the scenes, like getting all of the proper approvals for an owner to also be a player. They also had to start from scratch with all of their marketing and promotional materials for the season.
But when it was finally time to share the magical news, McMillan was the one who coordinated the release of it. Simply put, McMillan did a tremendous job of bridging the gap between the media and the team, and making sure everybody was taken care of.
"He's always been a consummate pro," said TSN Hockey Insider Bob McKenzie, who has known McMillan since, as he quipped, "Tom had hair and mine wasn't gray."
"I always found Tommy Boy an easy guy to talk to and I was always smarter after those conversations. What I love most about Tom is his sense of humor, just a fun guy to be around. Smart and funny, who knew?"
McMillan giving a tour to 2011 Pittsburgh High School Draft Prospects John Gibson, Barrett Kaib, J.T. Miller, Brandon Saad, and Vincent Trocheck
That's why former Penguins head coach Michel Therrien quickly established a great rapport with McMillan shortly after taking over the team on Dec. 15, 2005.
"As soon as I got to Pittsburgh, we bonded really quickly," Therrien said. "We became friends, and every day, he was with me. I got great memories of working with Tommy, and consider him one of my good friends."
Therrien laughed heartily when thinking back to the night he conducted his famous press conference less than a month into his tenure, delivering a scathing rebuke of his team with memorable lines like "I've never seen a bunch of defensemen soft like this" and "they say they care, but they don't care."
It may have seemed like the rant of a madman, but before stepping in front of the camera, Therrien stopped and delivered another memorable line to McMillan.
"I said to him, watch this," Therrien chuckled.
And when Therrien was finished, he went back to McMillan and said, "How was that?"
He knew McMillan would understand exactly what he was trying to do, which was break the team down so they could start building back up, even if his strategy wasn't clear to everyone at the time.
"I said, Mike, you know what, you did a great job with that rant," McMillan recounted. "He said ahh, no, people are ripping me. I don't think it was good; it didn't play well. I said no, here's why it was good. You were the first person who was appalled at the way we were doing things. He looked at me and says, what's that mean, appalled? I said, you weren't going to take it anymore. He said, you were right. That was his moment of saying I need to change things my way, and it was an important moment for the Penguins. Only a few of us saw it, and it was buried underneath all of that stuff."
That's just one example of how nobody saw the big picture better than McMillan. As someone who covered the Penguins during their tough times in the 80s, and worked for the franchise during their tough times in the '00s, he'd been in enough empty buildings to truly appreciate full ones.
And since McMillan preferred to stay out of the spotlight after transitioning over to the team side, younger generations of Penguins fans may not know him, but they've certainly benefited from all that he's done.
"There are a lot of memories among fans, and they won't have any idea he was behind them," said Mike 'Doc' Emrick, the legendary hockey broadcaster who lunched with McMillan every time he was in town for a national telecast, to learn the news of the day and procure good items he could use that night.
"Special nights on the ice that fans remember to this day, which had to be choreographed by someone and they had to be done with class and taste. If Tom wasn't in charge of all of them, he had input on them."
Prisuta tells a story about the time McMillan - who is famous for bleeding red, white and blue in addition to black and gold, much to the chagrin of his Canadian colleagues - came up with the idea to have a special pregame ceremony to honor the 20th anniversary of Team USA's Miracle on Ice, back when Herb Brooks coached the Penguins.
Despite receiving pushback from Brooks, who, at the time, was in a mindset where he preferred to look forward instead of back, McMillan wouldn't budge. He was adamant that they were going to do the ceremony, since the team was having trouble selling tickets back then.
Despite things getting heated between McMillan and Brooks, it ended up working out for the best.
"That night, I remember looking down at the bench, and Herb took his glasses off and he was wiping his eyes," Prisuta said. "It got bad, but Tom stuck to his guns and said, we're doing this. And it was beautiful. It really was. It was a great night. Herbie appreciated it. When Tom was convinced what the right thing to do was, he was going to do it, and forget the ramifications."
As Bullano Ridgley put it, there are about a million stories like that one during McMillan's tenure with the Penguins. He has played an instrumental role in helping the Penguins become one of the best organizations not just in hockey, but in all of professional sports.
"The things that people enjoy, like season ticket delivery and big screens and things that we've done to engage our fans - he's been a part of all of these conversations," she said. "He has done his part to make the Penguins what they are off the ice."
And even as McMillan advanced through his own career and watched new technologies come into play, he not only managed to keep up with the times, but stay ahead of them. He constantly challenged his staff to come up with new and innovative ways to approach how they did business.
"He's someone that still took the time to learn and to make sure that we were always doing the best of what we could do," Bullano Ridgley said. "I think a lot of the content that we put out, whether it's on social media or PensTV or the website - a lot of these ideas come from Tom. He really has found a way to figure out what Pittsburgh Penguins fans want."
McMillan's progressive and forward-thinking mindset applies to his staff, as well.
In 2008, McMillan promoted Bullano Ridgley - who had started with the team as a graduate intern three years earlier - to Director of Communications, making her the only woman in the league to hold that position.
It was an incredibly significant hire, especially back then, but McMillan wasn't fazed at all by the fact that Bullano Ridgley would be a female working in a male-dominated environment. He believed in her ability, and felt strongly that she deserved a chance.
And not only did he give it to her, but McMillan has since been Bullano Ridgley's biggest advocate as she moved on to become the Penguins' first female senior executive.
"I think the confidence that he instilled in me, and that trust he put in me right from the get go, was probably one of the biggest reasons why I've had success," she said. "When I got into this, I was naive. I just wanted to do this job. I didn't know it mattered if you were male or female. And he made it that it didn't, but he is the person that talks me up more than anyone. He truly is my biggest cheerleader, and I am so grateful for his support and encouragement."
There are so many people who have spent time with the Penguins that are indebted to McMillan for everything he has done to mentor and guide them. Like director of team services Jason Seidling, who worked under McMillan in the communications department for over 10 years before transitioning to the hockey operations side.
"As a young hockey fan growing up in Pittsburgh, I read and listened to Tom every day, hoping to be just like him some day," Seidling said. "I was fortunate to exceed even my wildest dreams, spending over a decade learning the ins and outs of the sports world under the greatest hockey media mind our city has ever had. Outside of my family, nobody has taught me more than Tom, and I'll forever be grateful for that."
But it's not just his employees who have benefited from McMillan's wisdom. McMillan co-founded The Pittsburgh Center for Sports Media and Marketing at his alma mater, Point Park University, in 2011. He has taught at the college alongside Bullano Ridgley, helping students both there and who are interning with the Penguins.
"He always goes out of his way to find out about them and take the time to meet with them," Bullano Ridgley said. "Even though he was getting to the end of his career, he never stopped wanting other people to grow. And I think that's really important with him."
Everyone at the Penguins will certainly miss having McMillan around every day, and not just for advice. Because while his career is legendary, so are his quirks, candor and wit, which has made for many entertaining meals and road trips and stories that aren't quite fit for print.
For example, a restaurant's dinner menu always had to feature his favorite food, salmon - otherwise, the staff would most likely be moving elsewhere. He only drinks Diet Coke and Coors Light (bottle first, then draft, but never a can), loves three-piece suits and his trademmark newsboy cap.
McMillan also has obsessive interests outside of hockey, with his passion for American history - particularly the Civil War and September 11 - famous amongst those who know him. He authored two books on those events during his time with the Penguins, with a third one coming out this month.
"What I will miss the most is walking down the hall, shutting the door, sitting in his office, and talking about something completely unrelated to the Penguins," Morehouse said. "We shared a great interest in history and politics."
But McMillan's colleagues, friends and family are thrilled that he now gets to fully enjoy everything else he loves in life alongside his wife Colleen - like making their annual pilgrimage to Gettysburg to commemorate the battle that took place on July 1, 1863.
That's where McMillan took Lord Stanley's fabled Cup during his day, posing with it next to the burial plot he had purchased there, a picture that perfectly encapsulates who he is - a rare bird.
"Pittsburgh has very few legit hockey lifers, but Tom is. No one has been more dedicated to the cause," said Pittsburgh radio personality Mark Madden. "He's not in the least bit fair-weather. He's a bit like Andy Dufresne: He crawled through 500 yards of excrement and found five Stanley Cups at the other end.
"Tom may know more about hockey than me. Not many do. He definitely knows more about Gettysburg and Flight 93. He's welcome to that, although he has piqued my interest on both subjects. He also knew when to retire: Before Sid did."
McMillan's name is engraved directly above Crosby's on the 2009 Stanley Cup. He's laughed with the Penguins captain before about how people must see his name, and wonder, who the heck is that guy?!
But hopefully, after reading this, Penguins fans realize that McMillan's name belongs there just as much as Crosby's.