He reached 914 wins, passing Jack Adams for the most by a general manager in the Red Wings' 92-season history, when they defeated the Ottawa Senators 2-0 at Canadian Tire Centre on Saturday.
What happens in the offseason remains to be seen. The Red Wings (21-25-7) are 27th in the NHL standings and likely will miss the Stanley Cup Playoffs for the third straight season.
Whatever happens, though, Holland wants to have set the foundation for their next run.
"I've got a year to go on my contract," Holland said Tuesday. "Obviously there's lots of rumors, and there's things swirling out there. We'll see what the summer brings.
"I love the job. I still believe I've got lots of energy. And I guess I would say to you, as I go forward, you never want to stay …"
He didn't finish the sentence.
Later, he said: "I've got to make sure that I do what's right. I don't know what the future's going to bring. I don't want to overstay. You never want to overstay.
"I used to crack jokes that when [defenseman Nicklas] Lidstrom was gone, I was going out the door with Lidstrom. It was a little bit tongue-in-cheek, but it was also about how important Lidstrom was to the team. He left in 2012. It's 2019 here, and I'm still here. I've overseen a rebuild."
To put those comments in context, Holland has had a dream job with the Red Wings. He has spent most of his adult life working for them, has enjoyed incredible success with them and is loyal to them because of it.
Holland was born in 1955. He grew up a goalie and a fan of the Toronto Maple Leafs, who won the Stanley Cup four times in his formative years. After Maple Leafs games, he'd play road hockey in the dark, pretending to be Johnny Bower and Terry Sawchuk.
Though the Maple Leafs selected him in the 12th round (No. 188) in the 1975 NHL Draft, he never got to play for them. He played four NHL games amid a nine-year professional career: one for the Hartford Whalers in 1980-81, three for the Red Wings in 1983-84.
His true ticket to the NHL came when the Red Wings hired him as western Canada scout in 1985. He has been with them ever since, even though he has had multiple opportunities to leave, rising through the ranks and moving to the Detroit area in 1994. Only senior vice president Jimmy Devellano, hired as GM in 1982, has spent more time in their front office.
"You go from pretending to be those guys to being in the NHL and eventually working my way to being a general manager of [Steve] Yzerman and a general manager of Lidstrom and a general manager of [Dominik] Hasek and [Chris] Osgood and [Mike] Vernon and the Russian Five," Holland said. "It was magical. It was surreal."
Holland appreciates his good fortune. He compared working with Devellano and coach Scotty Bowman to going to Harvard. When he was promoted to GM in 1997, the Red Wings were the Stanley Cup champions. Few GMs take over teams at the top.
But under Holland, the Red Wings stayed there for a long, long time. They won the Cup again in 1998, 2002 and 2008, and nearly again in 2009, losing to the Pittsburgh Penguins in Game 7 of the Final. They made the Stanley Cup Playoffs each season through 2015-16, stretching their playoff streak to a quarter century.
They did it while changing coaches, going from Bowman to Dave Lewis in 2002, Lewis to Mike Babcock in 2005 and Babcock to Jeff Blashill in 2015. They did it while turning over most of the roster. Only five players were part of the last four championships: Lidstrom, Kris Draper, Tomas Holmstrom, Darren McCarty and Kirk Maltby.
They won with a huge payroll. Then, after the NHL instituted the salary cap in 2005, they cut their payroll from $80 million to $39 million and kept winning. When they finally missed the playoffs in 2017, they were the last team to do so under the cap.
Despite their recent struggles, they still have the most wins (914) and points (2,065) in the NHL since Holland became their GM.
Holland credits everyone from the owners to the executives to the scouts to the coaches to the players. The list is too long to include here.
"Certainly I'm proud of the record," Holland said. "My name is there. But it's a whole bunch of people on the ice and off the ice, talented people, that really have made these 914 wins happen."
Holland is well aware of the criticism of him.
"Some people think you've overstayed when you miss the playoffs," he said.
But every team goes through cycles, especially under the cap.
The Chicago Blackhawks won the Cup in 2010, 2013 and 2015; they have 51 points this season, two more than the Red Wings. The Los Angeles Kings won the Cup in 2012 and 2014; they are 29th in the NHL standings with 48 points.
"I understand that you get a period of time when you're going to be good, and then you've got a period of time when you've got to rebuild," Holland said. "That's just going to be the reality of the National Hockey League. I look at the teams that are rebuilding or at the bottom of the standings. Some of them have been some of the great teams in the League."
The Red Wings were long overdue.
"Possibly a rebuild should have started to happen in 2005 and 2006 when [Sergei] Fedorov was gone, when Yzerman was gone, when [Brendan] Shanahan left, when the Russian Five were gone," Holland said.
The Red Wings kept their window open as long as they did largely because they had Lidstrom, one of the best defensemen in NHL history, and found centers Pavel Datsyuk (No. 171 in 1998) and Henrik Zetterberg (No. 210 in 1999) late in the NHL Draft.
Those players are gone, and the Red Wings don't have the difference-makers they once did. During their playoff streak, because they were winning and trading picks, their average first pick was No. 38.
Once it was clear their streak was about to end, they started accumulating picks. They selected 21 players over the past two drafts, including forwards Michael Rasmussen (No. 9 in 2017) and Filip Zadina (No. 6 in 2018), their first top-10 picks since 1991. They feel they have several promising prospects as a result.
They have 11 picks in this year's draft and will have cap space this offseason too.
"I'm really happy with the job that our people have done in the trenches in amateur scouting, in pro scouting, at the coaching level, our players," Holland said. "I really believe that we're headed in the right direction and that we've got young players coming through the system that are eventually going to get this team back to being more relevant, more competitive, a playoff team.
"And we've got the greatest fans in the world. I reflect back on those Stanley Cup parades where there's a million people out there … and what this team means to this city and to this state to Red Wing fans worldwide, but at the same time what those same people mean to our franchise.
"So I've got to make sure that I make decisions going forward that are what's right for this franchise."
Holland is 63.
Nashville Predators GM David Poile turns 69 on Feb. 14. Pittsburgh Penguins GM Jim Rutherford turns 70 on Feb. 17. New York Islanders GM Lou Lamoriello is 76.
Poile has been in one place since 1997, like Holland, and is still contending for the Cup, although he has never won it. Rutherford and Lamoriello each was synonymous with a Cup-winning franchise like Holland is -- Rutherford with the Whalers/Carolina Hurricanes, Lamoriello with the New Jersey Devils -- then reinvented himself elsewhere.
"I've got a ton of energy," Holland said. "I've got a plan. I've got a vision. The vision is to get this team back to being more competitive, back in the playoffs, so our fans can come down to Little Caesars Arena in April and root their team on.
"There's other general managers in the League ... older than I am, and they're having a ton of success. Certainly I look at that. But I've also been around long enough that I've seen people come and go, and they're gone before they hit anywhere near my age. I certainly reflect on all that at times.
"I'm not really giving you an answer on my career as to when it's time to leave. But I guess what I am saying is, I'm going to make the decisions that I think are in the best interests of the Detroit Red Wings, because it's been a magical, magical run."