Sometimes, severing old ties and connections is difficult.

Kyle Dubas has been running the Pittsburgh Penguins since June 1, 2023, but will soon be featured in a book by Craig Custance documenting his days with the Toronto Maple Leafs.

Considering that Dubas was the Maple Leafs’ GM for five seasons, there’s no denying that running an Original Six franchise in arguably Canada’s top hockey market is challenging, and there are plenty of stories to tell.

In Custance’s book, “The Franchise: The Business Of Building Winning Teams,” which is expected to be released on Oct. 17, 2024, the author goes behind the scenes with Dubas to discuss this tenure with the Maple Leafs.

The Penguins GM still has no problem with his pursuit of John Tavares. He inked the former New York Islanders captain to a seven-year contract valued at $77 million that expires next summer.

However, if Dubas could go back in time, he would like a do-over regarding how he handled the Auston Matthews, William Nylander, and Mitch Marner contract extensions in 2018 and 2019.

Now, if this all seems too familiar and fresh in people’s minds, it’s because Dubas has yet to sign Penguins captain Sidney Crosby to an extension, even though he’s been eligible since July 1.

Realistically, most of the hockey community outside of Pittsburgh wants to see Crosby skate a Stanley Cup-contending team and retire a champion.

Yet, the Penguins fanbase still believes they are contenders and don’t want to see their beloved captain wear any other colors.

So Dubas is back to a career crossroads moment he was just in about five years ago.

As the face of the franchise winds down his Hall of Fame career, does the GM pivot the franchise’s direction to think past the next three seasons, or does he go in and hope the boys currently in the room have one more run in them?

When Matthews, Marner, and Nylander needed new deals, each skater was in their early 20s with endless opportunities ahead of them. Those contracts aimed to keep the band together for as long as possible.

Dubas doesn’t have those same luxuries today, especially after acquiring Erik Karlsson, who eats a significant portion of the Penguins’ salary cap.

Like the Tavares deal, a decade from now, Dubas may say bringing in Karlsson was a great move and that he wouldn’t change his decision to pursue the former Norris Trophy winner.

But on the flip side, the longer the Crosby extension story plays out, the more it becomes a distraction, with every social media post scrutinized, especially if the whole thing drags on as the young guns in Toronto did.

Either way, reading about Dubas’ actions in trying to build a winner in the most demanding professional hockey market on the planet should make for a good read when Custance’s book comes out in the fall.

A new chapter might or might not need to be added after the Crosby extension is announced because his handling of the situation appears to be following a pattern he was in not that long ago.