Inside the Penguins’ quiet, persistent pursuit of Kyle Dubas

Four miles, the majority of them along U.S. Highway 19, separate the Penguins’ practice facility and Il Pizzaiolo, a go-to Italian restaurant for team employees in Warrendale, Pa. The eatery is about a 10-minute drive from where Kyle Dubas spent a good bit of his time over the final days of May. Its storefront indistinguishable from about a dozen suburban strip malls in the area, the restaurant, a favorite for locals because of its meatballs, custom wines and imported-from-Italy toppings for fried pizzas, now occupies a small slice of Penguins history.

Advertisement

The day Dubas toured Pittsburgh with his family, as the Penguins continued their offensive to hire the newly available, in-demand executive, he ate takeout from Il Pizzaiolo for lunch and dinner. Four days later, he was officially announced as the Penguins’ president of hockey operations, beginning a new — and urgent — era for the franchise.

Six weeks earlier, Penguins alternate governor Dave Beeston had publicly pledged a thorough process to find new hockey leadership. The process was far from that simple.

The Penguins pursued Dubas as though he was still a wunderkind, even though his tenure as general manager in Toronto had produced only one series win in five postseasons. Dubas had given reason for the Maple Leafs’ tens of millions of fans to believe they could host a Stanley Cup celebration for the first time since 1967, but his run ended suddenly amid speculation of a power struggle with his boss in Toronto. His very commitment to a job unfinished was questioned by Maple Leafs president Brendan Shanahan, and Dubas was dismissed within a week of reportedly being offered a new contract and merely days after telling the media his future was “either Toronto or nowhere.”

The Maple Leafs had not won a playoff series since 2004 before Dubas’ latest and last roster reached the second round of the 2023 postseason. Perceived as a multifaceted manager who blended scouting, analytics, outside-the-box thinking and mastery of the salary cap, Dubas had delivered perennial top-tier results in the regular season. His teams had star power, depth and scoring, but never quite enough to put together a lengthy postseason.

Still, at only 37 years old, Dubas was generally seen within the tight hockey community as having his best days as a hockey decision-maker ahead of him. Only two management openings existed at the time of his firing by the Maple Leafs, and one of those was an opportunity with the flagship franchise of the league’s cap era: the Penguins, whose new-ish ownership group had privately pined over him for all the obvious reasons. He was inquisitive, detailed, driven, communicative and experienced — seemingly a perfect fit in Pittsburgh, where the brand was stars and skill as much as on-ice success.

Advertisement

Three of the previous four GMs in Pittsburgh had combined for the Penguins’ five Cup wins and 27 postseason appearances since 1991. Craig Patrick, Ray Shero and Jim Rutherford had become mainstream managerial stars for their work.

Fenway Sports Group, which purchased the Penguins midway through the 2021-22 season, had its first opportunity to make a hockey hire. The front-office equivalent of Sidney Crosby was not a prerequisite, but it would be on-brand for the Penguins. And Dubas could represent what Crosby had almost two decades prior: hope and glamour.

The Penguins’ interest in Dubas had been one of the NHL’s open secrets since before FSG fired GM Ron Hextall, president of hockey operations Brian Burke and assistant GM Chris Pryor on April 14. Over parts of three seasons, including a chaotic final year, the Penguins had gone from a division winner to missing the playoffs under Hextall and Burke — and behind-the-scenes drama made their decline all the more embarrassing.

Dubas had a job at the time, and nobody with FSG figured he would be available after the Maple Leafs won their first Stanley Cup playoff series in two decades, so the Penguins set forth on one of the most important ventures in franchise history — finding the hockey boss for the rest of Crosby’s career. A year after Crosby successfully helped keep longtime teammates Evgeni Malkin and Kris Letang in Pittsburgh, the Penguins were the NHL’s oldest team, a franchise with only one series victory in five years, and a championship window that was closing.

Neither FSG nor Crosby, an all-time great still performing at a very high level, were keen to see that window close.

Between his parting with the Maple Leafs (May 19) and his hiring in Pittsburgh (June 1), Dubas visited Western Pennsylvania three times. Traveling the first time in his own car and the final time on FSG’s private jet, Dubas — along with his wife and two children — were wooed practically every way possible, starting with a phone call to Dubas from FSG chairman Tom Werner the morning after he parted ways with the Maple Leafs.

Advertisement

A few hours after that call on May 20, Dubas was on a flight to Boston, FSG’s home base, for face-to-face meetings with Werner, Beeston and Sam Kennedy, and FSG owner John Henry at Henry’s house. And with that meeting, a search led by Beeston for new hockey leadership in Pittsburgh took a hard left turn.

FSG wanted to conduct the search as quietly as possible, and Beeston was mostly successful in keeping a tight lid on whom he did and didn’t interview. Beginning the week of May 15, candidates who made it past the first round were welcomed to Boston by the same FSG group that Dubas would meet that weekend. Those candidates included current assistant GMs Dan MacKinnon (Devils), Eric Tulsky (Hurricanes) and Mathieu Darche (Lightning), along with Steve Greeley, a director of hockey strategy (Stars). By May 18, Darche and Greeley emerged as FSG’s preferred candidates, and negotiations were to begin over the new few days.

As FSG was inching toward its future, drama began playing out in real-time for Maple Leafs Sports & Entertainment, the ownership group in Toronto.

Far from a Friday news dump, this development shifted the earth beneath two of the NHL’s most prominent franchises. Sensing an opportunity to finally engage with Dubas, the Penguins sought permission to speak with him from the Maple Leafs, and Werner called Dubas to invite him to Boston.

Dubas met with FSG personnel on May 21 in Boston before returning to his Toronto home. Two days later, Dubas drove to Pittsburgh to tour the Penguins’ facilities, meet with coach Mike Sullivan, take in some scouting meetings at the practice facility and — in an unexpected nightcap — watch Game 3 of the Western Conference final with Crosby, who happened to be in Pittsburgh for a short stop between vacation trips. Dubas was excited to meet Crosby, but nobody with the Penguins — at least among the handful of employees who knew Dubas was in Pittsburgh — could guarantee the logistics would work out. The former prodigies did what hockey people do, if possible, when they’re trying to break the ice: swap stories while watching a hockey game.

Dubas drove back to Toronto the next day. At that point, he was already thinking about a proposed return to Pittsburgh with his family. The Dubases flew to Pittsburgh on May 27 and toured the city — mostly the northern suburb where the Penguins practice — the next day. By then, the close circle of people aware of Dubas’ dealing with the Penguins expanded from FSG’s top brass, Penguins president of business operations Kevin Acklin, and Sullivan, to also include only a few select employees, including senior vice president of communications Jennifer Bullano Ridgley and director of team operations Jason Seidling.

By the time Dubas ate Il Pizzaiolo and toured the area with his family, FSG had done everything it could in its mad-dash pursuit to sell Dubas on running the show in Pittsburgh.

Advertisement

Despite the red carpet treatment he received, Dubas tried to pay for the lunch-time takeout order but was told the meals for him and his family were taken care of by the club. Sensing his kids might want to eat something else, Dubas drove to a nearby McDonald’s. When he returned for more meetings, Dubas brought McDonald’s for the few Penguins employees who hadn’t yet eaten and knew a tightly-guarded secret: Dubas and the Penguins were close to doing business.

Beeston joked that he would name Dubas emperor of hockey if it closed the deal. But he didn’t need to.

On May 29, Dubas boarded a private jet to Boston. There, he again met with FSG’s Henry and Werner, and Dubas and Beeston also worked out the finer points of his contract. He had sought, and received, full autonomy in hockey decisions, but figuring out a title was still tricky. Upon buying the Penguins, Beeston had presumed Burke controlled hockey operations because of his title. To his surprise, Beeston discovered that Burke was no more than a figurehead and had very little power, which instead belonged to Hextall.

Dubas was not coming to Pittsburgh as a GM, as he had been with the Maple Leafs. He wanted the final say on all hockey decisions, and FSG was in agreement. But what to call him?

Dubas and Beeston decided on president of hockey operations — and neither cared if there might be some confusion given Burke’s previous role.

After two days in Boston, Dubas and FSG officers boarded the private jet for an evening flight to Pittsburgh on May 30. The Penguins had their man, and Dubas had a seven-year contract with a $5 million annual salary and use of FSG’s private jet for family travel. The announcement was made at 10:30 a.m. the next day, after Beeston informed Darche and Greeley they were no longer candidates.

In all, the process to determine and appoint a new hockey boss in Pittsburgh took 42 days, several clandestine meetings, multiple trips between Toronto and two American cities, and at least two takeout orders of meatballs.

(Top photo courtesy of the Pittsburgh Penguins)