The reported 14-year, $100 million-plus deal, announced by the Flyers on Thursday, is just the latest in a litany of aggressive moves that have marked Holmgren's tenure in Philadelphia.
Holmgren's fearlessness can be traced to his first day on the job, Oct. 22, 2006, when he fired Stanley Cup-champion coach Ken Hitchcock and replaced him with first-year NHL assistant John Stevens.
By making a massive offer sheet to All-Star defenseman Shea Weber, Flyers' GM Paul Holmgren proves again he is ready to make unexpected moves. (Photo: Getty Images)
In nearly six years on the job, Holmgren has changed coaches twice, he's traded his team's captain twice, he's never hesitated to go after the biggest catch in the free-agent market, and he's been aggressive in pursuing trades.
Holmgren's Stanley Cup trophy case might be empty, but no general manager since 2006 has been as aggressive in his pursuit of one.
The team Holmgren inherited when he replaced Bob Clarke was headed for the worst finish in club history and last place in the NHL standings. However, he started to dig out from that hole at the 2007 trade deadline. He sent Peter Forsberg to the Nashville Predators for forward Scottie Upshall, defenseman Ryan Parent and a 2007 first-round draft pick.
After the Predators lost in the first round of the Stanley Cup Playoffs, Holmgren worked another deal with Nashville, acquiring the negotiating rights to impending free agents defenseman Kimmo Timonen and forward Scott Hartnell.
"We agreed to a timeframe where I could talk to the players themselves, and if we came to an agreement with those players, there would be a return for Nashville," Holmgren has said. "If we could only sign Timonen it was a certain price, if we could only sign Hartnell it was a certain price, and if we could sign both it was the first-round pick."
The Flyers signed both and in return sent the first-round pick they had acquired from Nashville in the Forsberg trade back to the Predators. It was the first time in the post-lockout era that a team had acquired the rights to impending free agents.
All the new faces got the Flyers to the 2008 Eastern Conference Finals, proving Holmgren had the blueprint to build a winning team.
That offseason he allowed Smith to leave as a free agent and appointed 23-year-old Mike Richards team captain. Three months later, Holmgren signed him to a 12-year, $69 million contract.
In the summer of 2009, Holmgren again showed his willingness to gamble, trading Lupul, 2008 first-round pick Luca Sbisa and a 2009 first-round pick to the Anaheim Ducks for outspoken defenseman Chris Pronger.
Pronger added a combustible element to the locker room, and the result was a slow start to the 2009-10 season. Holmgren reacted by firing Stevens and bringing in Peter Laviolette. The players who were closest to Stevens chafed under the demanding Laviolette, but the team improved, earned a playoff spot in a dramatic last-day shootout win against the New York Rangers and made a historic run to the 2010 Stanley Cup Final, losing to the Chicago Blackhawks in six games.
After watching the poor performance of his goaltenders in the 2011 Stanley Cup Playoffs, Holmgren again acted swiftly, acquiring the negotiating rights to goalie Ilya Bryzgalov and signing him to a nine-year, $51 million contract before he could reach free agency.
With Pronger's return to health doubtful after suffering a serious concussion last season and the free-agent departure of Matt Carle, Holmgren has been active this summer in rebuilding his blue line. He traded young forward James van Riemsdyk -- months after signing him to six-year contract extension -- to the Toronto Maple Leafs for Luke Schenn, then lured Weber, an elite player who was runner-up for this year's Norris Trophy.
While the Flyers remain in search of that elusive third Stanley Cup in team history, Holmgren has proven he won't rest until he wins one.
Contact Adam Kimelman at firstname.lastname@example.org. Follow him on Twitter: @NHLAdamK