John LeClair: Five years, $45 million, signed in 2001.
A onetime superstar, LeClair saw his production dip dramatically after he signed, and he was bought out before the deal expired, helping the Flyers meet the new salary-cap requirements.
Danny Briere: Eight years, $52 million, signed in 2007.
Briere, one of the classiest players in franchise history, spent six seasons in Philadelphia after signing. He scored 31 goals in his first season with the Flyers, helping them reach the conference finals after having the league's worst record the previous season. Briere was brilliant in the playoffs, especially in 2010, when he scored 30 points and led an improbable charge to the Stanley Cup Finals.
Hindered by injuries, Briere was ineffective the last two seasons and the Flyers are buying out the last two years of his deal, wiping out an annual $6.5 million cap hit.
Mike Richards: 12-year extension, $69 million, signed in 2007.
The gritty Richards had several highly productive seasons with the Flyers before they traded him to Los Angeles in 2011. They have maintained they dealt their captain simply because of the return (Wayne Simmonds, Brayden Schenn) they received. It's also possible the trade was made because the Flyers did not like Richards' off-ice lifestyle.
Richards was traded nine years before his contract with the Flyers would have expired after the 2019-20 season.
Jeff Carter: 11-year extension, $58 million, signed in 2010.
A stunned Carter was traded seven months after signing his big-bucks contract. He averaged 38 goals per season in his last three years with the Flyers.
As with Richards, the Flyers' party line for dealing Carter was this: It was all about the return - Jake Voracek and draft picks that turned into Sean Coutuier and Nick Cousins. You can believe that, or you can refer to the Richards theory.
Carter and Richards, of course, both won Stanley Cup rings with the Jonathan Quick-led Kings in 2012.
Chris Pronger: Seven-year extension, $34.9 million, signed in 2009.
With the snarling, crease-clearing Pronger in the lineup, the Flyers had an identity - and they went to the Stanley Cup Finals in his first season with the club. But the team seemed to lose its edge after Pronger went down with a career-ending concussion in 2011.
Because of the injury, Pronger was able to play only two-plus seasons with the Flyers, who acquired him from Anaheim for a pair of No. 1 picks, Joffrey Lupul, and Luca Sbisa at the 2009 draft.
Ilya Bryzgalov: Nine years, $51 million, signed in 2011.
Financially, the signing was a Bryzaster. Bryzgalov was paid like a star, but his mediocre play (2.61 goals-against average, .905 save percentage) caused the Flyers to cut ties two years into the deal. The Flyers announced Tuesday that they were buying out the remaining seven years of his contract.
When the checks stop coming, Bryzgalov will have been paid a little more than $39 million for his two years in Philadelphia.
Giroux's agent is talking with general manager Paul Holmgren about a long-term deal. The new collective bargaining agreement limits the length of contracts to a maximum of eight years (seven if it's a player who is new to the team).
The Flyers hope Giroux will fall into the same category as Kimmo Timonen, a player who signed a long-term deal (six years, $37.8 million, signed in 2007) and was actually productive.
Contact Sam Carchidi @phillynews.com. Follow on Twitter @BroadStBull.