The Philadelphia Flyers handed out some regrettable contracts during the latter years of Paul Holmgren's run as general manager, especially when it came to their defense.
The most regrettable of the bunch has to be the six-year, $30 million extension they gave to Andrew MacDonald back in 2014.
How bad of an investment did it turn out to be?
Well, consider this: The Flyers announced Monday, one year into the contract, they are placing MacDonald on waivers. He still has five years and $25 million remaining on the deal, and it is almost certain that he will go through waivers unclaimed.
It is expected that MacDonald will play in the American Hockey League, if he clears waivers. He would still count $4.05 million against the Flyers' salary cap at that point.
MacDonald was acquired by the Flyers from the New York Islanders late in the 2013-14 season. After appearing in a handful of games, was given his massive contract extension.
What makes it especially damaging for the Flyers, aside from the size of the contract, is that the team has had its share of salary cap problems (due in large part to contracts like this) in recent years. It also cost them two draft picks -- a third-round pick in 2015 and a second-round pick in 2014 -- and a prospect to acquire him.
The Islanders used the second-round pick in 2015 they acquired from the Flyers as part of their package to trade for a significantly better defenseman -- Johnny Boychuk -- from the Boston Bruins prior to the 2014-15 season.
You can't blame MacDonald for this situation because he is what he is: A defensive-defenseman that doesn't provide any offense or much of a puck-moving presence on the blue line. He simply did what any other person would do in the same situation and took the huge payday that was offered to him. The blame lies entirely on Flyers management for simply making a bad decision and a bad investment.
Even as NHL teams transition to more mobile, puck-moving defensemen, there can still be a place for players like MacDonald on a roster. However, you can't pay them $5 million a year over six years and expect them to be top-pairing guys.
The Flyers' defense is easily the weak link of the roster heading into the season. With MacDonald on waivers, his future with the team is obviously uncertain. The Flyers are prepared to open the season with a 37-year-old Mark Streit leading the unit, while Luke Schenn, Michael Del Zotto, Nick Schultz, Radko Gudas and free agent Evgeny Medvedev (signed out of the KHL) round out the group.
They're going to need another great season from goalie Steve Mason to stay competitive in a tough Metropolitan Division.
Earlier this summer, the Flyers sent two more of their problem contracts on defense -- the ones belonging to Chris Pronger, who will never play another NHL game, and Nicklas Grossmann -- to the Arizona Coyotes for Sam Gagner and a conditional draft pick.
All of these deals -- Pronger, Grossmann, MacDonald -- were signed when Holmgren was still general manager.