The Nurse and Campbell contracts are obvious albatrosses, but I lowkey think that Ken Holland's midrange contracts for league minimum caliber players have been more harmful to the team on a dollar per dollar basis (or at least more harmful than the Nurse contract). Especially considering how frequently and consistently he hands them out. If we had pro caliber GM that cared about player ability instead of player loyalty we'd be able to avoid dumpster fire contracts, many of which turn into cap dumps/dead cap. Zack Kassian, Jesse Puljujarvi, Kailer Yamamoto, Warren Foegele, Kyle Turris, Connor Brown, Duncan Keith, Brett Kulak. Jesus christ.
Ken Holland is by far the worst GM in the NHL.