For the last 15 years, Ken Holland has been regarded as arguably the best general manager in all of sports.
Holland was hired by the Red Wings in 1990 as a professional scout, and after the organization's 1997 Stanley Cup win, Holland was made the general manager.
Since that time, Holland has led Detroit to three more Stanley Cups as well as ten division titles.
Ken Holland has been the mastermind behind numerous free agent signings and trades during his time as the Detroit Red Wings general manager. These deals have kept the Red Wings in contention, and Holland looks to make future deals to keep the Red Wings in contention.
With nearly $6 million in cap space the Red Wings look to be making a deal to improve the team this season, so with that said let's look back at the biggest deadline deals of Ken Holland's career.