The Contract: 8 years - $6.875M AAV ( 2015)
Brent Seabrook is a Blackhawks legend, playing a total of 1114 games with the franchise, while adding 103 goals, 361 assists and 464 points. Seabrook was a really solid player, and will likely go down as one of the best Hawks defensemen in franchise history. He was apart of the teams Stanley Cup runs, and is a three time champion, winning all three with the Hawks.
Unfortunately, near the end of his career that was stopped early due to injury, Seabrook wasn't playing all that great. In the 2017-18 season, he played 81 games, had 7 goals and 19 assists for 26 points, which isn't terrible, but his play was very clearly declining. The 2018-19 season was more of the same. In 78 games played, Seabrook had 5 goals and 23 assists for 28 points, but his plus minus fell to a -6. The 2019-20 season was a huge decline, as he only appeared in 32 games, with a 4 point performance to show for it.
Injuries ended Seabrook's career early, and if he had stayed fully healthy I don't think this contract would've looked as bad as it did. But, during the 2020-21 season, the Hawks took on the full $6.875M cap hit and he didn't appear in a single game. The Hawks eventually traded Seabrook's rights to the Lightning for Tyler Johnson, who has battled injuries for a while, but will likely be a huge member of the top 6 forward core for this upcoming season.