2016 and beyond:
The Blackhawks just do not like second-round picks. They gave up a 2018 second-round pick and Phillip Danault in a trade with the Montreal Canadians. The second-round pick turned into defenseman Alexander Romanov who recently played his first NHL season and is still going with the team in the postseason.
Honestly, this one season buying in at the deadline killed the team in itself. Chicago also sent a first-round pick and Marko Dano to Winnipeg for Andrew Ladd. The first-round pick turned into German Rubtsov who played in four games with the Flyers during the 2019-20 season.
In 2017 the team gave up a 2018 fourth-round pick and Mark McNeill for Johnny Oduya then on the Dallas Stars. They also brought in Tomas Jurco from Detroit for a 2018 third-round pick who turned into Keith Petruzzelli.
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With 2017 over that would be the end of the team buying at the deadline and giving up assets. While they did do their best to bring in some talent and depth during the summers when they had to trade away players like Brandon Saad or Andrew Shaw, eventually the price of giving up first-round picks and second-round picks was just too high a cost.