The last transaction between the Habs and Hawks also involved Alex Romanov

First, he traded defenseman Alexander Romanov with the 98th pick of the draft to the New York Islanders for the 13th overall pick at the time, before trading him to the Chicago Blackhawks with the 66th pick of the draft for center Kirby Dach.

Ironically, the last trade between the two teams, between Montreal and Chicago in February 2016, was similar to say the least and turned out pretty well for the CH. That trade also involved Alexander Romanov, in a way, as the 2nd round pick acquired was used to draft him with the 38th pick of the 2018 draft.

Dach, 21, was drafted third overall in 2019 by the Chicago Blackhawks and has 59 points (19 goals) in 152 career NHL games. Many around the league believe he is unable to score, especially with the wrist injury he suffered while playing for Canada at the 2021 World Junior Championship. The solution with the CH is quite simple if you believe Nicolas Cloutier of TVA Sports:

Romanov has 4 goals and 15 assists in 133 NHL games, all with the CH. He also added a goal in 4 playoff games with the club.

The decision to trade the Russian defenseman must have been a tough one when you consider what happened the last time the CH made this kind of deal with Sergachev, but it was inevitable. With the number of young left-handed defensemen knocking on the door, most notably Kaiden Guhle, the space was starting to run out. More changes to the defense, especially regarding Jeff Petry, are certainly coming...