What happened: Montreal acquired Anderson in October 2020 before signing him to a seven-year, $38.5 million contract. He has remained with the Canadiens through uneven offensive stretches and several playoff runs.
Why it matters: Anderson scored an overtime winner in Game 4 of the 2021 Stanley Cup Final, extending Montreal's season. The deal delivered a long-term power forward without sacrificing a lasting cornerstone.
By the numbers: Anderson scored 27 goals in 2018-19 before injuries limited him to four points in 26 games the next season. The forward sent away by Montreal recorded 56 points in 107 games following the trade.
What to watch: Anderson's role in the upcoming 2026-27 season will shape the deal's longer-term assessment.