What happened: The Ottawa Senators sent Alexei Yashin to the New York Islanders in 2001 for Zdeno Chara, Bill Muckalt and the No. 2 pick used on Jason Spezza. Subsequent deals involving Spezza and Nick Paul ultimately yielded the 2024 fourth-round pick used on Montgomery.
Why it matters: Chara and Spezza became franchise cornerstones, giving the original deal lasting significance beyond its remaining asset. Montgomery, 21, now carries the final branch into the 2026-27 season on a three-year entry-level contract.
By the numbers: Spezza recorded 251 goals and 687 points in 686 regular-season games for Ottawa. Montgomery produced nine goals and 17 points in 38 NCAA games before scoring one goal in three games with Belleville.
What to watch: Montgomery's progress in the professional ranks will determine how long the chain remains active. His entry-level contract begins in 2026-27.