During the 2024 playoffs, the Edmonton Oilers went on quite the run. After going through three rounds, they made the Stanley Cup Final where they fell 3-0 in the first three games and rallied back to force a game seven but unfortunately lost to Florida.
Holland's tenure in Edmonton was a mixed bag. He was able to build a team that made the Stanley Cup Final but also made many questionable moves. Among the questionable moves, the Milan Lucic contract, the Darnell Nurse contract, and the Jack Campbell contract stand out.
However, he did make some great moves as well like signing Zach Hyman to a contract that only sees him make $5 million a year. This may go down as the best move of the decade given how productive Hyman has been.