A native of Vernon, BC, Holland helped the Red Wings capture four Stanley Cup championships (1997, 1998, 2002, 2008), the most recent three while serving as general manager.
Over his time as general manager with the Red Wings, Holland guided the team to more combined regular-season and post-season wins (1,044) than any other NHL franchise. The Red Wings reached the playoffs for his first 19 seasons as general manager, giving the organization 25 consecutive seasons in the NHL post-season (1990-2016).
Prior to taking over as general manager of the Red Wings in 1997, Holland served in a number of different roles within the organization, including as assistant general manager (1994-97), general manager of the Red Wings' American Hockey League affiliate (1994-97), amateur scouting director (1987-94) and western scout (1985-87).
Internationally, Holland has served on several management staffs for Hockey Canada, winning gold medals at the 2010 and 2014 Olympic Winter Games and at the 2016 World Cup of Hockey.
As a goaltender, he was drafted by Toronto in the 12th round, 188th overall, in the 1975 NHL Entry Draft, reaching the NHL for four games with Hartford and Detroit. Holland retired as a player after the 1984-85 season, transitioning soon afterwards into scouting.
Holland played two seasons of junior hockey with the Medicine Hat Tigers from 1973-75 and later resided in the city from 1985-1994 working as a Western Canadian scout for the Red Wings.
Holland and his wife Cindy have four children: Brad, Julie, Rachel and Greg.