I would order it a little differently but I think he hit most of the low spots - Losing Game 7 to Montreal twice in 2004 and 2014 should be there.
The 10 worst Bruins moments of the last 20 years
10. Tim Thomas declines to visit the White House (Jan. 23, 2012)
9. Dave Lewis’ hiring (June 29, 2006)
8. Squandering a 3-0 series lead against Philadelphia (May 14, 2010)
7. Signing Alexei Zhamnov (Aug. 3, 2005)
6. Trading Tyler Seguin (July 4, 2013)
5. Trading Joe Thornton (Nov. 30, 2005)
4. Losing Game 7 to St. Louis (June 12, 2019)
3. Randy Jones cross-checking Bergeron (Oct. 27, 2007)
2. Trading Ray Bourque (March 6, 2000)
1. Matt Cooke knocking out Marc Savard (March 7, 2010)
The 10 worst Bruins moments of the last 20 years
10. Tim Thomas declines to visit the White House (Jan. 23, 2012)
9. Dave Lewis’ hiring (June 29, 2006)
8. Squandering a 3-0 series lead against Philadelphia (May 14, 2010)
7. Signing Alexei Zhamnov (Aug. 3, 2005)
6. Trading Tyler Seguin (July 4, 2013)
5. Trading Joe Thornton (Nov. 30, 2005)
4. Losing Game 7 to St. Louis (June 12, 2019)
3. Randy Jones cross-checking Bergeron (Oct. 27, 2007)
2. Trading Ray Bourque (March 6, 2000)
1. Matt Cooke knocking out Marc Savard (March 7, 2010)