PROMPT 1:

Being from Boston, I have a long history of choices. I think as a freshly minted 30 year old, it's age appropriate for me to say the Seguin trade to the Stars is the worst trade my team has made. There isn't really anything positive that came from the trade and Seguin has been an all-star in Dallas. I did myself a disservice by looking up his stats in 2018-2019, leading his team, wondering what could have been in Boston.

The runner up is definitely Jumbo Joe to the Sharks. I'm not really sure what that would have looked like for the Bruins in the long run, I would be worried that Joe being there messes up the development of Bergeron and Krejci down the middle. As much as Joe has been an all star in his career and fun to watch, I think this one worked out alright given the cup in 2011.