I actually like Garland more than most, and have no issue with the value in a vacuum, but adding a more expensive contract by trading in a LD for a LW just doesn't make sense according to Boston's roster needs

Boston needs to get cheaper, not more expensive

I wouldn't be happy with this trade (especially as a Bruins fan myself) but I could see this trade being reasonably executed for the Bruins if they are desperate for some forward upgrade due to a sudden loss of forward depth (which may occur with the exits of Bergeron, Krejci, and Bertuzzi all possible). A trade like this may be best rationalized if Boston cannot afford Bertuzzi and acquires a slightly cheaper top nine winger in Garland (for example).

See my reply to CW_73. Not something I believe happens (or should right now) but may be reasonable in more specific, desperate circumstances.

Bold prediction for Dermott and Poolman to return. Very unlikely VAN will re-sign Dermott and Poolman's health is still in question.

Myers' salary includes a 5mil signing bonus which i believe provides little relief in a buyout. According to the buyout calculator, total savings = 666k if VAN were to buyout his final year. Still have a 5.3ml cap hit for nothing. After the bonus is paid, Myers' contract could be an attractive contract (from an ownership perspective) for teams looking to reach the cap floor.

99% chance Poolman doesn't play a game in the NHL again. The Nucks won't resign Dermott, he's a nothing burger.