I haven't watched the video yet but title seems pretty alarmist.
it's not like Dame asked out from a team that did everything they could and didn't miss any opportunities.
* Portland drafted Meyers Leonard when Draymond Green and Khris Middleton were available
* they drafted CJ when Giannis was available
* they made max offers to Roy Hibbert, Enes Kanter, Greg Monroe and Chandler Parsons
* they traded for Afflalo using a 19th pick in a draft when at 19, Siakam, Dejounte Murray, and Malcolm Brogdon was available
* they refused to include CJ in trade talks for Paul George and Jimmy Butler
* The used a 15 + 20 pick for Zach Collins when they could have had a combo of Adebayo, Donovan Mitchell, John Collins, Jarret Allen, and OG
* they traded cap-space for Anderson Varejao to secure a 1st round pick, spent millions of dollars on the pick, then used it for Swanigan
* They traded Gary Trent for a 6'3 guard who plays bad defense than tried to run a starting unit of 6'2, 6'3, 6'3, and 6'7
* They traded two 1st round picks for Covington, then dumped him to get under the tax
* then they traded a 1st round pick for Nance and locked up all of Portland's 1st's for 7 years
* they have a penny-pinching ownership group that seems to care more about money than fielding a competitive team
so I'd wonder, would Dame have asked out if the Blazers had not made all of those terrible moves or missed all of those great opportunities. Is this situation because Portland is a small market or because Portland had a decade of GM malpractice?