This isn't new for Portland. Back in 2020, the Blazers were down to around the #5 spot in the Lottery before for going on a bit of a run to finish 35-39. That year, the Lottery wasn't great (did we even have a pick?), but we would have finished around where we are now but instead of tanking, they beat some of the other tanking teams to squeeze into the Playoffs and get trounced.
The whole philosophy of smaller, offensive minded with little defensive impact players has not boded well. Even if it has taken them to scraping into or higher ranked Playoff spots, the result has most often been a quick dismissal. The year they beat the dysfunctional Thunder and then the baby Nugz, is the exception that almost proves the rule. This team needs a complete retooling, length, defensive chops, and some 'dog' to them. And it is tough to see where Billups would be the guy that would get the most out of that group even though it seems like that might be his basketball lineage.