Simple answer: There is a MASSIVE gap between the talent of Winslow and the scrub we selected #16. Danny knew this. Riley knew this. Boston tried to give up 6 draft picks to Charlotte with hopes that they didn't know this... but it didn't work out.
Funny thing is, with 11 games left in the season, we were actually basically tied with Charlotte. Al Jefferson and MKG both get hurt, Charlotte loses 9 of the last 12 games... Boston wins 9 of their last 11... and the entire future of this team is impacted as a result. Whether it was for better or for worse, we will not know until the end of free agency.
Don't know why the better or for worse needs to be debated. I wanted to make the playoffs, do not regret it, but the best course of action (rebuild wise) is quite clear that higher draft pick is always to the benefit.
That said, that doesn't mean that making the playoffs is without value, but it's not as tangible either.
So all the tankers doing the chest pumps I don't know what they're going on about honestly. It's not like wanting to make the playoffs, and the cost of it, was unknown. And if one wanted to make the playoffs, and wasn't aware of the potential costs/risk, then lesson learned for you (not you you, the general you).