Please forgive the somewhat free form nature of this post. I started writing it to help me figure out my own feelings about the trade, because I had a very negative reaction to it when the news broke. I had really hoped that the team and Crawford could work something out, but through the process of writing down my thoughts I came to the conclusion that it probably couldn't have gone too much different.
Not every player is going to be able to develop the way you want them to. Because so much of that is a personality thing. And I'm not putting it all on Jordan Crawford like saying he's a bad guy or he can't develop in other ways, but just that as far as the character that the team wanted and the approach to the game that Crawford has aren't a good match. Maybe it could have changed, maybe it couldn't have. Personalities clash, and Crawford may not have wanted to change his game to what the Wizards wanted it to be. Doesn't seem like his personality, in his quotes he's always sort of a fun, easy-going "this is who I am and it's gonna do what it's gonna do" kind of guy. But about 90% of this goes on at practice, off the court, etc. so it is just speculation based on reading the quotes from all the people involved.
I'd say you could look at it as a scouting issue but it's not like the Wizards drafted Crawford, he was sort of a throw in on the Hinrich trade. The way I see it Wiz took a shot on him, there was some mutual benefit for both sides but ultimately it had probably run it's course. It's a shame that we didn't get more for him but I do think from what I've been able to tell he doesn't seem to have been particularly well regarded around the league and I don't think it's just down to his recent benching.
A lot of the statistics don't come out very well in his favor as far as fitting in on a winning basketball team is concerned. I understand that his efficiency has improved somewhat but it's still not very good. In November and December SOMEONE needed to score because somebody always has to score on bad teams. It's how you get guys like Gerald Henderson putting up 15 points a game last year. It's not like he could do that on most teams, but the Bobcats were so bad that they depended on him. The same way we depended on Crawford when WE were horrible. But we just ain't looking horrible in the same way we were when Nene and Wall were out, so the team needs are different and the flaws in a player like Crawford become more apparent.
As far as getting better value for him in the trade goes, I think that other teams would look at some of the things around his attitude, particularly the way he has responded since January and proceed with caution. It's like Doc Rivers said, his confidence is both one of his best and worst attributes. And I think that supreme self-confidence is what ultimately led to the problem here. If Crawford really thought he should be starting over Beal and couldn't find a way to try and play within the system, try and become that 6th man then his attitude really was getting in his own way, not to mention the team's. It is telling that Boston was the only team** that contacted the Wizards about him, and that's ONLY because 2 of their guards went out for the season with torn ACLs. Hopefully as he gets older he learns a little more humility, because that just ain't the way to get better.
I've seen a lot of people on here talking about how instead of benching him we should have put him in the shop window and highlighted his good qualities so that we could have traded him for more value… That's a good theory but I don't think it works in practice. The Wizards are trying to develop a team and team chemistry and see what they've got and win some games. They can't set that aside just to play a guy who's NOT fitting into the system and disrupting the team chemistry just to get better trade value for him. Development of the team identity is ultimately worth more than whatever small bump we might have gotten in Crawford's value (which I don't think would have been too much).
Finally, looking around the league it's not like teams were getting great value for these kinds of players. Like at what OKC got for Maynor… NOTHING**. I think that teams look at these sorts of players and think "yeah they're good, but we can probably pick someone up in the 2nd round who can do about the same thing." So as much as we all love Steez, I think we were all over inflating his potential trade value (that ESPN quote about him being the 5th most valuable trade chip aside).
Maybe the team could or should have held onto him longer and just let him keep riding the bench in hopes that a better deal or change in attitude would have come, but knowing what I think I know about it I doubt it would have changed much (for all the reasons listed above) and chances are that his value would not have gotten much better (and having someone like that around the team might have actually made things worse for everybody). At least we got SOMETHING for him (a tiny bit of cap room, maybe it'll help us re-sign Martell next year).
At any rate, I wish him the best of luck with his career and hope he finds great success elsewhere. I don't think he was going to find it here. Ultimately, I'm a Wizards fan more than I'm a Steez fan. So I'm gonna stand with my team.
*Or maybe 2 teams, depending on what may or may not have been discussed with the Mavericks. The official party line is that only one team (The Celtics) contacted the club about Crawford, so I went with that.
** Or practically nothing anyway. They got a TPE. Probably less than they thought they deserved. See this quote from the "Welcome to Loud City" post about the Maynor trade:
"The fact that Presti could not get the 1st round pick he was looking for speaks more to the current CBA landscape than anything else. A year ago? Yeah, that pick might be available. However, with everyone tightening the screws and finally recognizing that draft picks, even low ones, are some of the most sacred assets a team can have, it is perfectly reasonable that other GM's know that giving away a draft pick (and more importantly, a draft pick's contract) is more valuable than dealing it away for a career backup PG."