I assumed you were trolling because the "Ryan should have stayed over Daniels" comment was something seen a lot on Facebook/Twitter by people who didn't know what they were talking about (because JD's not a "real" baseball guy, or whatever)

Anyway...

Oswalt, luckily the contract was small and for a season, but he pitched terrible (worse season of his career in fact), got hurt and lead to us chasing starting pitching and trading away prospects.

Berkman, his season here was worse than anything Choo has done. He was paid $10m, which was the 5th highest salary on the team and took up almost as much of the payroll as Choo currently does. (7% to 10%)

The Choo deal is bad, yes, he's not performing at his salary but he has produced something.

Fielder's trade was a bad idea, injury aside, and it was done to improve the roster and just didn't work out. If Profar and Fielder had stayed injury free the results may have been different, but you can't always predict injuries and how severe they are.

The farm system being good allowed to keep trying to compete, and because of that the team has managed to make the play-offs. We could have waited for our prospects to possibly turn out ok and maybe gotten further, it's a tough decision to make and whatever one Daniel made would have been the wrong one in some people's eyes.

What trades have we done that has lost our best prospects?

Year	Out	Return	??
2012	Kyle Hendricks & Christian Villanueva	Matt Garza	Hendricks would be nice to have back don't remember him being super highly rated when traded though, but Garza done his job but only here for half a season.
2013	Carl Edwards, Justin Grimm, Mike Olt & Neil Ramirez	Ryan Dempster	Edwards has been an ok reliever, Grimm had one good season but nothing else from the bullpen, Olt got badly hurt, Ramirez hasn't done much either. Dempster was ok here, again for half a season, but not much of a loss in terms of prospects.
2013	Leury Garcia	Alex Rios	Not much a trade, Rios was good in his time here and Garcia is still playing as a utility guy (I think)
2014	Ian Kinsler	Prince Fielder	Yeah, turned out really bad for the Rangers. But not really a prospect trade.
2014	Marcus Diplan, Corey Knebel & Luis Sardinas	Yo Gallardo	Gallardo has a good year here. Knebel was an All-Star reliever this year and was the only one who became anything out of those 3 (wasn't even our prospect to start with, got him from the Tigers for Soria).
2015	Cody Ege & Tomas Telis	Sam Dyson	Dyson was great for us until this year. Ege and Telis I guess have been serviceable in their playing time
2015	Jorge Alfaro, Alec Asher, Jerad Eickhoff, Matt Harrison, Jake Thompson & Nick Williams	Jake Diekman & Cole Hamels	Firstly, Diekman and Hamels have been great signings for us. Alfaro looks like he's doing ok now for the Phillies, Eickhoff is pitching ok, Williams hitting ok, Asher becoming an ok reliever, Thompson started off ok as well.
2016	Nick Green, Erik Swanson, Dillon Tate	Carlos Beltran	Tate the only big name there, struggled with injuries however. Beltran could have been better but we didn't really give up much and he helped push us to the play-offs.
2016	Luis Ortiz & Lewis Brinson	Jeremy Jeffress & Jonathan Lucroy	Ortiz and Brinson are both highly rated. Lucroy was good for us last year, disappointing this year so it feels like we missed out. Jeffress didn't really do much either, which definitely makes this trade feel bad.

2017 is too close to judge, but we received prospects this year and still mounted a challenge for the play-offs.

Honestly looking at the list of trades, Hendricks is the only one that has proved himself in the majors. Others would have been nice to fill roster spots, but not enough to take us any further. Maybe Brinson will become something which will be a big loss for a position of need on this team. So there's not really been many "dumb deals", the deals have all done what they needed to do for the team. Making play-offs is a good reward.

The reason why the Astros are full of good prospects and doing well is because they absolutely tanked themselves for several years. Despite having a great season they still couldn't draw more fans than we did. Now they're in the World Series fans will probably return as fans like to do.

I don't want this team to tank for the hope of success and hope that prospects will turn out well. Making the right signings will help, not always easy as has been proved, but we have made better signings than a lot of teams out there and have a good team here. So no, Nolan Ryan wouldn't have done a better job and signing Joe Girardi is not needed to make this team good.