Here is what I see in those trades... you gave up a lot of future contributors and took on a ton of salary for a chance to try to win now, but you aren't set up to win now.
I didn't think they were that bad either...The one sequence that will come back to bite you is
In the
Player Profile: Gaylord Shiell - Hardball Dynasty Baseball | WhatIfSports trade, you got back some useful offensive players, but gave up a #1 type SP. He wont be ready for a couple of years, but that is a very valuable guy. I actually didn't think this trade was too bad when I got to Engel Nunez. I might not have made it, but I think its defensible. Shiell looks like the kind of pitcher who is not easy to acquire, especially if you don't pick at the top of the draft or pay way too much for him in FA.
and then you went and traded Engel Nunez
Player Profile: Engel Nunez - Hardball Dynasty Baseball | WhatIfSports ... I don't think he'll ever be a great catcher, but he's a hitter who can help you...in return you got an older, worse version of Shiell, with the added detriment that hes going to hit his ARB years next season. I would have rather had Shiell in my MLB rotation than Michaels.
In the end, you gave up a very good future SP for a bunch of right now JAGs (just another guy). I would have rather used that money elsewhere (like IFAs) to build your team up for the next couple of seasons while your recent 1st rounders make their way to the bigs. As it is, you have now traded basically the top part of every draft your world has had, and in return you have gotten back older, more expensive players who will make your team a little better right now and worse in the long run. I think you just misjudged where your team was at in its development cycle and tried to load up on vets when you should have been building on the minor league guys coming up. You're hardly the first person to make this mistake.