I missed this, so maybe you did too. Late last week Pat Lackey of "Where's Van Slyke" wrote this piece comparing Littlefield's trading history with that of the One Red Paper Clip guy.
It's a good piece. The Pirates should do much more trading than they do. They can't win all their trades, of course. But they can make friends and easier trading partners when they get a little less than they could have in a deal.
My point in the Shealy discussion builds on the observation that Littlefield has a history of pissing off the other GMs with his brusque overvaluation of his own players. In addition to this, he appears to only shop the players he wants to trade.
This is too clean to work. It offends. If the team wants to make trades, they have to deal from their strength. You must offer good players to get good players. If we have a surplus in one area - say, two good young third basemen, four good young relievers - those are the players that will best command what we need in return.
There have been studies tying wealth to church attendance. While I would not doubt that God loves his people and rewards them with material goods for attending church, the more practical explanation is the greater amount of barter and trade that church-going households enjoy. Church friend comes over and wires up my new chandelier for free; I give him my old lawnmower, which he repairs into good-as-new condition. We are both more wealthy for the exchange.
The secret to trading is not to leverage some gap in the relative maturity of playters. The strategy of signing old guys for July use as trade bait is a failure. The fact that old veterans are ready to play now, and young prospects are not ready to play now, does not mean that much to contending teams, no matter how desperate they are for the help. This is why Randa, Burnitz, and Casey have so little value.
The secret to trading is getting involved in a circle of people who agree to slosh the resources around. You grab and hold onto what you really need. Everyone is wealthier for it. I would not advocate deliberately losing trades. There is no good that can come from sucking up to other teams in the hopes that they will throw you a reward later. But I would advocate taking more chances. It's the only way to make more trades. The more fluid the flow of players, the more likely it is that the Pirates will be able to assemble the balance of talent they need to compete in this league.
Participating in a more free exchange of talent only stands to increase the wealth of the team. Since they can't afford to buy the players they need, they will have to work on trading for them. And the way to win at trading is to make lots of trades. And the way to make lots of trades is to offer good players in exchange for good players.
This might cause scandal to say, but if I'm the owner of the team I tell Littlefield to dangle Freddy Sanchez. If you are a bona fide professional electrician, you don't offer to paint a picture of your neighbor's wife in exchange for his lawnmower. You must deal from a position of strength to unlock the overstocked garage of that neighbor.
You want to contend and win? Eliminate your areas of weakness. You want one of those top prospects that plays a position of weakness? You offer a top player from your surplus. Of course that could be a PR disaster, dealing Freddy and moving Bautista to his natural position, all to acquire a true centerfield prospect, with maybe a longshot throw in. If the players you select bust, then you are embarrassed. But are you more embarrassed than you would be if, say, your team began the year with 30 wins and 60 losses? I would hope not.