Thanks for the input guys. For the record, the manager auctioning off his team is not sending the players to the same team, but to the second and third place teams. I agree the second trade is worse, and I have to figure out how to deal with that.
The collusion worry is that the team receiving Holliday has a history of trying to convince teams in the cellar to send him top line players for a bunch of bench riders, essentially reverting to the argument that there is no other way to beat the front runner. There are no future considerations in the second trade, either, making it that much worse to my mind.
"The game has a cleanness. If you do a good job, the numbers say so. You don't have to ask anyone or play politics. You don't have to wait for the reviews." - Sandy Koufax