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Acquired RHP Jesse Crain from the White Sox for future considerations. [7/29]

This is not your normal deadline trade. For starters, Crain is on the disabled list, dealing with a strained throwing shoulder. His last attempt to get back on the mound didn't go so well, giving his short-term outlook an ominous feel. But the Rays are not the only team invested in Crain's health. The White Sox, led by Rick Hahn, have creatively put their return on Crain's right shoulder. If he gets back soon then they'll receive players to be named later. If he doesn't then the White Sox will likely receive cash. Hahn and Andrew Friedman have, in a sense, pulled off a trade-and-follow.

The Rays should be happy with their deal if Crain gets back to normal. Crain is a hard-throwing right-hander with a deep arsenal—including two breaking balls and a seldom-used splitter. His mechanics contain the right amount of funk, with bow-and-arrow-like arm action and a high three-quarters release point. Because of the deception and velocity, Crain is able to pitch up in the zone and live to tell about it.

Presumably the Rays would add Crain to an impressive end-game group that already features Fernando Rodney, Joel Peralta, Jake McGee, and Alex Torres. Add in Jamey Wright and it has the look of a strong unit to finish out the season with. If those pitchers are staying then whom might Friedman shed? Perhaps no one. The Rays are notorious talent hoarders, and always seem to stretch a 40-man roster further. Were the Rays to cut ties with a reliever expect it to be Kyle Farnsworth; unless, of course, they put him on the disabled list with a well-timed strained forearm.

UPDATE: So much for the contingency part. Ken Rosenthal reports the White Sox and Rays will decide on the return independent of Crain's performance. It's still a bit of a trade-and-follow, just one not directly related to Crain.

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Who decides what level of talent is appropriate to strip away in from the purchasing club in PTBNL cases? What if the Rays refused to submit a product the White Sox see as fit for a return? What mechanism is in place in MLB to insure that the Rays don't just send their very worst relief prospect or something? Or does the fact that there are only 30 GMs ensure that if you acted like a dick with PTBNL cases you would be ostracized from the trade community immediately? Who knows, GMs are weirdos.
Typically the teams agree on a list ahead of time. So the Rays submit a list of 4-5 guys they're OK with losing, and the White Sox scout them and pick one.

I don't know if this is a typical deal but that's how it usually works.
Also, I imagine that if they couldn't agree on compensation, they could probably go to arbitration, either with the league office or someone independent, kind of similar to how salary disputes work.