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As noted, the Cubs must compensate the Red Sox, just as the Florida Marlins compensated the Chicago White Sox when they signed away manager Ozzie Guillen. This is standard protocol when a non-player with time remaining on a contract changes organizations, which leads to an obvious question: why on earth are these moves happening at all?
No manager is worth an everyday player in a trade setting. The Marlins gave up only two fringe prospects in order to get Guillen, and that seemed an exorbitant cost. Almost universally, managers are poor tacticians, rigid thinkers and have varying (but immeasurable and unpredictable) impacts upon team chemistry and individual player performance.
Of course, GMs are a different case. Player acquisition and organizational philosophy are critical components of success. Even if deployment of resources matter fairly little, the quality of those resources (i.e., the caliber of talent consistently flowing into an organization and onto the field) matter a great deal. The work a GM does is crucial, and GMs are very different in their abilities to handle their mission-critical duties.
Relying on a GM’s own acumen at every turn in this massive process, though, is to invite disaster. No one person should be making all the decisions about which players to bring aboard, let alone other choices about where to spend money and where to send key assets.
More importantly, an owner should not have a vague idea of how they want their guy to go about things. Only a certain amount of trust honestly needs to be placed in those executives. The information one needs to build a consistently competitive, profitable and upstanding team is objective, and much of it is freely available.
Theo Epstein has done very well at his job, but 100 people who have never had the chance to do similar work could do it just as well. Trade skills—the ability to consistently get the better end of deals with other GMs, and to sign free agents for less than their true value by negotiating well with player representatives—are arguably the only demonstrable skill inherent to any one candidate, and paying handsomely for anything but that skill set is folly.