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I like your analogy, but Boras faces a much more difficult situation.  In golf I believe that many times there isn't a lot of uncertainty about the club only the execution.  In Boras' situation, both are unclear.
Let's look at some data.  Albert Pujols made $14M last year while Texiera made $21M, even though Pujols is a far superior player -- by the tune of 9.5 WAR over the last three years.  Pujols could probably be earning $10-15M a year more if he had gone to free agency.
If could quite possibly be that the cost of not having the Pujols of the world go to free agency exceeds the cost of having someone get hurt before they reach free agency.  An oft injured, but talented, player like Nick Johnson still get $4-8M a year, so the cost is mostly in contract years.