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There is absolutely no way that Boras will even consider a contract extension. Boras' number one rule, the Prime Directive that any player must agree to if they are going to hire him, is to go free agency as soon possible. That is where he can work his magic and secure a monster deal. Boras doesn't care one iota about how that might inconvenience the execs in Detroit, they mean nothing to him. He also does not "play it safe" by postponing free agency in exchange for guaranteed money. He wants to get the biggest deal possible, and that means getting his guy into the market at the youngest age possible, regardless of the risks.
One thing to keep in mind is that Boras is probably not motivated simply by a desire to make the most money for himself. He seems to genuinely hate the teams and be driven to make signing his clients a truly painful experience. He somewhat reminds me of record producer Steve Albini. Albini will work with artists signed to major labels, but will deliberately demand an exhorbinant price simply because he has no respect for the big record companies. Boras is likely similar. He probably thinks that the players deserve a far larger cut of the revenue stream and that the teams are essentially screwing the players so he is not going to accommodate them in anyway. If anything, he wants to make the baseball executives miserable. (This is why I could not fathom why anyone thought that Bavasi could work out more favorable deals with Boras clients because of some relationship the two might have even if such a thing were even ethical, which I don't think it is.)