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Let's look at your point in two parts: Paying a player "above market compensation" refers to the going rate of his expected performance. The player still has the opp'y to make good on this premium by outperforming expectations. As I said in the example of Millwood (Rangers). The Rangers overpaid, based on reasonable expectations about his performance, but then he over-delivered, even when measured against the premium. So, I wouldn't leap to "if he is paid more than the market rate (at the time of the contract signing), it's bad for the team"
Not sure. It would depend, in part, on the % of the free agents that allows geography, club loyalty, pennant prospects to trump dollars. You seem to imply that the Boras-type client is the minority. I'd like to find a way to test for that--player motivation--because it's not obvious to me that his clients are outside the norm. In other words, if 100% of Boras clients are income maximizers and 90% of non-Boras clients are income maximizers, then this is not a big issue.
I would agree with your first premise--if you are not an income maximizer, you probably don't want/need Boras, like when Kenny Rogers broke ranks to stay with the Tigers.
Tango's point is definitely valid. One option may be to count 6 x $16 as the equivalent of 7 x $14.4, using the rule of thumb that I've seen Tango use in the past, where each additional year is worth a 10% decline in AAV. Then Boras 7 x $18 is $11.2 million more than the average agent (7 x $1.6 more per yr).
The pitching contracts "in progress" besides Zito are Derek Lowe, Rafael Soriano, Mike Gonzalez and Bruce Chen.
On Lohse's 2008 "valuation", when you rack up all the pitchers that signed one-year deals for that season, and look at how they actually performed in 2008, it cost teams $6.6 million per WAR, on average. So given the peer group that Lohse was part of for that one season. To buy his 3.1 WAR from that pool of free agents, a team would have paid $20.5 mil, on average.