It is never best to pursue a Scott Boras free agent early. The earlier a team pursues a Boras free agent, the higher Boras' demands are. Boras will always start with a demand of ridiculously high money for ridiculously many years for one of his free agents. If you want the Sox to sign a Boras free agent, it's best for the Sox to wait for Boras to reduce his demands. Boras reduces his demands at a snail's pace, so this wait requires a lot of patience.
Another reason not to pursue a Boras free agent early is because of what happens if that early pursuit includes making an early offer. The earlier the Sox make an offer to a Boras free agent, the earlier Boras negotiates that offer with other teams to get higher offers from other teams.
I know these first two paragraphs might look like they contradict each other, but they don't. For example, suppose Boras demands 8 years for $25 million a year to sign his free agent who you feel is worth 5 years for $16 million a year. Now suppose the Sox pursue early and make an early offer because they want Boras to give in. Let's even say it's a generous offer of 6 years for $20 million a year. Now he can go to other teams and try to get teams to top it. If at least one team tops it and the Sox still want to sign the player, now the Sox have to beat that higher offer to do so. Then Boras can continue to work teams against each other to raise the price and/or years.
On the other hand, suppose the Sox wait for Boras to lower his demands for that player. Boras won't have as much* success working teams against each other because he'll have less and/or lower offers to work with. Eventually, and I can't emphasize enough that it requires a lot of patience, the Sox will be more likely to* be able to sign the player for less money and/or years than if they pursue him early.
*Please do not misinterpret these sentences as though the words in red aren't included. I'm not saying that waiting means the Sox will be able to sign a Boras free agent without drastically overpaying or that they'll sign him at all. I'm only saying that waiting improves their chances. Usually I don't get my hopes up about signing a Boras free agent at all because of 1) this and/or 2) whoever signs a Boras free agent will likely overpay in both money and years to do so, regardless of how that team approaches its efforts to sign him.
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One of the things I don't get is why some SoSHers act like they're on NYYFans. For years, we would complain about stupid Yankee fans and how they would post about what top free agents they should sign, or that they should sign someone they don't have room for and then just trade so-and-so to make room. That is what the "sign Tex" at whatever cost amounts to. So we should "Sign Tex" (regardless of the exorbitant cost), and then just trade Lowell. Simple right? No mention of how that would play in the clubhouse, or even that it might be difficult to trade Lowell until he proves he's healthy, or anything like that. Just does not seem realistic IMO.
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