When Jay Bruce declared from the draft from high school, he selected Scott Boras to be his agent. He was told by several scouts that because of this, many teams would not select him. Bruce promptly switched agents.
Kenny Williams also refused to deal with Scott Boras for a long time, even going so far as to trade away several Boras clients already on his roster...
I don't think that the Sox should get into a bidding war with another team. They should already have in mind what they think JD is worth, and not go above that limit. Theo operated that way. I'm not sure that Dombrowski does.
At any rate, I hope that Dombrowski has asked Boras to give him a chance to beat any offer given to JD before allowing JD to sign with another team. Not that Dombrowski should necessarily beat said offer, but at least give him that courtesy in case the other offer is not crazy.
In terms of being a good agent, I think Boras should play teams against each other and I think that he should ask other interested teams to top it. He should be trying to get the best offers he can get, then let his client decide which one he wants.
I don't think the Sox should tell Boras that they'll top any offer, but I think the Sox should ask Boras to give them that chance.