Insider of my trying to comment on/summarize this, you really should just read Buster Olney’s column on ESPN.com; it’s great. Here are some pertinent sections:
“‘If I represent you,’ [Boras] has told some players in so many words, ‘only I do the negotiating.’ Their impression is that he wants 100 percent control. ‘Why would I do that?’ one player mused, looking back on the day that Boras tried to sign him as a high school senior. ‘It’s my life.’ When Boras negotiates, club executives sometimes wonder whether all the facts — whether every piece of every offer — gets through to the player. They never know, and it scares the hell out of them; Boras is the funnel through which all the information is channeled. This is why Theo Epstein and Larry Lucchino flew to California late, why they rode on John Henry’s private plane, why they’ve become so open and outspoken about their negotiations.” …
“And you’d have to wonder: For Scott Boras, when does this stop becoming a chase of dollars and start being about his clients’ doing what they love in their work and playing baseball?” …
“Matsuzaka has never pitched a day in the major leagues, and it could be that when Boras is finished haggling, the pitcher could make $10 million in his first year in the majors, and more after that. Much more.
But with every passing day, with every delay, with every insistence upon more dollars, Boras is effectively placing more pressure on the shoulders of his client, who already is facing an enormous adjustment if he signs to play in Boston. And if Boras/Matsuzaka don’t sign, if the agent’s filibuster continues and they try to make the pitcher the Curt Flood of the Japanese posting system, you have to wonder whether it really will be worth it, in the end, for Matsuzaka.”