Tony Massarotti

Questions Abound for Both Sox, Lester Amid Breakup

Can the Red Sox just trade the guy and be done with this?

Jon Lester is gone, folks. We said it then and we’ll say it now. For philosophical reasons, the Red Sox simply do not want to pay him. Red Sox principal owner John Henry has made it clear that he deems players over 30 to be unwise investments, and Henry is now digging in his heels. If he had it to do over again, Henry probably wouldn’t sign Dustin Pedroia to that eight-year, $110-million contract that now looks completely unnecessary.

Personally, I believe the Red Sox botched this a long time ago. They had the chance to be more aggressive with Lester in the spring and might have signed him to a five- or six-year contract then. They even could have ripped up Lester’s existing deal - as they did with Pedroia, who is represented by the same agents – and made the package more palatable. They did not. Instead, they low-balled Lester and got negotiations off to a very poor start, putting into motion the chain of events that have brought us to where we are today.

All of that said, there are now a number of questions that remain between now, the trading deadline and well, well beyond.

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* Are the Red Sox now forever averse to big-time contracts for big-time players?

In the baseball world, Boston is a big market. One of the major advantages the Red Sox have over most other clubs is money. JohnHenry.pngThe Sox still seem inclined to use it – the payroll this year is essentially what it was in 2011, when the “high-priced” Sox collapsed in a bucket of chicken and beer, but the Sox are spending it quite differently. The Sox are spreading their money more equitably through the middle of the roster than they are at the top.

It’s as if the Sox embraced the Patriots’ philosophy of doing business … at a time when the Patriots chose to embrace the Red Sox’ methods. (Welcome to Boston, Darrelle Revis.)

In baseball, it certainly feels as if some measure of superstardom is required to win. Last year, for all of the talk about the depth of the Boston roster, David Ortiz, Jon Lester and John Lackey were the best performers in the World Series. The latter came to Boston as a free agent on a five-year, $82.5 million contract. Was that worth it? In retrospect, you bet it was.

* What’s the backup plan if and when the Sox lose Lester?

Please, no talk of loyalty, paying for past performance or emotional attachment. We are all way, way past that. If the Sox had a replacement-in-waiting - and maybe they do – none of us would care as much. For example: some of you are still lamenting the loss of Jacoby Ellsbury, who is batting .282 with a .752 OPS for the New York Yankees this season. Many of us haven’t given a second thought to Ellsbury’s departure, largely because the Sox had Jackie Bradley at the time and because Ellsbury simple isn’t worth what the Yankees are paying him.

But Lester? Minor league left-hander Henry Owens looks like a stud in the making … but so did Bradley. And Xander Bogaerts. The reality is that most young players need time to adapt to the major leagues, and a team like the Red Sox should be able to integrate a kid like Owens on a staff with veterans like Lester and Lackey as glue. As we’ve learned with the positional roster this season, too many young players at one time leads to inconsistency and poor performance at the big league level – and may damage the development of young players.

The free agent market is thin. Even if it weren’t, the Red Sox clearly have an aversion to paying anyone free-agent dollars. Hamels.pngCole Hamels might now be available by trade, but does it make sense to trade prospects and pay Hamels a guaranteed $96 million over four years (with the chance for more in a vesting option) when the Sox could have just paid Lester and kept the prospects to improve their offense?

At the moment, the Sox seem more interested in the contract than the player. Let’s say the Sox could essentially execute a three-way trade in which they swapped Lester for prospects, then swapped prospects for Hamels. (Essentially, that would be a Lester-for-Hamels swap, right?) Sox supporters might celebrate that as a major victory, even though Hamels raises other questions, most notably his relatively poor performance against American League competition.

Why not just may the known commodity?

* Why isn’t Lester under greater scrutiny?

Fact: the Red Sox stink at the public relations game. John Henry communicates only by email. Larry Lucchino comes off as sneaky. And no one believes that TV producer Tom Werner has any real juice (or knowledge) on baseball decisions. Meanwhile, Lester acts humbly and deferentially, saying first that he would take a hometown discount and then that he would still re-sign here even if the Red Sox dealt him.

In the court of public opinion, this has been an epic blowout.

But amid all of that perception, there must also be some reality.

If we’re going to be fair about this and if we are to believe what has been written, why hasn’t Lester’s camp been more engaging in talks? Lester0730.pngAccording to the Red Sox via their “industry sources” network, caricature agents Sam (good cop) and Seth (bad cop) Levinson never presented a counteroffer to the four-year, $70-million proposal the Sox put on the table in spring training. Why not? If Lester truly wanted to remain in Boston, shouldn’t he and his agents put aside all petty nonsense and earnestly negotiate? So why haven’t they?

Because Lester wants his money, that’s why. And just as the Red Sox saw an opening to exploit Lester after he first spoke of a hometown discount, Lester and his agents saw an opening to exploit the Red Sox when they came to the table with less money than they gave an older John Lackey four years ago.

Since that time, of course, the market has exploded. The annual installment of national TV money issued per team has doubled from roughly $25 million to $50 million annually. (This is free money for the Red Sox.) Lester certainly has a right to be paid as one of the best pitchers in the game, it seems terribly disingenuous to talk about how much he loves it here while his agents won’t engage.

The Red Sox, to their credit, have commented openly about the state of negotiations. Meanwhile, Lester’s agents have been whispering only through back channels as Lester has said that in-season negotiations would be a “distraction.”

Is that really the case? Or are Lester and his advisors merely flexing their muscles in the wake after what they deemed a low-ball offer?

Lester can’t have it both ways. He can’t say he would take a hometown discount and then fail to engage in talks because the initial offer was too low.