Adam Kaufman

Ruling out Jon Lester’s Return to the Red Sox Would be Premature

The Red Sox made more efforts in two days last week to inform the media that contract talks with Jon Lester had been tabled until the offseason than the organization has attempted to actually sign its ace as he inches closer and closer to free agency.

First, owner John Henry sent an email to the Boston Herald on Wednesday, saying, “I’m not going to discuss Jon’s situation out of respect for both Jon and [general manager] Ben [Cherington] other than to say that both sides have put further discussion off until after the season. It’s clear that both Jon and our organization would like to see Jon back next year if possible.”

By the time the note was published on Thursday morning, Boston CEO Larry Lucchino was firmly confirming that message in an appearance on WEEI’s “Dennis & Callahan” program.

“I’m not going to answer a question about the analysis of the stages of this negotiation, because the negotiation will continue,” Lucchino added. “It will continue after the season, to be sure, but there will be an opportunity for us to resume negotiations with Jon and with his agent — they have made that abundantly clear to us. So, looking back and doing an analysis of, ‘Was this a wrong step or was this the right step,’ would only be counterproductive.”

No matter; that left plenty of time on Thursday for many in the media to weigh in.

The consensus from the masses were a varied and familiar tune, from analysis over just how badly the Red Sox screwed up this negotiation dating back to a reported four-year, $70 million insult of an offer in the spring to a demand Boston deal its top pitcher by the MLB’s July 31 trade deadline out of fear he’ll simply walk for nothing more than a compensation pick. And who could forget the club’s rumored pursuit of the Phillies’ Cole Hamels as a leverage tactic?

Spinning Lester off to a contender like the Dodgers for an injury-plagued bat or a top-tier prospect or two might very well be the safest route at this point, but it would also be premature.

Throughout the year – the best of Lester’s career in his nine big league seasons – the southpaw has said and done all of the right things, all the while keeping his personal thoughts very close to the vest. As the Boston Globe’s Dan Shaughnessy wrote earlier this month, Lester has handled this situation perfectly.

Unlike how David Ortiz’s seemingly annual cries for more money have been met with threats of leaving the city that put him on the map if he wasn’t handed the proper amount of monetary "respect," Lester has never once indicated a desire to leave the only home he’s ever known. Not for one fleeting moment has he been a distraction. Frankly, he’s been a role model for any player in his situation.

There will certainly be suitors, whether from our friends in the Bronx, his hometown of Seattle, the financially-flexible teams in Los Angeles, a team in Detroit (should it lose out on Max Scherzer) eager to win again as soon as possible, or even a mystery club with deep pockets. Lester knows, barring injury, he’s setting himself up very well to be paid quite handsomely, but he also openly prefers his familiar red socks.

At one point, the lefty could be heard practically begging to take less in order to stay. That tune has changed in a monetary sense, but his hopes of continuing to call Fenway home have not.

Like with anything, we can debate which side actually put a halt to the talks. We’ve been led to believe by Boston brass that it is Lester’s camp that’s unwilling to negotiate until season’s end.

However,’s Rob Bradford filed a report Thursday morning that was counter to that message, stating. “The pitcher would be open to an in-season offer that was consistent with the marketplace,” according to an industry source.

Bradford continued, “If the Sox were to make an offer in line with what the market has produced in terms of recent contracts for pitchers of Lester’s status, the source added, such an offer would permit an efficient resolution as to whether the basis for an in-season extension existed, thus avoiding concerns about potential distractions for either the pitcher or his teammates.”

In other words, the deal could be done – even in the face of some in-season distraction – if the Red Sox stop screwing around and make a real offer.

Industry experts have speculated Lester could command anywhere from $120-180 million dollars on the open market, depending on the length of the pact. There are those who believe the Sox are unwilling to offer beyond four years after being burned by previous high-priced, long-term deals with Adrian Gonzalez and Carl Crawford, while the early returns on Dustin Pedroia’s extension have been less than favorable.

Henry also hasn’t hesitated to point out in the past that players tend to regress dramatically on the wrong side of 30. Lester will be 31 on Opening Day in 2015.

There’s no arguing the Red Sox have messed this up. They likely could have gotten a deal done before the season for something in the neighborhood of five years and between $100-120 million. Their lowball, look-at-how-smart-we-are tactics in the offseason, coupled with Lester’s unfazed dominance on the bump has landed them here, a few months shy of losing their most durable rotational arm for virtually nothing.

Still, I strongly believe all hope is not lost. Call me an optimistic, but I think Henry and co. could still offer five years with a respectable average annual value (likely about $25 million – probably $5 million per year more than it would have taken a few months ago) and lure Lester back to Boston, even if a potential new destination would stretch itself by a year or two.

Lester, based on all reports and the way he’s carried himself to this point, feels that strongly and committed to his baseball roots. He’s said time and time again he isn’t interested in change.

At 10-7 with career-bests in ERA (2.52), WHIP (1.119), strikeout-to-walk ratio (4.66), and walks per nine innings (2.0), Lester’s price-tag is rising with every start. He's a two-time World Series champ, a three-time All-Star, and a proven commodity.

Lester owes it to himself to test free agency and attach a dollar-figure to his resume, but it would be foolish to rule out his return to the Fens for fewer overall dollars so long as Boston’s next offer – if there is one – isn’t so wildly off-base and out of touch.

The pitcher said it himself, telling the Boston Globe’s Nick Cafardo, “There’s been plenty of guys who have taken less to come back. Mikey Lowell had more years and money with the Phillies and he came back. [Tabling contract talks isn’t] the end all for everybody. I’ve expressed to [ownership] I want to be here.”

Lester isn’t the mercenary former teammate Jacoby Ellsbury was last winter; his ticket out of town hasn’t already been punched. He doesn’t possess the over-the-top bravado of Ortiz; he won’t call himself one of the greatest to ever wear the uniform while chasing every last dollar available to him. Off the field, he’d prefer to blend in.

Now, it’s personal. If Lester does leave, that decision will be equally based in emotion to economics. Loyalty is a two-way street, just as it is to feel wanted.

We believe we know what Lester wants, but how about his team? If the Sox want to continue to play the role of short-term contract exclusivity then, by all means, trade Lester and continue building that next good team we keep hearing about. But if they wish to retain their star, all hope is not lost – so long as they approach their next discussions with the level of respect they repeatedly claim to have for him.

Follow me on Twitter at @AdamMKaufman

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