Touching All the Bases

Jon Lester Was Everything a Red Sox Player Was Supposed to Be — So Why Is He a Cub?


To become one of Our Guys, to gain induction into that exclusive club and count among that class of Red Sox player beloved during his playing days and remembered reverently long after his final innings, certain criteria and characteristics are common if not outright requirements.

The easiest way to win us over is to .... well, win. Many with lasting legacies have contributed to a championship team (or two ... or three) or performed valiantly in defeat (Yaz's entire postseason catalog).

Humility, or grace under pressure and beyond, no matter the outcome, is admired. But we also dig confidence, even if for comical (Dustin "Ask Jeff Francis Who I Am" Pedroia) or cartoonish (Kevin "That Was Not A %*(#) Strike You Stupid %*#* Blind #(#*@ Ump!" Youkilis) effect.

Appreciating Boston -- hell, getting Boston, digging Boston, and thriving in this distinctive atmosphere -- matters to us.

So does overcoming adversity -- and helping others overcome adversity, whether through the franchise's indelible ties with the Jimmy Fund or in another charitable, personal way.

We appreciate watching players grow up here, to enjoy the entire shape of a career, which is why it's so cool if you're homegrown, someone became familiar to and with Red Sox fans during the journey from Lowell to Portland to Pawtucket to 4 Yawkey Way.

Fulfillment of all of the criteria is not required to become one of Our Guys. Pedro was a gift from Montreal via Los Angeles. Manny (well, he's one of my guys, if not everyone's) and Eck began their ascents in Cleveland. El Tiante did too. Freddie Lynn left for sunny California, Pudge put in more seasons with those other Sox, and Dewey even had a did-that-really-happen? final season in Baltimore.

None of that prevents the cheers from cascading when they wave down from the EMC Club after their personal highlight reel plays on the Fenway video board. Forgiveness is just a nostalgic flashback away.

I realize I'm treading embarrassingly close to, if not full-on beyond, True Yankee territory here. So be it. I'm OK with that, because fans of any franchise (even the Rays, maybe?) care about these things, about legacies and history and traditions passed from one generation to the next.

The reason I am jabbering on about this now should be apparent. LesterWatch, our long New England nightmare of waiting nervously for Red Sox-turned-A's-turned-coveted-free-agent Jon Lester to choose his next baseball home, is over.

It ended in the dark hours as last night turned into this morning, and it sure as hell wasn't worth waiting up for if you're a New Englander. Lester chose the Cubs, and Wrigley Field, and Joe Maddon, and yes, Theo Epstein and Jed Hoyer too, agreeing to a six-year, $155 million deal with a vesting option that could bring it to seven and $170 million.

He also chose the best offer, at least in comparison to what the runner-up Red Sox pitched. According to multiple reports, the Red Sox' bidding topped out at six years and $135 million with no option.

If you can get past the mind-numbing wonderment of the Red Sox being a runner-up to the Cubs in something, there is only one conclusion to draw: This sucks, and for a lot of reasons.

Baseball-wise, those reasons remain the same. The Red Sox still need two top-of-the-rotation starters. They just lost out on their first choice, the familiar choice. The cost -- in cash and prospects -- is going to be steep, and everything else feels like Plan B now. You hope the fallout from this doesn't lead to them doing something foolish.

But the longer-view, visceral reason this sucks?

Because Jon Lester is one of Our Guys.

Always has been, always will be, even as his Red Sox ties are suddenly in the past tense. He is the rare player who fits all of the aforementioned criteria. He's the quintessential qualifier.

He was confident, overcoming an early-career predilection for letting a bad call affect him to become an ace whose stoic veneer cracked only after the recording of a crucial out. Then he would pump his golden left arm in celebration once, maybe twice, high-five a teammate or two, then put his stoic mask back on before the new inning began.

He was homegrown, having been drafted in the second round in 2002 during the general manager transition between Dan Duquette and Theo Epstein. He was nearly dealt to the Rangers in the blessedly nixed Alex Rodriguez blockbuster in the winter of 2003, then ascended through the organization with a heady class of talent -- Hanley Ramirez, Dustin Pedroia, Jonathan Papelbon, Anibel Sanchez, Brandon Moss and David Murphy were teammates along the way . He arrived in Boston in June 2006, winning his first five decisions. He departed in July 2014, having won 110 games, ninth-most in franchise history and second among lefthanders.

He won championships here, plural. In 2013, he was the genuine ace, winning four of his five postseason starts and putting up a 0.59 ERA in the World Series. In 2007, he was the comeback kid, winning the title-clinching Game 4 with 5.2 shutout innings just four months after returning from a fight with non-Hodgkins Lymphoma.

Adversity? This is a man who overcame true adversity. We're not talking about just the trite and trivial baseball kind, such as his aberrational, lousy 2012 season, or even the self-inflicted embarrassment of the 2011 Summer Of Chicken 'N' Beer, though it's a tribute to his character that he learned from silly mistakes and genuine struggles.

We're talking about one of the most terrifying words ever spoken: cancer. In August 2006, Lester began feeling pain in his lower back. It was believed to be related to a car accident he had been involved in on Storrow Drive, but he later acknowledged it had been bothering him in the weeks before the crash. He went to see his personal doctor in Seattle. The diagnosis was shocking: Lester, just 22, was informed he had anaplastic large cell lymphoma, a highly treatable form of non-Hodgkins lymphoma, but one that often spread quickly. He began chemotherapy treatment almost immediately.

During his treatment, recovery, and gradual, eventually triumphant return, our perception of Lester changed. He was no longer just some strong, gifted athlete who earned our cheers every fifth day. He was as human as we ever knew him to be and a symbol of something larger at once. He was relatable, a reminder that cancer does not play favorites, that it can affect everyone from your favorite lefthander to your favorite uncle. He could not hear us, but we cheered for him more than ever.

In the aftermath of winning the clincher in '07, cameras caught him in a couple of beautifully candid moments. In one, he's hugging his dad while he mom beams. In another, he's smooching his girlfriend (now wife) Farrah. One prop is present in both photos. The World Series trophy. But that's not what you're looking at. You're looking at the pure joy of a family.

Authentic, genuine scenes like that, or like Terry Francona's fatherly embrace after Lester's no-hitter in May 2008, jostle our emotions and linger in our memories. Lester is an important thread in the fabric of Red Sox history, a first-ballot Our Guy who undeniably met that final criteria: A love for playing here and an appreciation of the experience.

Oh, sure, Lester is going to take some heat now. A lot of it. But taking passion, fandom and hurt feelings out of it -- I know, good luck with all of that -- I don't know how we could ask him to say no, especially given the wide discrepancy in the offers. The Cubs made him a virtually irresistible proposal -- an insane one for an almost-31-year-old pitcher, really -- and he accepted it.

Still, you know how this works. The most scarred among us won't take this well. We're almost certain to hear thinly veiled frustrations coming from the Red Sox side on how negotiations played out. He'll be called a traitor and a hypocrite and he'll be reminded about his frequent comments about his desire to remain in Boston, most notably these from the Boston Baseball Writers' dinner last January:

"These guys are my No. 1 priority,'' Lester said those 11 eventful months ago. "I want to be here until they rip this jersey off my back.

"I understand that to stay here, you're not going to get a free-agent deal. You're not going to do it. You can't. It's not possible. You're bidding against one team. I understand you're going to take a discount to stay. Do I want to do that? Absolutely. But just like they want it to be fair for them, I want it to be fair for me and my family.''

He wanted to be here. He said so, then said so again. So why did Our Guy go?.

Because circumstances changed. And circumstances changed because the Red Sox allowed them to -- even encouraged them to. The four-year, $70 million offer in the spring, a time when Lester was on record as saying he'd hoped to get a deal done, was a lowball offer by any measure and in any context.

That allowed him to consider, to really consider, the possibility of playing elsewhere.

Then they actually sent him elsewhere, trading him to Oakland at the July 31 trade deadline. This gave him first-hand knowledge that while the grass may not necessarily be greener, his baseball universe doesn't have to begin and end within the confines of Fenway Park.

Then, after a star-turn in Oakland, he hit free agency during a perfect storm of a market in which all bets were off and multiple offers and destinations were appealing. Once you get to free agency, especially if you live the perilous life of an MLB starting pitcher, why not enjoy it? The Red Sox had already traded him to one elsewhere. What's wrong with considering one or two more?

This was his prerogative, and the Red Sox made sure he followed it.

Do not listen to the apologists who will tell you Lester misled them, that it was about the money all along. This was a Haywood Sullivan-level bollixing by the Red Sox front office. This is on them.

Lester said he'd take a discount. They heard that and promptly tried to get not a discount, or even a bargain, but an outright steal. Lester heard that $70 million, bet on himself, and more than doubled his money. Had they begun negotiations with a good-faith offer -- say, five years and $90 million, with an acknowledged willingness to negotiate, he'd still be here.

Instead, he's gone, again. This feels so much different than the trade. It's far worse. This feels like they lost him, like this is the last goodbye.

It's not, of course. He accomplished too much during his eight seasons with the Red Sox to become persona not grata. And it's not like he signed with the Yankees, though the defection to Theo's Cubs -- is that a chortle we hear coming from Chicago? -- will certainly rankle Larry Lucchino.

Someday, Lester will say hello again. It's just too bad it will happen in a ceremonious moment, a first pitch before World Series game in 2027, or a wave from the EMC Club a dozen years from now.

Most Red Sox fans were hoping for a happy reacquaintance the day pitchers and catchers report to Ft. Myers. But the reason he won't be there this spring, why he's an Our Guy on hiatus, is because of what happened last spring.

The Red Sox tried to take advantage of his spoken desire to stay. As it turned out, they were just beginning to drive him away.

Continue Reading Below

More from this blog on: Red Sox/MLB