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Two Complex Sports writers—one Boston Red Sox fan and one Chicago Cubs fan—each wrote a letter to Jon Lester, the highly-coveted lefty free agent pitcher. Early this morning, news broke that Lester chose to sign a six-year $155 million deal with the Cubs, disappointing millions of fans in New England who assumed Lester would re-join the Red Sox after saying things like "I want to be [in Boston] 'til they rip this jersey off my back" as recently as January. Ouch.

In the wake of such a seismic shift in power, our writers decided to give Mr. Lester a taste of what they've been experiencing over the past 13 or so hours since he made his decision. We begin with our resident Bostonian, Doug Sibor:

My Dearest Jon,

I awoke this morning to learn that you really and truly are leaving Boston forever, heading back to the loving embrace of Theo Epstein and his Chicago Cubs. It didn’t seem real. Everything had aligned so perfectly: your great half season before the Sox realized that they sucked, the wink wink trade that sent you to Oakland when we all knew you were going to come back anyway, even your own proclamation last spring that you’d happily take a hometown discount to stay. Everything suggested that on Opening Day next April, you’d be right back where you belonged: on the mound for the Sox in your signature No. 31.

What happened in negotiations? Well, that’s subject to some interpretation. But Jon, I’m not mad at you. Nobody with half a brain is. Not after the cruel joke of a four-year, $70 million extension the Sox offered you in the spring, not after they decided to use your love of Boston as a negotiation ploy, not after this winter when they arrogantly let you field offers from other teams rather than swoop in and blow you away with a huge number right from the jump. No, Jon, the fault here is entirely on your former team. Even at the very end, all they had to do to keep you was bump up their offer by $3 million or so per year and I have no doubt you’d be back. They didn’t, because hey, maybe they need the money to pay Pablo Sandoval’s buffet tab.

The Cubs are a lucky, lucky team. While this era of Red Sox baseball will always be remembered for David Ortiz, you were the rock of the pitching staff. Your stats in Boston speak for themself: three All-Star selections in the last five seasons, 200-plus innings all but one year since 2008, one monumental victory over non-Hodgkins lymphoma, and two World Series rings. You won’t find a single Sox fan out there who doesn’t appreciate what you did for the team, or the manner in which you did it. Your work both on and off the field will be sorely missed.

Now, excuse me while I go cry into my new Hanley Ramirez jersey tee.


Doug Sibor (@dcsibor)

Dear Jon, 

Have no doubt, son, you've made the right decision. As did the Cubs. You're worth every penny of that $155 mil. The time has come to return home to big papi papa Theo. He got you into this league, he raised you to be a champion, and now he wants to make you a legend. Going back to Boston would have been the safe thing to do. That's what you know. That's your first baseball home and you have friends there...but you're not a safe kind of guy. You're a ferocious competitor who cares about leaving your mark on this league. You might be taking a risk by coming to Chicago, but the reward could be enormous. 

Imagine you continue to be the model for consistency. You keep tossing 200-inning seasons, you maintain a sub-3.00 ERA, you fill in the Ace role we all know you're capable of, and you help sculpt the inexperienced squad behind you. I know you're capable. This is your chance to change the course of one of the most perennially depressing storylines in all of sports. Please, Jon, I'm tired of hearing about people blaming Bartman for our team's misfortune. I'm tired of hearing 100-year drought jokes from people who have only been alive for 25 years. I mean, seriously, Jon, I know this isn't directly your fault, but your fanbase has kind of been acting like a bunch of asshats since winning a couple championships. You changed that city's entire demeanor, now it's time to do that for another. 

Besides, don't you kinda sorta want to stick it to Boston after how they treated you? I mean, $70 million? Seriously? They might as well have just offered you stock in Blockbuster Video. I'm not saying use your hate to fuel your focus, but use your hate to fuel your focus (trust, it works really well). 

Anyway, this is all to say, "Welcome." Welcome to the greatest city in the country. Welcome to a city that is now a pitching powerhouse, thanks to you and some other dudes on the South Side (you'll get to know them well). Welcome to the place where PBR, Zippers, and the dishwasher debuted (I mean, c'mon, who likes washing dishes?) Boston might have a giant green wall, but our walls aren't just painted to look that way. Our walls are covered in a beautifully lush blanket of green ivy, and our stadium is home to the greatest hot dog in the world. I know you'll love this city, and I know that you know that I'm counting on you. 

But don't worry, just relax. Take a ride on the Ferris wheel (also born in Chicago) if you want. No pressure. At all. 


Tony Markovich (@T_Marko)

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