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Jon Lester buys into dream of helping Cubs end World Series drought

The doorbell rang at the Sharpsburg, Ga., home of Jon Lester one day last week. When he opened the door he saw standing there Giants president Larry Baer, general manager Brian Sabean, assistant general manager Bobby Evans, manager Bruce Bochy and catcher Buster Posey.

The first one to speak was Posey, who lives 134 miles south of Lester. Posey reached out his hand and said to Lester, "Hi, I'm Buster Posey. I want to be your catcher for the next six years."

Yesterday Lester told the Giants, "Thanks, but no thanks." His rejection of San Francisco included a separate call to Posey. Lester turned down the chance to pitch for the team with three World Series titles in the past five years, a string of sellouts in the best ballpark atmosphere in baseball and — this is what any pitcher aging into his 30s should seek — a pitcher-friendly ballpark in the National League.

What wasn't there to like? Familiarity. Lester narrowed his final choice to two franchises with familiar faces: the Red Sox, his organization for 13 years before a July trade to Oakland this year; and the Cubs, who are run by Boston expats Theo Epstein, Jed Hoyer, Jason McLeod and recent hire Ryan Dempster, a longtime pitcher and a good friend of Lester's who one source said was a key player in Chicago's recruiting plan.

"There was a timer on this thing until there wasn't," said one source familiar with the negotiations, referring to an expected decision as soon as last Monday night. "The sense coming from that was that he's conflicted. It's a very tough choice for him."

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Late Tuesday night, Lester finally made the choice: He did pick the National League, but he picked the team that has posted five straight losing seasons and hasn't won the World Series since 1908. The Cubs bought Lester's services for $155 million over six years, but Lester is buying the biggest dream in sports — that the Cubs can be a world champion. It's not as far-fetched as you might think.

Lester turned down two safe picks in the Giants and Red Sox, ready-made contenders that have won six of the past 11 World Series titles. He also turned down the well-known pull of Boston. There he would have pitched for John Farrell, the Red Sox's current manager and former pitching coach under whom Lester had his most success. It's also the team for whom he won the 2007 World Series clincher one year after being diagnosed with cancer, when Red Sox owner John Henry would send his jet to fly him back and forth between Washington state and Boston for his chemo treatments.

Boston's bid came in about $20 million lower over six years. The Cubs will pay Lester more money per season ($25.8 million) than any free agent obtained on a multi-year deal. They handed a six-year contract to a pitcher who will be 31 next season, an unprecedented investment for a pitcher of that age. They essentially took the $140 million they offered Masahiro Tanaka last year (including the $20 million release fee from his Japanese club) and gave it — plus a $10 million sweetener — to a pitcher who is six years older. It may not be wise over the length of the deal, but Chicago needs only one championship out of it — and for the work ethic and influence of Lester, even as his stuff fades, to rub off on its young pitchers. There is a halo effect to the money, too.

It's not as hard to believe today as it was two months ago that the Cubs might be able to end their 106-year championship drought. New manager Joe Maddon may actually turn out to be the biggest free agent signing of this winter. A born leader, he has already energized Chicago's entire organization. And Lester, who can afford to chase a dream with two World Series rings already in his possession, will have the chance to become the first player in history to win a World Series with the Red Sox and Cubs.

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It wouldn't be a surprise to see free agent David Ross join on as Lester's personal catcher. Lester has a career 2.77 ERA in 29 games throwing to Ross, the lowest among the four catchers who have caught him at least a dozen times. With Lester joining fellow offseason additions Jason Hammel and Miguel Montero, as well as the best collection of young hitters in baseball, Chicago, which won only 73 games last year, could find another 15 wins to put itself into contention for a wild card. The Giants won the World Series last year after winning 88 games in the regular season. Chances are, the Cubs' young players will need a longer growth curve, but it wasn't crazy for Lester to believe the model can work sooner than later.

There is also the National League factor. All Lester needed to do was chat briefly with his good friend Jake Peavy for a few minutes about what it means for a starting pitcher in his 30s to get out of the American League and into the NL. Last year, at age 33, Peavy pitched to a 4.72 ERA and 1.43 WHIP in 20 starts for Boston. In 12 starts after his trade to the Giants, Peavy pitched to a 2.17 ERA and 1.04 WHIP. As Lester's stuff declines, the NL will be more forgiving.

Lester's contract covers his age 31-36 seasons. How much easier is the NL than the AL for starting pitchers at that age? Over the last 10 years, more than twice as many qualified pitchers age 31-36 posted an ERA+ of 120 or better in the NL (29) as did the same subset of pitchers in the AL (14).

So his choice came down to this: return to his original organization or take the challenge in Chicago. That he signed on to the dream more than a century in the making indicates just how much closer it is to becoming true.


On July 2, 2008, the Oakland Athletics forked over a record $4.25 million bonus to sign a 16-year-old kid from the Dominican Republic who threw in the mid-90s. Michael Ynoa, who turned down more money from Texas and Cincinnati, immediately became the fourth-highest paid player on the A's that year. GM Billy Beane said then that the 6-foot-7 righthander "has a chance to be a very special pitcher in the major leagues." Oakland pegged him as the best pitching prospect to come out of Latin America since Felix Hernandez six years earlier.

More than six years later, the A's gave up on Ynoa this week, packaging him with Jeff Samardzija in their trade with the White Sox. The 16-year-old would-be ace is now a 23-year-old set-up reliever – and still a project because he has thrown only 161 professional innings.

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What happened? Oakland signed him at the wrong time. A tall, thin 16-year-old kid who throws in the mid-90s is an injury waiting to happen. And Ynoa almost immediately broke down (needing Tommy John surgery in 2010), and it happened again (shoulder) and again (biceps).

When he was on the mound, Ynoa didn't command his fastball or breaking ball well enough and his changeup didn't improve much, so this year, the Athletics ended the idea that he could be a starting pitcher. He made 31 relief appearances in high A ball. Now the White Sox look at Ynoa and see a guy who can be a power reliever in the big leagues fairly quickly.

There are a couple of lessons here, one old and one new. The old one is the difficulty of projecting anything from a 16-year-old kid with high velocity. Baseball Prospectus ranked a 17-year-old Ynoa as the 20th-best prospect in baseball just seven months after he signed – five spots ahead of Andrew McCutchen.

The new lesson is becoming a familiar one: Velocity rules. When Oakland put Ynoa in the bullpen, his velocity jumped from the mid-90s to the upper-90s. He ditched the curveball and changeup for a power slider. And he began striking out hitters like never before: 12.6 per nine innings. Command? Well, that's still an issue, but the way the modern game embraces relief pitching — using more high-velocity arms for briefer outings — it's clear how the White Sox see a path for him to the big leagues.

The Athletics spent $4.2 million and six years developing Ynoa for another team, and it took the evolution of the game to open a way there. A major reason hitting is so hard in today's game is that there is a veritable assembly line of Michael Ynoas out there: young guys with power arms who lack command and touch but can find work throwing as hard as they can for one or two batters at a time. He may not be the next Felix Hernandez, but maybe he's the next Wade Davis, a pitcher who transforms himself from a failed starter into a shutdown reliever.