How Oakland helped redirect Jon Lester and turn Cubs into contenders


Maybe institutional arrogance would have inevitably driven Jon Lester out of Fenway Park. The Boston Red Sox lowballed their homegrown ace – really their only consistently reliable drafted-and-developed starting pitcher in a generation – with a no-chance spring-training extension offer in 2014.

But Oakland A’s baseball czar Billy Beane gave the Cubs another assist at that trade deadline – four weeks after the Jeff Samardzija/Addison Russell deal – by shipping out Yoenis Cespedes and acquiring Lester in a move that shocked the industry.

That meant Lester – a creature of habit comfortable in Boston – would get an eye-opening experience outside Red Sox Nation and broaden his horizons a little bit. The Red Sox couldn’t seriously play the loyalty card anymore, while the A’s couldn’t tag Lester with a qualifying offer after his no-decision in an American League wild-card loss to the Kansas City Royals.

The Oakland Coliseum doesn’t have a reputation for being family-friendly, and the Cubs played up all the planned amenities at a renovated Wrigley Field during Lester’s recruiting visit to Chicago, paving the way to a six-year, $155 million megadeal with a last-place team that needed to show the franchise would be serious about winning.

The butterfly effect is a fascinating concept while looking back on how Theo Epstein’s baseball-operations group built the team with the best record in baseball. Seeing Lester (11-4, 2.95 ERA) pitch against a green-and-gold backdrop on Friday night on the same lot where the Golden State Warriors built a Super Team will be another reminder.

[MORE: John Lackey came to Chicago to win a World Series]

“It was a big surprise,” Lester said. “I didn’t actually think I would get traded. I knew that was a possibility. But I was just thinking if things didn’t work out, they would want that draft pick, knowing those guys (in Boston). It ended up working out.”

Lester will always remember July 31, because it’s his oldest son’s birthday. Hudson turned four the day Lester got traded from the organization that drafted him out of high school in 2002 and gave him two World Series rings.  

“We were having a party,” Lester said, at the family’s house in suburban Boston. “I had found out that morning. I went and got some stuff from the (clubhouse). We all sat around and we were watching MLB (Network). Somebody would get up and take a phone call and we’d be like: ‘Oh, OK.’

“And then Andrew Miller would come (back) in and (say): ‘Yeah, I’m going to Baltimore.’ It would come up on the screen: ‘Andrew Miller traded to Baltimore.’ And then Stephen Drew got traded to the Yankees, who we were playing at the time. ‘Lack’ (John Lackey) got traded (to St. Louis).

“We were all sitting around just watching MLB (Network) while the kids were going crazy. And paused for some cake and went back to watching MLB.

“It was just a really weird day that will definitely go down as a lasting memory for my family.”

[SHOP: Gear up, Cubs fans!]

The Cubs focused most of their energy on upgrading the bullpen before this week’s non-waiver deadline, getting game-over closer Aroldis Chapman and a few more complementary pieces. While supply-and-demand dynamics, long-range planning and intradivision/crosstown politics factored into those decisions, the bottom line is the Cubs already made their biggest moves.

“We’re all kids here in the toy aisle,” Lester said. “We’re all trying to play GM and say: ‘Why don’t you get this guy?’ There’s always logistics that we don’t understand, (things) that we don’t see. ‘Just get this guy and give him $10 million bucks next year’ – we don’t understand the ramifications of that.

“It’s still fun to sit back and say: ‘What if? What if we get this guy? What it we get that guy?’ You’re definitely paying attention to it. (But) I pay less attention to it now that I don’t have to worry about it.”

Epstein’s front office ignored the rule already broken for Lester and gave no-trade protection – and $240 million combined – to Ben Zobrist and Jason Heyward with October power pitching in mind. How much is enough? A lineup anchored by MVP candidates Anthony Rizzo and Kris Bryant – with All-Star leadoff guy Dexter Fowler at the top – is either good enough or it’s not.

Jake Arrieta must perform at a Cy Young Award winner-level in the playoffs. Lackey will show up for the Big Boy Games or he won’t. And the Cubs aren’t going very far in October without Lester living up to his reputation as one of the best big-game pitchers of his generation.

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