Why Cubs bet big on Jon Lester (and won’t look back)


Why Cubs bet big on Jon Lester (and won’t look back)

Why have you been so durable throughout your career?

Jon Lester listened to that question after the Cubs revealed their $155 million lefty had been dealing with a “dead arm” in spring training. He shrugged his shoulders and paused for a few seconds, searching for an answer he couldn’t find.

“I don’t know,” Lester said at least four times. “Luck?”

Lester is obviously better than what he’s shown Cubs fans in April (0-2, 6.23 ERA), and he will get a chance to prove that on Friday afternoon at Wrigley Field against the Milwaukee Brewers.

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The bigger issue is how a 31-year-old pitcher holds up across the next six seasons. The Cubs went into this with their eyes wide open, betting Lester would age gracefully and become their version of Andy Pettitte.

Remember how the Cubs planned an entire offseason around waiting for Masahiro Tanaka, only to have the New York Yankees blow them away with a $175 million investment?

Well, the Yankees put Tanaka on the disabled list this week with a strained right forearm and tendinitis in his right wrist – after shutting him down last season with a partially torn ulnar collateral ligament in his right elbow, the kind of injury that usually signals Tommy John surgery. 

Texas Rangers ace Yu Darvish – another Japanese pitcher the Cubs once bid on – is already recovering from his Tommy John surgery. The Philadelphia Phillies don’t know if Cliff Lee’s left elbow will allow the Cy Young Award winner to throw another pitch again. One season into a six-year, $105 million contract, the Cincinnati Reds aren’t sure if Homer Bailey will need the Tommy John procedure.

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If Theo Epstein isn’t numb to that kind of news by now, the Cubs president of baseball operations certainly understands the odds and realizes no one is immune to the epidemic.

“You know it going in,” Epstein said. “That’s why we just kind of curse ourselves up and down for even considering big money on free-agent pitchers at the beginning of every offseason. Because you know the injury risk and you don’t want to do it. But at some point you kind of have to.

“If you don’t want to bet on first-round pitchers, because the position players are a safe bet, and you don’t want to bet on young pitchers as the headliners in trades because you can get guys like Addison Russell back, then you can’t sit there and hold your nose on free-agent pitching and say no.

“You’ll end up with no pitching. You have to do it one way or the other. I will say this: The worst part of the job is the fear of the phone ringing and it being a trainer with franchise-altering news about one of your pitchers. That (bleeping) sucks living with that every day. But it’s part of the game. It’s the same for everybody.”    

The Cubs bet on Lester because they understood his personality, medical history, work ethic and family values through all their Boston Red Sox connections. It’s hard to argue with the track record: 30-plus starts in each of the last seven seasons, and at least 200 innings every year except for 2011, when he threw 191.2.  

“The kid answers the bell every five days,” Cleveland Indians manager Terry Francona said. “He keeps himself in phenomenal shape. Loves to pitch. It’s scary, I think, for teams to give away that kind of money. But…I’d have a hard time finding somebody you would (rather) give it to. He’s phenomenal in just about every aspect of everything he does.”

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Francona grew close to Lester while managing the Red Sox amid all the drama at Fenway Park. Lester got the cancer diagnosis during the 2006 season, beat anaplastic large cell lymphoma and then won the clinching game of the 2007 World Series against the Colorado Rockies at Coors Field.

The Cubs got Russell in the Fourth of July deal for Jeff Samardzija, who immediately noticed Lester’s consistency when the rental pitcher joined the Oakland A’s after a deadline trade from Boston.

“The dude’s a horse,” said Samardzija, now pitching for the White Sox in his walk year and expecting to sign his own nine-figure contract. “You look in this league, there are 30, 40 horses out there that you write a check for.

“You just close your eyes, because you know that no matter what amount you pay ‘em, they’re going to go do their job and it’s going to be a good investment. If I was an owner, the No. 1 thing that I would want is wherever I spend my money, when it’s all said and done, I was happy who I gave it to and how it was spent.

“I think they’re going to be very happy with what they get out of Jonny. He’s not going to shut it down. He’s not going to be content. And I think that’s what it’s all about, being that same guy you were when you were a rookie.”

Lester is obsessive with his routine, trying to throw the exact same bullpen sessions and warm-up pitches, whether it’s preparing for a minor-league scrimmage or the World Series.

Otherwise, Lester thinks, the emotions would get out of control. That tunnel vision has probably helped him stay healthy, though it doesn’t completely explain or guarantee his durability.     

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“We all have things that we deal with through the season that come up,” Lester said. “I’ve been fortunate enough to kind of, I guess, minimize those things to where I’m still able to pitch.

“If I had an answer, I could give it to guys that struggle with being healthy. But I don’t (have an answer). I just try to (go for) as many starts as I can. That’s all I try to worry about.” 

It hasn’t been the first impression the Cubs wanted, but the last word will belong to Lester, who has a career 2.57 ERA in 84 postseason innings and those two World Series rings from the Red Sox.

“Some guys start fast and finish terrible,” Lester said. “Other guys start slow and finish good. So I’d rather be the latter. That’s what you play for – the end of the year.” 

Changes aren't exactly popular, but Cubs and Sox — except maybe Willson Contreras — will adapt to baseball's new pace-of-play rules

Changes aren't exactly popular, but Cubs and Sox — except maybe Willson Contreras — will adapt to baseball's new pace-of-play rules

MESA, Ariz. — We know Willson Contreras doesn’t like baseball’s new pace-of-play rules.

He isn’t the only one.

“I think it’s a terrible idea. I think it’s all terrible,” Jon Lester said last week at spring training, before the specifics of the new rules were even announced. “The beautiful thing about our sport is there’s no time.”

Big surprise coming from the Cubs’ resident old-schooler.

The new rules limit teams to six mound visits per every nine-inning game, with exceptions for pitching changes, between batters, injuries and after the announcement of a pinch hitter. Teams get an extra mound visit for every extra inning in extra-inning games. Also, commercial breaks between innings have been cut by 20 seconds.

That’s it. But it’s caused a bit of an uproar.

Contreras made headlines Tuesday when he told reporters that he’ll willingly break those rules if he needs to in order to put his team in a better position to win.

“I’ve been reading a lot about this rule, and I don’t really care. If I have to pay the price for my team, I will,” Contreras said. “There’s six mound visits, but what if you have a tight game? … You have to go out there. They cannot say anything about that. It’s my team, and we just care about winning. And if they’re going to fine me about the No. 7 mound visit, I’ll pay the price.”

Talking about pace-of-play rule changes last week, Cubs manager Joe Maddon said his team would adapt to any new rules. In Chicago baseball’s other Arizona camp, a similar tune of adaptation was being sung.

“Obviously as players we’ve got to make adjustments to whatever rules they want to implement,” White Sox pitcher James Shields said. “This is a game of adjustments, we’re going to have to make adjustments as we go. We’re going to have to figure out logistics of the thing, and I would imagine in spring training we’re going to be talking about it more and more as we go so we don’t mess it up.”

There was general consensus that mound visits are a valuable thing. So what happens if a pitcher and catcher need to communicate but are forced to do it from 60 feet, six inches away?

“Sign language,” White Sox catching prospect Zack Collins joked. “I guess you have to just get on the same page in the dugout and hope that nothing goes wrong if you’re out of visits.”

In the end, here’s the question that needs answering: Are baseball games really too long?

On one hand, as Lester argued, you know what you’re signing up for when you watch a baseball game, be it in the stands at a ballpark or on TV. No one should be shocked when a game rolls on for more than three hours.

But shock and fans' levels of commitment or just pure apathy are two different things. And sometimes it’s a tough ask for fans to dedicate four hours of their day 162 times a year. So there’s a very good reason baseball is trying to make the game go faster, to keep people from leaving the stands or flipping the TV to another channel.

Unsurprisingly, Lester would rather keep things the way they are.

“To be honest with you, the fans know what they’re getting themselves into when they go to a game,” Lester said. “It’s going to be a three-hour game. You may have a game that’s two hours, two hours and 15 minutes. Great, awesome. You may have a game that’s four hours. That’s the beautiful part of it.

“I get the mound visit thing. But what people that aren’t in the game don’t understand is that there’s so much technology in the game, there’s so many cameras on the field, that every stadium now has a camera on the catcher’s crotch. So they know signs before you even get there. Now we’ve got Apple Watches, now we’ve got people being accused of sitting in a tunnel (stealing signs). So there’s reasons behind the mound visit. He’s not just coming out there asking what time I’m going to dinner or, ‘Hey, how you feeling?’ There’s reasons behind everything, and I think if you take those away, it takes away the beauty of the baseball game.

“Every game has a flow, and I feel like that’s what makes it special. If you want to go to a timed event, go to a timed event. I’m sorry I’m old-school about it, but baseball’s been played the same way for a long time. And now we’re trying to add time to it. We’re missing something somewhere.”

Whether limiting the number of mound visits creates a significant dent in this problem remains to be seen. But excuse the players if they’re skeptical.

“We’ve got instant replay, we’ve got all kinds of different stuff going on. I don’t think (limiting) the mound visits are going to be the key factor to speeding this game up,” Shields said. “Some pitchers take too long, and some hitters take too long. It’s combination of a bunch of stuff.

“I know they’re trying to speed the game up a little bit. I think overall, the game’s going as fast as it possibly could. You’ve got commercials and things like that. TV has a lot to do with it. There’s a bunch of different combinations of things. But as a player, we’ve got to make an adjustment.”

Albert Almora's strong connection to Team USA baseball

Albert Almora's strong connection to Team USA baseball

Who was Theo Epstein’s first draft pick with the Cubs?

The answer to that trivia question will always and forever be Albert Almora Jr. picked sixth overall in the 2012 amateur draft.

In some ways, the young outfielder from Florida became the forgotten man in the stable of can’t-miss prospects that Epstein and top lieutenants Jed Hoyer and Jason MacLeod amassed since their arrival over six years ago. While players such as Kris Bryant, Kyle Schwarber and Ian Happ zoomed through the minor leagues on their way to the majors, Almora took a different path – one that included seven different stops over parts of five developmental seasons before he broke into the big leagues during the 2016 season.

But Almora’s road to the majors began years before he was selected by the Cubs, when he began playing for Team USA as a 13-year-old. Over the next several years, Almora played for the Red, White & Blue seven times, his final appearance coming in 2015. The seven appearances are the most in the history of USA Baseball, and Almora recognizes the impact his time with the national squad had on his playing career.

“[It was] one of the best experiences of my life," he said. "Every year I had something special to play with, unbelievable guys, went to crazy places, and out of those six years, five of them came with a gold medal so that was pretty special as well. Also, that helped me in my baseball life, how to experience things and learn from those type of experiences.

“I’m a Cubbie and that’s what’s on my chest right now, but Team USA will always have a special place in my heart.”

While Almora carries those national team experiences with him every day, his main focus coming into the 2018 season is becoming a consistent difference-maker. Almora made only 65 starts during the 2017 campaign, and 63 percent of his at-bats last year came against left-handed pitching, against which he hit a robust .342. That led to a platoon role in a crowded outfield, with Jason Heyward, Kyle Schwarber, Jon Jay, Ian Happ and Ben Zobrist all taking turns on the merry-go-round. But with the departure of Jay, Almora believes his time is near.

“I have the most confidence in myself that I can play every day, but I try not to think about that kind of stuff because it’s out of my control," Almora said. "All I control is like last year what I did; whenever I was given an opportunity, I tried to do my best and help the team win.”

Almora’s ultimate role on the 2018 Cubs remains to be seen, but there’s no question that Theo’s first Cubs pick will earn whatever role he ends up with, and the foundation of Almora’s journey to Clark and Addison was laid many summers ago during his time with Team USA.