Jon Lester still getting settled in Chicago

The Cubs’ new ace, Jon Lester, didn’t make it out of the fifth inning Sunday night against the Cardinals.
The Cubs’ new ace, Jon Lester, didn’t make it out of the fifth inning Sunday night against the Cardinals.(Jonathan Daniel/Getty Images)

CHICAGO — In a dingy Wrigley Field tunnel leading from the home clubhouse to the dugout, Cubs manager Joe Maddon walked by Jon Lester, patted him on the side, took a left, stopped, turned around, and said he had gone the wrong way. “I’ve done that four times already,” replied Lester.

Maddon and Lester are just a couple of American League East expats taking up residence at Wrigley, counted on to accelerate the Cubs’ grand overhaul and eventually end a bordering-on-biblical World Series drought (107 years and counting). It’s all new for Lester — new league, new team, new manager, new city.


Even though his Red Sox tenure ended July 31, when he was shipped to Oakland, it’s still a bit jarring to see Lester — who said they would have to rip the Red Sox jersey off his back — having his new jersey prominently displayed in the Cubs Store on North Clark Street.

The erstwhile Sox ace is clearly still trying to settle in and get comfortable in his new baseball home, even if it has a familiar look with Cubs president of baseball operations Theo Epstein, general manager Jed Hoyer, and a historic ballpark.

Lester doesn’t bear any ill will toward the Red Sox. He’s not holding a grudge that they were $20 million below Chicago’s winning bid (six years, $155 million) this winter. He is not fuming because they offered Rick Porcello more money before he had even thrown a meaningful pitch for the Sox than they offered him last spring.

“I understand. I told [Red Sox owner] John [Henry] that night he came back to the house, I will always appreciate everything they did for me and my family in particular times in my career,” said Lester. “By no means is there any hard feelings toward those guys. It is what it is. They’re trying to run their business. I’m trying to run mine. At the end of the day, you have to make an informed decision, and I feel like we did that.


“We’re happy with where we’re at. There is always going to be the second-guessers and all that. We’re happy. We’re ready to start this new chapter.”

That new chapter got off to a bit of a rough start on Sunday night. Lester lasted just 4⅓ innings in the Cubs’ opener, allowing eight hits and three runs in a 3-0 loss to the archrival St. Louis Cardinals.

While Cubs fans had to hold their bladders due to a paucity of restrooms caused by the ongoing renovations at Wrigley, Lester struggled to hold runners on. The Cardinals stole three bases off him, including a double steal.

It’s no secret Lester has been awkward and uncomfortable throwing to bases for awhile. He didn’t attempt a pickoff throw to first base all of last season. The Cubs have changed his pickoff motion.

With the cancellation of Tuesday’s Cubs game creating a two-day layoff, Lester’s throwing became a hot topic for the local media.

Both Lester and Maddon said the issue was overblown. Lester was asked directly on Wednesday if he had the “yips,” which is truly a four-letter word for baseball players.

Bet Lester never thought he would miss the Boston media.

Playing for Oakland last year showed Lester what it’s like working outside of Boston. But it was still a tough decision for him when the Sox re-engaged in free agency, making two visits to his Atlanta home.


Lester said his heart longed for the Hub after spending 13 seasons in the Red Sox organization, nine at the big league level.

He said he “never felt unwanted” by the Sox or that their interest was a public relations ploy.

Lester said that, contrary to belief, the $70 million offer the Sox made last spring didn’t signal the end of his Red Sox career. “By no means was it the end-all, be-all right there,” he said. “The conversation continued. I know it’s hard for people to believe.”

Lester said he was aware of the four-year, $82.5 million extension the Sox gave to Porcello, who is just 26. The extension kicks in next year.

“I’m happy for Rick. That’s a good thing,” said Lester. “I read some of the stuff that he said about Boston. It’s all true, about [coach Brian Butterfield] and the expectations and all that stuff. He said all the right things. Obviously, in signing that deal he believes in all those things. That’s awesome for him and awesome for the Red Sox that they got a guy that is going to be relied upon.”

Part of the Sox’ thinking for not extending more for Lester was that at age 31 he was — by baseball standards — too old to produce at the same level for the next six seasons. That he could be one of those overpaid, over-30 players that Henry, who also owns the Globe, told Bloomberg Businessweek last April represent a market inefficiency in MLB.


The reliable lefty’s greatest strength — his workload — was held against him. Suddenly, durability morphed into wear and tear.

Epstein acknowledged that there is risk in dipping into the free agent pitching market. But after three years of rebuilding the organization and given his familiarity with Lester, it was a risk worth taking.

Everything about the Cubs, including the roster, is under construction, as the Friendly Confines get a four-phase, $575 million facelift. Wrigley’s footprint is one giant construction site. Like Epstein’s Cubs, the remodel job is laid bare for all to see.

The famed Wrigley bleachers are currently closed, and the back side of the new videoboard is still exposed.

The ballpark and the team are metaphors for each other, works in progress.

One Cubs fan brought a sign to Wednesday’s 2-0 win over St. Louis that read, “Cubs: Under Construction since 1909.”

“You’re coming to an organization that hasn’t been expected to win the last couple of years,” said Lester. “Being with the Red Sox, you’re expected to win every year, so there is no rebuilding, there is no prospect years, there is none of that. It’s exciting to be here. It’s exciting to be kind of the light at the end of the tunnel for these fans.

“There is a very similar outlook on baseball [to Boston], you know, smart, and they’re passionate about the Cubs. I’m just excited to be a part of this.”


Former Sox catcher David Ross, now with the Cubs, said he has seen Lester take on more of a leadership role than in Boston.

“Which has been really cool for me to see and a maturity factor,” said Ross. “He has got a different role over here as far as he is the big man on the team.”

Lester said he will “always cherish” his memories of Boston. He is still in touch with former teammates such as Mike Napoli, Shane Victorino, David Ortiz, and Dustin Pedroia.

“Me and Pedey grew up together, basically, so I still keep in contact with him quite a bit about things,” said Lester. “David is David. He has always been a mentor to me.”

Lester even waded into the debate about whether the Red Sox have an ace in his absence or if the title is in abeyance.

“I’ve always been a big believer in there is no ace,” he said. “Your ace is that day’s pitcher. We’re all big leaguers. We’re all really good at our job . . . The ace label and all that stuff is for you guys.”

Take that, nonbelievers in the Sox’ pitching plan.

Lester seemed happy to answer questions about Boston in the bowels of Wrigley because in a time of transition, he was back in familiar territory.

Right now, the Lester family’s abode, not too far from Wrigley, is littered with boxes.

“As soon as those are gone, it will start feeling more like home,” Lester said. “It’s going to take some time. It’s going to take time to get comfortable, get to know everything and really kind of settle in here.”

Lester was talking about his personal dwelling, but it became clear he was talking about his new address too.

His career has taken a new turn. There is no stopping and going back now.