Extra Bases

Jon Lester Signs With Chicago Cubs in 6-Year, $155 Million Deal

John Tlumacki / Globe Staff

SAN DIEGO — He’s not coming back to Boston.

Former Red Sox lefthander Jon Lester made his long anticipated decision on which team to sign with late Tuesday night, and the choice is the Chicago Cubs.

The deal is reportedly for six years, $155 million. Cubs president of baseball operations Theo Epstein confirmed the Lester signing to the Globe's Nick Cafardo. The Red Sox fell significantly short with a six-year offer of $135 million according to the Globe.

The Lester deal contains an option for 2021 that could make the total package worth $170 million over seven years. If that option year becomes guaranteed, Lester’s average annual salary will be $25.8 million, making him the second-highest-paid pitcher behind the Los Angeles Dodgers’ Clayton Kershaw, who just completed the first season of a seven-year, $215 million deal that would put his average annual value at $30.7 million.

Lester — a three time All-Star who helped the Red Sox capture two World Series titles in 2007 and 2013 — was traded to the Oakland Athletics along with outfielder Jonny Gomes in July in exchange for slugging outfielder Yoenis Cespedes before becoming a free agent at the end of the season.

“This definitely propels us into Plan A, which is kind of neat. It’s a big day for us moving forward,” Cubs manager Joe Maddon said in the lobby of the Manchester Grand Hyatt in San Diego after the deal was announced. “It’s not often you get to win the lottery. We won the baseball lottery so far this year. It’s up to us now to put it in effect.

“It’s all theory right now. We’ve got to make it real. But you need pieces like this to make it real.”

Two weeks after getting dealt to the A's last summer, Lester stated that money was not going to be the primary factor in his decision.

"[The Red Sox] told me, ‘We’re going to be aggressive. You’re going to get blown out of the water by some of these [other] offers," Lester told the Boston Herald regarding his last conversation with Red Sox owner John Henry before leaving Boston. “I’m like, ‘I don’t need to be blown out of the water.’ Why would I need to be blown out of the water? That doesn’t make or break your decision, at least for me. I’m not going to the highest bidder. I’m going to the place that makes me and my family happy. If that’s Boston, it’s Boston."

Lester then insisted that comfort, not a record-setting contract, would be key in determining where he landed, but that didn't stop him from throwing some big numbers out there for the sake of argument.

"In the greater scheme of things, we’re talking about just a stupid amount of money," Lester said. "For me, I want to be comfortable. The way I look at it is, if someone gives you $170 million and someone gives you $150 million, is that $20 million really going to change your lifestyle? Same thing if the highest bidder is $100 million and the team you’re going to feel most comfortable with offers $80 million. Is that $20 million really going to make the difference in your lifestyle?...

"I want to be happy. I want my family to be happy. I want to be comfortable. If that means taking less money, it means taking less money. If it means going to the highest bidder, it means going to the highest bidder, but that’s not going to dictate where I’ll be happy."

At the Boston baseball writer's dinner in January, Lester contradicted himself a bit when he told the assembled media that he "doesn't want to be the guy to set the market back" while also saying he wanted to stay in Boston and admitted he would have to take a hometown discount to do so.

Lester is now headed to a team that hasn’t made the playoffs since 2008, but he knows both Epstein and general manager Jed Hoyer from their time together in Boston.

Maddon also spoke to the media Tuesday afternoon prior to the announcement and said he spoke to Lester for the first time before Thanksgiving. He said those talks centered around hunting and fishing, and he was pleased that that was something Lester liked to do now that he has bench coach Dave Martinez on his staff. Martinez is an avid outdoorsman.

"As part of the Rays, our guys liked to hunt and fish a lot, and liked to shoot things," Maddon said. "We would set things up on different road trips. Like a couple of years ago, Wade Davis shot a black bear in Toronto prior to the playoffs. I thought that was outstanding. That gave me even more confidence putting him in a game, like in the seventh or eighth inning, facing a normal righthanded hitter. He shot a black bear, 300-pound black bear. I like when the guys do things like that. [Lester] relayed to me the fact that he likes to hunt and fish. I assured him that I don't, but I respect it.

"Otherwise we just talked about previous games and series, and how this unfolded over the last couple of years, and how much respect I had for him."

Maddon had been used to small payrolls in Tampa Bay.

"I've not been on this side since my days with the Angels, when I got an email in Italy that we had signed Vladimir Guerrero," said Maddon, who was a coach in Anaheim before switching to Tampa Bay. "I think that definitely sends that message how Theo and the group feel about this particular group. But understand, we have a lot of young players that have to grow up as quickly as possible. But having Jon there adds to the flavor and the possibility."

The Cubs management is making over the team in a big way.

Chicago has a pending $20 million, two-year deal with righthander Jason Hammel, traded by the Cubs to the Athletics last summer. Earlier Tuesday, the Cubs acquired All-Star catcher Miguel Montero from Arizona for minor league righthanders Jeferson Mejia and Zack Godley — a deal that added $40 million in payroll over the next three years.

Chicago’s rotation is likely to also include Jake Arrieta, Travis Wood, and Kyle Hendricks.

Lester went 110-63 with a 3.64 ERA with more than 1,500 innings pitched for the Red Sox. After being dealt to Oakland, Lester went 6-4 with a 2.35 ERA. Overall, Lester finished the 2014 season with a career-best 2.46 ERA to go along with a 16-11 record.

The former Red Sox ace has been particularly dominant in his World Series appearances, putting up a 3-0 record with a 0.43 ERA in three starts. Overall in the postseason, Lester checks in with a 6-4 mark and 2.57 ERA in 14 playoff starts.

The 30-year-old southpaw was not able to reach a contract extension with the Red Sox this past spring, turning down a four-year, $70 million offer. He earned $13 million last season in the final year of his contract.

The Cubs, Giants, Dodgers — along with the Red Sox — had been mentioned as the finalists in contention to sign Lester to a long-term deal which was expected to exceed the $150 million range over six years.

On Monday, Red Sox GM Ben Cherington said regardless of the Lester outcome, the plan is to build a competitive rotation for 2015 one way or another.

“We’ve never looked at it like Plan A, B, C, we’ve looked at it like we need to build a rotation so we have to be in on all sorts of stuff and we have been in on all sorts of stuff all offseason," Cherington said. "To this point in the offseason, there’s probably — between free agent possibilities and trade possibilities — 15-20 starting pitching scenarios we’ve talked about and worked on and so obviously not all those are going to land and more of those won’t land than will land, so we just have to stay involved and keep working.”

Cherington said the bottom line is that Red Sox fans are most concerned with rooting for a winning team.

"I think our fans expect us to deliver on the field and win games," he said. "In order for us to give the best chance, we have to add to the pitching staff. There are all sorts of ways to do that. Of course there’s a connection to certain players more than others. But ultimately they care about the people we put on the field."

Cherington on Tuesday confirmed a Globe report that the team has spoken with former Sox pitcher Justin Masterson, who came up through the Boston farm system before being traded in 2009 during his second big league season. The soft-tossing righthander went 7-9 with a 5.88 ERA for Cleveland and St. Louis this year, when he spent time on the disabled list because of a knee injury. The Globe's Nick Cafardo reported that the Red Sox offered Masterson a one-year deal.

Stay with for upcoming reaction and analysis on the Lester signing Wednesday.

Information from The Associated Press was used in this story.

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