Cubs

Red Sox owner John Henry said team 'blew' Jon Lester negotiations in 2014

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USA TODAY

Red Sox owner John Henry said team 'blew' Jon Lester negotiations in 2014

As the saying goes, one person's loss is another person's gain. For the Cubs, this is especially true when it came to signing Jon Lester.

Lester entered spring training in 2014 on the last year of his contract with the Boston Red Sox. According to NBC Sports Boston's Justin Leger, the Red Sox reportedly offered Lester a four-year extension worth $70 million before the season started. 

As the story goes, the two sides did not agree to a new deal and the Red Sox traded Lester to the Oakland Athletics ahead of the 2014 trade deadline. Lester went on to sign a six-year, $155 million deal (with a vesting option for 2021) with the Cubs ahead of the 2015 season.

At a press conference on Monday, Red Sox owner John Henry admitted the team mishandled negotiations with Lester.

“I think we blew the Jon Lester — we blew the signing in spring training,” Henry said. “And for reasons that are pretty apparent now, which I won’t go into, but they’re apparent. But it wasn’t… you can see what’s gone on in free agency.

"The price of WAR has gone up radically that it’s difficult, whether it’s a pitcher or a position player, entering into a really long term contract with high dollars.”

The Red Sox are in a similar position now with former-White Sox starter Chris Sale, who will hit free agency after the 2019 season. Henry was asked if his philosophy has evolved regarding signing pitchers 30 years old or above.

“I think Chris [Sale] falls out of the norm because he’s just such a great — not just a great pitcher but a great part of the team as we saw in the World Series he had quite an impact just being on the bench during the World Series,” he said. “So he’s a special player.

“We would love to be able to sign him. I think he would like to as well. But there are the realities of the marketplace in budgets and this is his opportunity to be a free agent, so, potentially…something could happen.”

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Jon Lester's soccer career and other things to know about Cubs left-hander

Jon Lester's soccer career and other things to know about Cubs left-hander

Jon Lester is the best free agent addition in Cubs history, the guy who joined a last place club and helped push them to perennial contender status. He played a big part in the Cubs snapping their World Series drought, and even at 36 remains a durable, competitive starter.

Here’s a few things you may not know about the Cubs’ left-hander.

1. While playing in a soccer tournament in Italy at the age of 13, an Italian club approached Lester about playing professionally. He turned it down and the Red Sox drafted him five years later.

2. In August 2006, two months after making his MLB debut, Lester was diagnosed with a rare form of non-Hodgkin’s lymphoma. He underwent chemotherapy in the 2006-07 offseason and returned to the Red Sox in July 2007.

3. Lester’s charity, NVRQT, works to raise awareness and funds to fight pediatric cancer. Lester was the Cubs’ 2019 Robert Clemente Award nominee for his charitable efforts.

4. In 2011, Lester was featured on a wine label produced by Longball Cellars. Proceeds from “CabernAce” benefited the Fred Hutchinson Cancer Research Center in Seattle.

5. Lester, an avid golfer, once shot an 81 at Augusta National, according to Golf Digest.

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Anthony Rizzo has no regrets over signing bargain extension in 2013

Anthony Rizzo has no regrets over signing bargain extension in 2013

Back in 2013, the Cubs locked up a 23-year-old Anthony Rizzo on a seven-year, $41 million extension — with two options that could make it nine years for $74 million.

Rizzo is a cancer survivor, and gaining financial stability was a big thing for him. Seven years later, the deal is one of the best in baseball from a team perspective, but incredibly below market value overall.

However, the big first baseman, who’s emerged as a cornerstone for the Cubs, has no regrets over his decision.

“I’ve had the freedom from 22, 23 years old to financially do whatever I want and play freely,” Rizzo told NBC Sports Chicago’s Gordon Wittenmyer. “And I’m going to be able to do financially whatever I want for the rest of my life as long as I don’t make poor choices.

“At the end of this contract, it’ll make a lot of money, and I’m playing the game I love.”

The Cubs shut down extension talks with Rizzo over the winter, and he said it never got to the point of discussing any numbers. He has “no idea” what the Cubs’ thinking was on shutting down those talks, too.

The two sides will likely talk extension again in the future, but until then, the Cubs have Rizzo on an absolute bargain of a deal.

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