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The top 10 Cubs stories of the 2010s, #4: The signings of Joe Maddon and Jon Lester

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With these signings, the Cubs went into win-now mode.

Photo by Harry How/Getty Images

The Cubs finished the 2014 season with a 73-89 record. That was a seven-game improvement over 2013, but it still didn’t portend instant contention, even with the arrival of prospects Javier Baez, Jorge Soler and Kyle Hendricks late in that season.

Rick Renteria had been hired as manager before the 2014 season and given a three-year contract with club options for 2017 and 2018.

(Can you imagine that now? Renteria managing the Cubs for five seasons?)

And then, in October 2014, Joe Maddon was simply dropped in the Cubs’ laps. When Tampa Bay Rays executive Andrew Friedman left that ballclub to run the Dodgers front office, that triggered an opt-out in Maddon’s contract, which he exercised.

Shortly after that, Renteria was fired and Maddon was hired by the Cubs. Joe was given a five-year deal. Here’s what Josh wrote here at the time:

From the moment Maddon’s resignation was announced, there was speculation that he would manage the Cubs, despite the fact that the Cubs already had a manager. Reports leaked out on Wednesday that the Cubs had come to an agreement with Maddon, although those reports were quickly denied. However, no one denied that the Cubs were interested in hiring Maddon and Maddon, in the past, had made clear his admiration for the Cubs, Wrigley Field and the history and tradition of the team. Cubs president Theo Epstein had also shown his admiration for Maddon in the past, interviewing him for the Red Sox job after the 2003 season where he was the second-choice behind Terry Francona.

This is rather long, but I thought it was worth posting here again the entire statement Theo Epstein issued after Renteria was let go:

Today we made the difficult decision to replace Rick Renteria as manager of the Chicago Cubs. On behalf of Tom Ricketts and Jed Hoyer, I thank Rick for his dedication and commitment, and for making the Cubs a better organization.

Rick’s sterling reputation should only be enhanced by his season as Cubs manager. We challenged Rick to create an environment in which our young players could develop and thrive at the big league level, and he succeeded. Working with the youngest team in the league and an imperfect roster, Rick had the club playing hard and improving throughout the season. His passion, character, optimism and work ethic showed up every single day.

Rick deserved to come back for another season as Cubs manager, and we said as much when we announced that he would be returning in 2015. We met with Rick two weeks ago for a long end-of-season evaluation and discussed plans for next season. We praised Rick to the media and to our season ticket holders. These actions were made in good faith.

Last Thursday, we learned that Joe Maddon – who may be as well suited as anyone in the industry to manage the challenges that lie ahead of us – had become a free agent. We confirmed the news with Major League Baseball, and it became public knowledge the next day. We saw it as a unique opportunity and faced a clear dilemma: be loyal to Rick or be loyal to the organization. In this business of trying to win a world championship for the first time in 107 years, the organization has priority over any one individual. We decided to pursue Joe.

While there was no clear playbook for how to handle this type of situation, we knew we had to be transparent with Rick before engaging with Joe. Jed flew to San Diego last Friday and told Rick in person of our intention to talk to Joe about the managerial job. Subsequently, Jed and I provided updates to Rick via telephone and today informed him that we will indeed make a change.

We offered Rick a choice of other positions with the Cubs, but he is of course free to leave the organization and pursue opportunities elsewhere. Armed with the experience of a successful season and all the qualities that made him our choice a year ago, Rick will no doubt make an excellent major league manager when given his next chance.

Rick often said he was the beneficiary of the hard work of others who came before him. Now, in the young players he helped, we reap the benefits of his hard work as we move forward. He deserved better and we wish him nothing but the best.

We have clung to two important ideals during our three years in Chicago. The first is to always be loyal to our mission of building the Cubs into a championship organization that can sustain success. The second is to be transparent with our fans. As painful as the last week was at times, we believe we stayed true to these two ideals in handling a sensitive situation. To our fans: we hope you understand, and we appreciate your continued support of the Cubs.

The bottom line was that Theo & Co. thought this was a unique opportunity to add a successful manager with a very different viewpoint to the ballclub. I believe any baseball front office confronted with a similar choice would have made the same decision. Obviously, it succeeded beyond any of our dreams. This Sun-Times article, an excerpt from David Kaplan’s book “The Plan,” describes how Theo & Jed sat with Maddon in front of his RV on a beach near Pensacola, Florida, to complete the signing. It’s a story you couldn’t have made up.

Here are about five minutes of highlights [VIDEO] from Maddon’s introductory news conference on November 3, 2014.

It was at that moment that I knew, and I think every Cubs fan knew, that this new manager wasn’t going to be like any who had preceded him. For lack of a better term, he “got it,” he understood what was going to be needed to bring the Cubs the championship that had eluded them for more than a century. This, even though Maddon had not grown up or ever lived in Chicago and had no previous connections to the city or Cubs organization.

The Cubs were immediately thrust into the realm of contention, and were installed as favorites to sign that offseason’s top free agent, Jon Lester.

You know, I don’t think Lester would have signed with the Cubs had Maddon not been hired. It was that hire that sent the message to Lester (and others) that the Cubs were serious about contending in 2015. Beyond that, Buster Posey actually went to Lester’s offseason home in Georgia and tried to sell Jon on joining the Giants:

When Lester answered the door, at the head of the group was Buster Posey, the Giants’ franchise catcher, who had driven three hours from his home.

“Buster put his hand out and said, ‘Hi, Jon, I want to be your catcher for the next six years,’” said Larry Baer, the Giants’ chief executive, who was among the team’s contingent along with Manager Bruce Bochy and Brian Sabean, the head of baseball operations.

The Giants offered more guaranteed money than the Cubs did, but Lester’s previous relationship with Theo Epstein from their time together in Boston, along with Maddon’s presence, clinched the deal for the Cubs.

Lester got off to a rough start in Chicago, posting a 6.23 ERA in April 2015, but in 28 starts from May 1 through the end of the 2015 season had a 2.99 ERA and 1.069 WHIP, presaging his second-place Cy Young season in 2016. Lester’s probably the best free-agent signing in Cubs history and maybe the best of anyone in Chicago sports history.

And without those two men, the Cubs probably don’t win the 2016 World Series.