Jon Lester: The First Big Step in the Cubs’ Revival

Sep 30, 2014; Kansas City, MO, USA; Oakland Athletics starting pitcher Jon Lester (31) throws a pitch against the Kansas City Royals during the first inning of the 2014 American League Wild Card playoff baseball game at Kauffman Stadium. Mandatory Credit: Denny Medley-USA TODAY Sports
Sep 30, 2014; Kansas City, MO, USA; Oakland Athletics starting pitcher Jon Lester (31) throws a pitch against the Kansas City Royals during the first inning of the 2014 American League Wild Card playoff baseball game at Kauffman Stadium. Mandatory Credit: Denny Medley-USA TODAY Sports

Ace southpaw Jon Lester agreed to a six-year, $155 million deal with the Chicago Cubs early Wednesday morning, signaling the first big step in the Cubs’ revival.

It’s been a long time since the Chicago Cubs have been relevant in any way.  However, under general manager Theo Epstein, everyone around baseball knew that this would be a tough, but doable rebuilding.  And when rebuilding, why not bring in some familiar parts that worked before?

The Cubs and lefty Jon Lester, the top free agent starting pitcher in the market this year, agreed on a six-year, $155 million deal that’ll send him to Wrigley, reunite him with his old boss in Epstein and put the Cubs a solid starter away from contention in the NL Central.

Along with Epstein, Lester is reunited with Jed Hoyer and Jason McLeod, two other Cubs executives, along with Epstein who all worked for Boston, who Lester developed a close relationship with during his battle with cancer early in his career.

Now, don’t get mistaken, the Cubs aren’t winning anything in 2015 except maybe their first winning record since 2009 (83-78) unless they make an improbable Wild Card run, which would mark their first playoff appearance of any kind since they were swept in three games in the 2008 NLDS.

“It’s not often you get to win the lottery,” new Cubs manager Joe Maddon said.  “And we won the baseball lottery so far this year; but now it’s up to us to put it into effect.  It’s all theory right now.  We’ve got to make it real.  But you need piece like this to make it real.”

“Whoever got Jon Lester is a lucky team,” Cubs special assistant Ryan Dempster said.  “It’s great for the city of Chicago.  He’s a stud.”

Lester, is a good piece to “make it real.”

Lester went 16-11 between Boston and Oakland last year with a career-best 2.46 ERA with 220 strikeouts in 219 innings.  Given his improved ERA throughout the last three seasons and his career playoff record, there’s no doubt that Lester brings a lot more to the mound at Wrigley Field than anyone has in a very, very long time.

However, it was originally thought that Lester would go back to Boston since “he was a Red Sock through and through.”

In fact, it was more Boston screwing things up with Lester that helped push him toward the Windy City.

Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the first inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports
Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the first inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports

The Red Sox originally lowballed Lester with a four-year, $70 million deal last March, then tried to take advantage of a $20 million hometown discount, offering him a six-year, $135 million deal, which was obviously rejected. He refused to discuss a new deal with Boston several times, including at the All-Star break, forcing the Sox to trade him to Oakland in exchange for outfielder Yoenis Cespedes.  Lester claimed that he had no hard feelings toward Boston and didn’t originally rule out a return.  That was, until the Red Sox’ number didn’t even come close to Chicago, or San Francisco for that matter. The Giants, another team in the market for Lester, was rumored to be willing to give Lester no more than a six-year, $150 million deal.  Somehow Chicago spent the extra $5 million which pushed Lester to enter a new frontier.

Maddon and Lester are going to be two of the main people responsible to push the Cubs to their first World Series since 1908.  Maddon always admired Lester from a distance from their Boston-Tampa Bay rivalry days.

“I always admired his work from a distance,” Maddon said.  “This is a guy when the game is really big he was always at his best.”

In Lester’s case for 2015, every game will be really big.  Considering Lester’s background and his dominance pitching in the American League, let alone an AL East division in its prime, the National League could be good for the southpaw.  There’s no DH, meaning he’ll take on eight actual hitters instead of nine and the National League has weaker lineups compared to those in the AL.

However, while pitching may come easier, Lester now has to bat, which hasn’t been pretty… or even decent looking.  He’s 0-for-50 career at the plate in the regular and postseason and has issues throwing to bases, something he will have to face in an NL that likes to bunt to move runners along (insert pitchers batting).

With young up-and-coming stars like Anthony Rizzo, Starlin Castro and top prospects Kris Bryant, Jorge Soler, Javier Baez and Addison Russell, and now the signings of manager Joe Maddon and now Jon Lester, the Cubs’ offseason commitment to returning to the postseason is no longer a question.  This will be a team to watch out for in 2015 and definitely in 2016.

The wait is almost over Cubs fans.

Next: Lester joins list of MLB's 20 richest players of all-time