Landing Lester Signifies Cubs Readiness to Win Now

“It’s not often you get to win the lottery. We won the baseball lottery. It’s up to us now to put it in effect.” – Cubs Manager Joe Maddon.

Jon Lester was the Golden Ticket of the 2014 off-season. The prized lefty seemingly entertained more suitors than Penelope after the Trojan War. The Cubs came out victorious, beating the Red Sox, Giants and Dodgers, among others, to secure Lester’s services.

What’s so strange about the outcome is what the other three franchises have in common that the Cubs do not: success. Boston, San Francisco and L.A. have reached the postseason a combined eight times from 2009-2014, including four World Series titles. The Cubs on the other hand have missed the playoffs the past six seasons and finished with a losing record the past five.

The Cubs were clearly the odd-man out in that group when it came to on-field success. Yet Lester, who could have gone anywhere he wanted, chose Chicago. Why? We can’t discount the money, a reported $155 million over six years, including a $30 million signing bonus. The total could go up to $170 million with a vesting option for the 2021 season. The Giants offer for Lester added a guaranteed seventh year around $168 million. Boston’s offer was considerably less at six years and $135 million.

But let’s be honest. This is Monopoly money territory. A few million dollars when you are already up private-plane range is negligible.  If money was the only thing that spoke to Lester, he would’ve taken the highest guaranteed cash in the San Francisco deal, knowing that at almost 31 years old, this would be his last major contract. If comfort and familiarity was the deciding factor, Boston would have made the most sense as he played almost his entire career there, and he has said how much he loves the city and fans. But Lester chose Chicago. The North Side became a destination for a high profile free agent for the first time since Alfonso Soriano signed with the club in 2006 (hopefully this deal works out A LOT better than that one did).

Lester’s signing represents a fundamental shift in not only where the Cubs rebuilding plan is headed, but how players perceive the plan. Cubs President Theo Epstein is always the smartest guy in the room and his relationship with Lester dating back to their Boston days undoubtedly played a role in signing the ace. But the ultimate pitch to Lester would have been simple: come to Chicago to make history. Because we are ready.


Theo Epstein has preached patience since taking over the Cubs reigns in 2011.
His plan continues to head in the right direction.

Patience has been the hardest part. Not only for the fans (after all, 106 years of losing means patience is basically a sixth sense), but I’m sure for the front office, too. Theo Epstein arrived in Boston in 2003. The Red Sox broke the curse of the Bambino a season later. He helped them win the World Series again in 2007. There was no “rebuild”, just a hefty remodel based on Sabermetric principles that Epstein and Co. were some of the first to adopt.

When Epstein took over on the North Side in 2011, bringing trusted confidant Jed Hoyer over from San Diego to be his GM, the Cubs had just finished back-to-back losing seasons for the first time in six years, and things were only going to get worse before they got better. That’s not easy to say to a franchise as mired in futility as the Cubs. We are more than worn out by losing, and you are going to promise us even more? “Wait Till Next Year” became “Wait Till Five Years From Now, Then We’ll See.” It is a hard sell anywhere, but especially on the North Side.

Epstein, however, created hope out of the bleak immediate picture. He had the Wunderkind charm and winning pedigree, but even more so than his personal accolades, he had this: a plan.

“There are no shortcuts in baseball,” Epstein said in his introductory press conference. He wasn’t going to lie to fans or hide the truth; the next several years were going to be more about building for the future than winning in the present. There would be a light at the end of the tunnel, but it would involve an Andy Dufresne-esque trudge through 500 yards of shit-smelling foulness to get there.

Cubs fans often feel like Andy Dufresne trying to escape their fate through a dark tunnel of crap.

That meant three-straight seasons of 89+ losses and attendance that dipped to 2,642,682 in 2013, the lowest in 15 years. It meant passing on high-profile free agents and selling off some of your best players mid-season. But through all the meaningless late-summer afternoons on Clark and Addison, hope persisted. Hope with names like Rizzo, Castro and Bryant. Soler, Baez, Russell. Almora, Alcantara, Schwarber. Hope suddenly looked less like a Christmas wish list, and more like a lineup card smattered with home runs, gold gloves and high on-base percentages. And to quote “Shawshank” once more, hope is a good thing, maybe the best of things.

But if the batting order looked like a future all-star team, the rest of the foundation had holes to cover up. The first fix came last month when Joe Maddon fled Tampa Bay for the Windy City, offering to buy everyone drinks upon arrival. Many in baseball view the quirky, cerebral Maddon and his trademark thick-rimmed glasses as the best manager in baseball. It was a huge, unexpected coup for the Cubs, and they knew it. The rebuilding timeline suddenly shifted. The manager was in place, the young hitters would be ready to steadily make waves in the majors; all that was missing was a top-of-the-line ace to lead a pitching staff with emerging players like Jake Arrieta and Kyle Hendricks. Enter Jon Lester.

Joe Maddon is fit to lead the Cubs to their first World Series since 1945.

In the aftermath of the Steroid Era, baseball is flush with dominant pitching. Top-of-the-line hitters are suddenly at a premium. So Epstein and the rest of the Cubs brass rightfully stockpiled their minor league system with bats, using first round picks on Kyle Schwarber (2014), Kris Bryant (2013), Albert Almora (2012) and Javier Baez (2011), signing international studs Jorge Soler and Arismendy Alcantara, and trading last year’s ace Jeff Samardzija for top prospect Addison Russell.

The method to the Cubs madness was simple: build the farm system back up with as many quality hitters as possible, knowing that impactful bats are more difficult to come by through free agency and trades because teams are locking up their young hitters with long-term deals (see Stanton, Giancarlo). But since the game is overflowing with solid arms, the surplus meant you could always go buy a pitcher when the time was right. It would surely cost you, but the Cubs play in Chicago, not Milwaukee. They are in the third largest market in the country, and money should not be an obstacle. So after carefully and frugally knocking down the team’s walls (both figuratively and literally) and managing their money like a small-market club, the time to break out the pocket books arrived.

That’s what the acquisition of Jon Lester signifies. It means the Cubs can immediately field a competitive ball club for the first time since 2009 and the long road toward relevancy has arrived. Look, the Kansas City Royals went from missing the playoffs for 29 straight seasons to making the World Series. With the added Wild Card team, one-third of the league now makes the playoffs. There is no reason to believe the Cubs can’t compete for a postseason spot THIS season. 2015 used to be a pipe dream. 2016 and beyond was always the realistic target. But with Lester, Maddon, the young core of hitters ready to burst onto the scene and maybe another major move or two this Winter, the Cubs’ “plan” has accelerated up a year, if not more. Nothing needed to be compromised to get here. Chicago just became a landing spot for some of the best at their respective positions in the game.

“Every opportunity to win is sacred,” Epstein said when he addressed the Chicago media for the first time 38 months ago. Will the Cubs suddenly make a Royals-like jump to the World Series? In just one year, that’s highly doubtful. Not every move will pay off. Not every young stud will pan out. But the opportunity to win is finally here.

After waiting as long as Cubs fans have, the Promised Land may be closer than we think.


Posted on December 10, 2014, in Cubs. Bookmark the permalink. Comments Off on Landing Lester Signifies Cubs Readiness to Win Now.

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