In 2008, the Chicago Cubs won their second straight division title. It wasn’t like its predecessor, though. That 2008 title was a matter of course. That Cubs team was dominant. They won 97 games, led the National League in runs scored by 56 and finished second in runs allowed. Seven Cubs batters had above-average OPS figures, and of the 10 Cubs who saw significant time, nine had an OBP of at least .358. Of the 14 pitchers who pitched most for them (one of whom was Jeff Samardzija), only one (Bob Howry) had a worse-than-average ERA.

The Dodgers swept that 2008 team out of the playoffs in the first round. It was the second straight season in which the Cubs reached the playoffs, but failed to win a game there. The 12-game improvement the team made between 2007 and 2008 meant nothing in another short series.

This failure broke my father’s spirit. He just snapped. Look, my dad was never foisting Bill James books on me, but he was a relatively reasonable Cubs fan (a reasonable Cubs fan, without the qualification of relativity, is either a myth or a vulgarity) for the first decade of my fan experience. We would go to a few games each year, revel in Wrigley Field, track the rumor mill relentlessly, always be chatting about the players changing places, the farmhands the team was hyping, and why none of it worked. My dad grew up in the dark days of the mid-to-late-1970s, and had grown accustomed to just accepting the Cubs for what they were, long before I was even born.

The 2003 and 2004 seasons materially changed Cubs fan culture. Winning became an obsession for millions of fans who had treated wins as incidental for decades. By the end of the team’s 2006-07 spending spree, Cubs fans were pretty much just like Yankees fans—only sadder. My dad and I fell right into line in that regard. Thus, when the 2008 team folded in October and the dream began to die, my dad reeled for a while.

“I’m sick of it!” he might say. “Sign Bonds to be a pinch-hitter. Trade for Roger Clemens and put him in the bullpen! Just win, already!”

That’s not an exaggeration of any kind. At a certain point, the Cubs drive you insane, and when that happens, it isn’t pretty.

In truth, though, the Cubs have never done anything remotely like signing Barry Bonds. As a Cubs fan who has only known the more competitive version of the team, the version that pushes for the playoffs at least every few years, the version that ran a $144-million payroll in 2009, it surprised me to go back through their recent history and see so few truly impactful free-agent signings. Sure, they gave Alfonso Soriano $136 million, but that was widely considered an overpay right away. The fact that Soriano signed before Thanksgiving is almost all you need to know. Beyond that, Chicago has been in play for a few elite free agents, but has never actually brought one in.

Well, anyway, they hadn’t until Tuesday. In what certainly can’t be called a rushed process or a bidding war against themselves, the way Soriano’s was, Jon Lester joined the Cubs. When you read this, Dad, take heart: this is the dawn of a totally new day. The Cubs are heavyweights, maybe for the first time in my lifetime, and it’s no longer up for debate.

In conjunction with the trade that brought in Miguel Montero earlier on Tuesday, the Lester deal sets the Cubs on a path toward contention right away, in 2015. After three years of struggles, Lester had a bounce-back season in 2014—maybe even a career year. He pitched like a legitimate front-line starter throughout this past season, and the Cubs are counting on him to deliver that kind of performance going forward. For more detail on how he made his comeback in 2014, check out this piece on his evolving approach to right-handed batters, and this one, on the change in the release point on his curveball. You can judge the likelihood of Lester continuing his dominance for yourself, after reading those articles.

Whether Lester will pitch like a star, though, matters less than the fact that he’s now a part of Chicago’s mix. He’ll enter the season as their top starter, with Jake Arrieta second; Jason Hammel third; Kyle Hendricks fourth; and the winner of a competition fifth. That competition on the back end will be between Tsuyoshi Wada, Travis Wood, Edwin Jackson, Jacob Turner, Dan Straily and Felix Doubront. Chicago might even look to fill that final slot with a moderately big-name addition, but whether they do so or not, they have ample pitching depth. Lester adds a presence at the top of the rotation such as the Cubs haven’t had since the mid-2000s. He also makes the team good enough to be worth doubling down on, which means the front office will look to add another significant piece or two this winter. Major additions like this one, especially when out of character for the signing team, always have trickle-down effects.

It’s not just the rotation that will be strong. With Montero in tow, the Cubs have the makings of a young, powerful offense, with two All-Stars (Anthony Rizzo and Starlin Castro) anchoring a very deep, balanced core, and tremendously talented prospects on the cusp of making the lineup really coalesce. The bullpen was a bright spot even on last season’s 73-win team, and has gotten stronger now that we know one or two would-be starters will be able to take up residence there. The Cubs aren’t ready to truly challenge the Cardinals in the NL Central, but they have enough remaining money and enough depth in their farm system to change that before Opening Day.

None of this is stirring analysis. Sorry about that. I’m a Cubs fan, a weary one just now, and I have already done thousands of words of work on Lester from that analytical standpoint, and at this moment, all I want to say is: The Cubs are very real. They’re a legitimate force in the marketplace, maybe for the first time ever. And they’re going to win sooner than anyone thought, a year ago. My dad has reason to celebrate.

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One Response to “Jon Lester Sends the Cubs Soaring”

  1. Matt's Dad

    Celebrating here! Very exciting Cautiously optimistic.
    Exceedingly proud. Of the Cubs as well…


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