Here we sit at the end of June, the Cubs having lost almost twice as many games as they’ve won and basically the worst team in baseball by the numbers, and a question keeps coming to mind.

What was Theo thinking?  What was it about taking over the Cubs’ baseball operations that appealed to him?  What pushed him to take the job in spite of the obvious and plentiful hurdles to immediate success?  Even as the situation in Boston disintegrated around him, what prompted him to Chicago?  What made him think this kind of humiliation and frustration would eventually be worth it?

I think there are a variety of answers, and they might give us downtrodden fans some encouragement as the Cubs race to what could be their worst-ever record.

We can start with the easy answers.  History certainly was a factor.  Coming to the Cubs gives Theo an opportunity to figure heavily in the ending of the two longest championship droughts in the MLB for two of its most popular teams.  That alone would put him on the league’s Mt. Rushmore.  That he also would get  to oversee the preservation/renovation of the two oldest and most beloved ballparks in baseball would be gravy, and (to mix metaphors), only further knit him into the fabric of the game.

But those couldn’t be the only reasons.  Those are a dreamer’s reasons for taking the job–they’re the reasons you and I, or any lifelong Cubs fan would sign up in a heartbeat.  I’m not convinced Theo is that kind of dreamer.  Or at least, that he would make such a leap and take such a risk based solely on those dreams.  He seems to be too smart and too practical to whimsically chase glory and immortality like that.  And he knows too much about the game to think it would be that easy.  There has to be something more to it–something tangible and concrete on which he could build those historic championship dreams.

Maybe it was money?  Not money for Theo–although I’m sure he’s well compensated.  I’m talking about the Ricketts family’s deep pockets.  Theo knows you don’t buy your way into consistent relevancy in baseball, but it takes money to stay there.  The Cubs are one of the most profitable brands (although it makes my skin crawl to talk about the team in those terms) in baseball, and winning only drives up their already nationwide popularity.

The problem that the Pirates and the Royals have–where they develop talent but can’t afford to keep it long enough to build a winning team–that won’t ever be a problem for the Cubs.  And with the renovation of Wrigley and the transformation of Wrigleyville on the horizon, the Cubs can expect to be even more profitable as the team grows.  Theo enjoyed the comfort of financial flexibility in Boston–he wouldn’t have come to Chicago if he didn’t expect the same thing here.

But it wasn’t just the money, either.  As I said, Theo knows you can’t buy your way to the World Series every year, and my guess is that he’s still a ways off from making his first big free agent splash (I’m not counting Jorge Soler, since that was more like spending big on the draft than stealing a proven free agent off the open market).  The Cubs aren’t one player away from the playoffs, and so right now it doesn’t make sense to pay anyone like he’s the guy who will take us there.  The Cubs’ payroll now is significantly lower than it’s been in years–if they’re really going to lose 100 games, I’m sure Tom Ricketts wants to keep it that way.  At least for now.

Add to that the new restrictions on paying draft picks and international free agents, and those deep pockets become even less motivating on their own.  Sure the Cubs might not ever have serious money problems, but they also have fewer avenues to spend that cash and spend it wisely.

Which makes me think that there was something else besides history and financial flexibility that made Theo think he could turn the Cubs into a winner.  As odd as it sounds with our current dearth of talent, I think he must have seen a player (or players) on the current Cubs roster who he thinks he can build on.

He’s certainly aware of what Matt Garza’s capable of, having faced off against him in the AL East for years.  And while the contract negotiations with Garza’s camp haven’t born any fruit, I’m not willing to assume Theo only sees his ace as trade bait.  But Garza wouldn’t be the only guy, since you can’t build a strong foundation solely on a guy who only plays every five days.

Who else?  Maybe Theo’s a Jeff Samardzija believer, and already has him penciled in to our starting rotation for the next few years?  Maybe he’s super high on Javier Baez, Dan Vogelbach, or some of the other draft picks we picked up last season?  Maybe he sees something in Josh Vitters that the world hasn’t seen yet is just now getting a glimpse of?  Maybe he knew he could reunite with Anthony Rizzo, and he’s got astronomical expectations for him, too?  I can’t tell you which pieces Theo thinks he can build on, and which he sees as placeholders.

I can tell you that when he came to the Cubs, he was intrigued by Starlin Castro’s talent–and who wouldn’t be?  Castro’s abilities are attention-grabbing (as are often his mistakes).  If you had to pick any team in the league, you’d pick the one with the 22 year-old phenom with barrels of raw talent and a potentially long, bright future ahead of him.  There are only a handful of those kinds of players in the league right now, and I’m sure that factored into Theo’s choice to come to Chicago.

However, it wasn’t until lately that he was sure he could build on him.  Like everyone else, Theo had his questions about Castro’s maturity and his discipline.  It wasn’t until Theo saw him up close and watched Castro work to improve his game that Theo was sure he was a keeper–that he was a building block and not trade bait.

What was Theo thinking?  I think it was some combination of the reasons I’ve listed.  I think he saw a few players who exhibit the kind of talent he can build on.  I think he knew that when the time came to spend money, he wouldn’t get hand-wringing or push-back from Tom Ricketts.  And I think he knew that despite some of the obvious flaws that need to be addressed, the Cubs are an organization he can eventually turn into World Series champs.

And frankly, the fact that an outsider who doesn’t need the headache and heartache of the Cubs would look at the mess we have on our hands and see that… that gives me hope.

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