Late Tuesday afternoon, semi-confirmed rumors (are there any other kind?) started to swirl that the Cubs had reached a basic agreement with the Red Sox to hire away from Boston one of the youngest and most-successful GM’s in baseball, Theo Epstein.  At the time, I was preparing a post for today that would broadly survey the careers of some key candidates in Tom Ricketts’ search for a new Cubs GM (Epstein included).  I’ve never been so happy to throw away an idea.

Try to mentally rewind to late August.  Remember some of the names that were thrown around in the days after Jim Hendry was fired?  Epstein was part of the conversation from the beginning, but with another year on his contract and the Red Sox sitting in good shape for the playoffs, he was not considered one of the prime candidates for the job.  He seemed firmly planted in the “wishful thinking” category, along with Brian Cashman, Andrew Freidman, and Pat Gillick.  In fact, he was perhaps the least-likely of those elite possibilities.

So you’ll forgive me if I feel the need to extend a hearty, long-distance pat on the back to Tom Ricketts* for accomplishing the near-impossible, or at least the highly-improbable.

*Just a side note about Ricketts–for more than a year now, it’s been hard to get a good read on what kind of owner he will be.  It was no surprise when he took over the team and didn’t immediately conduct a scorched-earth campaign to clean house–it’s clear he’s not Jerry Jones, Mark Cuban, or a Steinbrenner.  But his inactivity since those early days has looked to many–including me–like complacence.  What’s more, his defense of Hendry and Quade, and his quote about injuries being the only thing that held this team back from contention made him sound like a buffoon, and did not inspire any confidence in his fanbase.  I got a sense there might be more to him the day he fired Hendry, but it wasn’t until this week that I felt like he really might be showing his true colors as an owner.  What’s clear now is that he did really want to get an inside look at what was right and wrong with the team, and it seems like he’s taken his time not just to sit and watch, but to formulate a plan for success.  We’ll have to wait to see what the next step is, or if it will work.  For now it’s just reassuring to know the Cubs are heading in a new direction, and that Ricketts is committed to it.

And certainly it wasn’t all Ricketts’ doing–he had to rely on the alignment of stars well beyond his control to make this dream a reality.  The historic collapse of the playoff-bound Red Sox, the mysterious character assassination of beloved manager Terry Francona, the allegations of clubhouse antics and division, and the rampant overspending in Boston all conspired to bring Red Sox owner John Henry and team president Larry Lucchino to the tipping point where they were willing to part ways with GM-ing wonderboy and noted gorilla suit enthusiast Epstein.

Take it as a sign of Red Sox Nation’s speedy transformation from long-suffering loyalists to entitled front-runners that Epstein’s departure was met with anything less than weeping and gnashing of teeth.  After all, this is the guy who led Boston out of the perennial also-ran wilderness and into the promised land of two** world championships and routine playoff contention.  That he left town with little more than a collective shrug of the shoulders from Boston fans might be at least part of the reason he was ready for a change of scenery in the first place.

**Some naysayers will say “Nay,” pointing out that Epstein inherited a contending team that included Manny Ramirez and Pedro Martinez, and that his World Series victory is more a credit to the front office he replaced.  And while it’s true that he had many advantages in his first years with the Red Sox that he won’t enjoy with the Cubs, he did return to win another World Series with an overhauled team in 2007.  I don’t expect a dramatic one or two year turnaround, but I think it’s clear he knows how to build and sustain a winner.

Or perhaps Epstein just wanted a new challenge?  It’s hard to say for sure what could attract a guy like him–a Boston native who grew up in the shadow of Fenway Park and achieved the highest level of success in what may well have been his dream job–away from the deep pockets of the Red Sox and the fierce competition of the AL East.

What is sure is that the Cubs present some different challenges for Epstein.  He’s essentially starting from scratch, attempting to build a winning franchise from the ground up.  Matt Garza looks to be the anchor of our pitching staff moving forward, but he’s not Pedro Martinez.  And aside from budding superstar Starlin Castro, Epstein’s inheriting a collection of overpaid veterans and under-skilled role players.

The minor league cupboards might be just as bare.  To my knowledge, there aren’t many future Kevin Youkilises and Jon Lesters in the Cubs’ farm system.  Is it possible?  Certainly, but it’s hard to tell right now.  Player development has not been the Cubs’ forte since, well, ever, so it will take more than Epstein’s presence alone to get the prospect pipeline moving in the right direction.  Fortunately, Ricketts seems willing to pour additional funds and resources into the farm system.

But player development has been only one aspect of Epstein’s success in Boston.  He’s also clearly not afraid to spend big on the free agent market.  Many skeptical fans and sportswriters have already pointed out that Epstein’s free-spending ways with the Red Sox mirror some of the bad contracts handed out by Jim Hendry in the last days of the Tribune’s ownership.  In fact, you could make a case that Epstein’s signed far more bad deals than Hendry ever did, and you’d probably be right.

But I do see one significant difference between Epstein’s circumstances in Boston and the situation he’ll face here in Chicago: the absence of the Yankees.  When Theo said goodbye to the Red Sox earlier this week, he also said goodbye to the constant arms race of the AL East.  He won’t have the same pressure in Chicago to keep pace with the Yankees spending, and he won’t need to throw money at players to keep them out of the Bronx***.  I expect Epstein to be a little more selective with how and where he spends big, now that he’s not trying to operate in the shadow of the Steinbrenners.  Neither the Cardinals, Brewers, or Reds can compete with the money the Cubs can spend if they want to–and as long as they spend it wisely, I’m on board.  All that remains to be seen is how financially committed Tom Ricketts is to winning.

***The signings of Daisuke Matsuzaka and Carl Crawford in particular always seemed to me to be as much about bringing those guys to Boston as they were about keeping them away from the Yankees–which seems to be what you have to do to compete in the AL East (unless you’re the Tampa Bay Devil Rays and you draft high for more than a decade straight).

And it’s still too early to say what Epstein’s responsibilities will even be.  The initial reports were that he was coming over to the Cubs for a position higher in the organization than the one he had in Boston.  That might mean he will be the President of Baseball Operations, or something similar, and hire his own GM beneath him–possibly Josh Byrnes, Rick Hahn, or someone out of the Boston organization.

But none of that matters until the Cubs have actually signed Epstein to his reported five year, $15M contract.  The main holdup right now is over compensation for Boston.  In return, the Cubs want to give them cash; the Red Sox apparently want players, too (there’s a rumor that one of the players they covet is the reportedly untradeable Jeff Baker, which cracks me up for some reason).  Also still undecided is who Epstein will be allowed to bring with him to Chicago from his front office staff in Boston.  And there’s speculation that both teams are getting pressure from the MLB to slow things down so that Epstein’s official announcement and press conference can happen on a day without a playoff game–possibly Monday or Tuesday.

For now it appears things are in a holding pattern until there’s an official announcement from either team.  In the meantime, I’ve linked some key stories an articles below, and I’ll continue to update the links throughout the weekend as more news and details become available.

  • What do we know about Epstein away from baseball?  He’s a dad.  He’s a philanthropist.  He’s reportedly a hard worker and a genius–which is good news, because the Cubs need both.  And he’s a fan of Pearl Jam and fake mustaches, and reportedly followed them on a tour through South America during his brief hiatus from the Red Sox in 2005.  Maybe he can work it out with Eddie Vedder to play “Someday We’ll Go All the Way” at Wrigley Field after losses?  Maybe not.
  • Dave Kaplan tells the inside story on what Ricketts did and said to bring Epstein to Chicago.  Specifically, it sounds like some of Tom Ricketts’ recent moves–and the substantial money he committed to his draft picks this year, in particular–convinced Epstein that the Cubs’ owners are willing to do whatever it takes to win.
  • ESPN’s Gene Wojciechowski explains the cautious optimism felt by many Cubs fans, and asks some good questions about what we can and should expect from Epstein.
  • The Chicago Tribune’s David Haugh with some thoughts on what Epstein’s hiring says about Ricketts’ plans for the team.
  • Also from the Tribune, Phil Rogers takes a look at what led to the Red Sox/Epstein divorce, and why Boston might regret it.
  • In case you missed it yesterday, our own Dustin Godsey wrote up a nice to-do list for the Cubs next GM.
  • And here’s a link to Cubs page on, where you can usually find he latest rumblings on what’s going on with the Epstein situation, and the team in general.
  • UPDATE: Red Sox owner John Henry made a surprise appearance on a Boston sports radio station today to discuss a variety of topics concerning the state of the Red Sox.  His statements about Theo Epstein, which you can read in part here, made it clear Epstein has parted ways with the team.  In fact, Henry and team president Larry Lucchino were already talking in broad terms about parting with Epstein at least a day before the rumors of him joining the Cubs caught fire.  Why then is the transition still stalled?  Despite the fact that they’re already moving on without him–including a semi-announcement that team VP Ben Cherington is going to be the new GM–they still think they’re owed something in return for releasing Epstein from his contract.  They might just be dragging out the inevitable, or they might steadfastly believe they deserve a combination of prospects and cash in return for a GM they seemed set to fire earlier this week.  Either way, expect it to take into early next week before there’s any official announcement from the Cubs.
  • UPDATE:  Dave Kaplan with some further insight into the holdup on Epstein–essentially, Boston is dragging this out to make things difficult for Epstein.  The short article includes some scathing quotes about Larry Lucchino from an unnamed baseball executive.
Like what you see here? Never miss new content. Follow Us: