Could Red Sox players be following Theo Epstein to Chicago? – Inside the Wheelhouse


Theo Epstein Chicago CubsThe most recent era of Baseball being played in Boston since 2004 is now officially over as both Terry Francona & Theo Epstein have left the Red Sox Nation, departing from the organization since their collapse in September.

The devastation the September collapse of an 8-21 record & missing the playoffs after a 9 ½ game lead on September 1st in the Wild Card has prompted new changes for one of the best franchises in all of sports. While an era that brought two World Champions in eight years to a Championship stricken franchise since 1918 is now over, the slate is wiped clean in Boston and a new era must be built.

The rebuilding process for the Boston Red Sox will be done in the coming months as a new manager will be named and a new GM will be put in place. Free agents will be signed and players will be traded. Come time for Spring Training the Boston Red Sox should be poised once again for a run in the AL East. But the move that their now former general manager Theo Epstein isn’t as concrete at the moment as he heads to Chicago to end another famous sports curse.

[adinserter block=”2″]Epstein has a very similar task to what he took on with Boston in 2004. That is, to end a curse placed upon a Baseball franchise and bring a World Championship to a team that hasn’t seen one since 1908, a 103 year span that has seen two World Wars, television & technology to evolve and eighteen U.S. Presidents from Theodore Roosevelt to Barack Obama.

They are Baseball’s, Chicago’s and quite possibly America’s loveable losers. As they are “cursed” by Billy Goats, Black Cats and a Bartman. This is an uphill climb for the two-time World Champion General Manager, one that probably Epstein salivates at the mouth for if past history deems to ring true. If for Theo Epstein to become successful he will become a legendary Baseball General Manager, a future Hall-Of-Famer and quite possibly the best front office executive of all time.

Movies would be made, books would be written, fathers would be telling their children about the “great” Theo Epstein for centuries. You really can’t blame him for leaving Boston after all, while there is a horrible taste in the mouths of the fans he left behind, the times are “a-changin” in beantown and it was time for him to leave the great Baseball city for another great Baseball city. Now that the bags are packed and the deal is signed, what other Red Sox could be joining Epstein in the friendly confines of Wrigley Field?

I’ve put together a list of both Red Sox & Cubs free agents as we near closer to the MLB off-season as well as notable free agents that may end up as “Cubbies” as well:

Red Sox Free Agents:
– David Ortiz (1B)
– Marco Scutaro (2B/SS) (2012 option)
– Jason Varitek (C)
– J.D. Drew (OF)
– Tim Wakefield (SP)
– Jonathan Papelbon

Cubs Free Agents:
– Carlos Pena (1B)
– Aramis Ramirez (3B)
– Ryan Dempster (SP) (option)
– John Grabow (RP)
– Rodrigo Lopez (SP)
– Kerry Wood (RP)

Free Agents of Interest:
– Prince Fielder (1B)
– Albert Pujols (1B)
– Johnny Damon
– Roy Oswalt (SP)
– Heath Bell (RP)
– Jonathan Broxton (RP)
– Matt Capps (RP)

Let’s start by looking at the Red Sox that could be leaving Boston and join forces once again with Theo Epstein in Chicago. Of the six names, four of them could very well end up as Cubs with one player possibly being a back-up option if certain other free agents aren’t signed while one free-agent Red Sox player most certainly won’t end up in Chicago.

The four players that I could see leaving Boston to re-join Theo in Chicago are as followed: Jonathan Papelbon, Jason Varitek, Marco Scutaro & J.D. Drew.

Papelbon is the favorite out of the four to be leaving Boston for Chicago because he will be highly demanded on the current reliever market and the Cubs need a shut down closer for their team. Carlos Marmol led the league in blown saves and W.H.I.P. for closers in 2011, who knows how many wins the Cubs could have had if Marmol actually shut down the 9th inning for a victory. Signing Papelbon moves Marmol to a setup role where there isn’t as much pressure to win the game and the Cubs can let free-agent Kerry Wood go out on the market.

Up until September, it was almost a foregone conclusion for most of 2011 that Papelbon’s time in Boston was probably up. It appeared Daniel Bard was going to become “the man” for Boston in the 9th until his ERA fluctuated in the 6’s during the month of September. While Papelbon wasn’t as amazing, he still in considered to be one of the best closers in the game. Certainly Papelbon will be one of the highest priorities for Theo in the off-season to bring to Chicago.

The days of Jason Varitek being a starting catcher are over with and he has now assumed more of a role as a back-up catching mentor for younger catchers. While the American League may suit him the most since he can bat as a DH or catch on off days, he will be a primed target for a guy like Epstein who knows what Varitek can bring as a leader in the clubhouse and a mentor for a young catcher like Geovany Soto. Varitek provides depth at the catcher’s position, gives the Cubs a good person for the locker room and some who will serve as a mentor. He is a veteran leader that can help stabilize this young Cubs team.

As for Marco Scutaro I don’t see the Red Sox picking up his option for 2012 as Jed Lowrie appears to be the shortstop of the future for the Red Sox. Scutaro is a great defender in the field and someone who could serve as a good second baseman for Sterlin Castro at short. Scutaro also has a decent bat in his hands as well and can serve as some good depth towards the bottom of the order for the Cubs should Epstein reach out to his former signing.

Finally you have J.D. Drew; his time in Boston is most certainly over as it appears to be JJ Reddick’s time in Boston. Drew isn’t the player he once was or primed to become, but he is a veteran who will command a small amount of money after getting paid so highly over the last couple of years. I would not be surprised if J.D. Drew shows up as a right fielder for the Cubs on opening day.

Then you have the one Red Sox player who could be signed if other options for the Cubs don’t fall into place in the off-season. That player is free agent 1B/DH David Ortiz. Ortiz is a long shot to land in Chicago especially if Albert Pujols, Prince Fielder or Carlos Pena (in that order) doesn’t sign with the Cubs in the off-season to play first base. I fully expect one of those three to be in a Cubs uniform next season, Fielder more than Pujols.

Ortiz is your typical American League hitter as he would be better served as a player in a designated hitter role, hence why I believe he is a long shot. But should any of the first baseman I named pass the Cubs by and Ortiz is still on the market, I wouldn’t be surprised if he should sign. I don’t think Ortiz is heading back to Boston as a new era is coming through so you never know.

One Red Sox player that won’t be a Cubbie in the off-season is 45 year old starting pitcher Tim Wakefield. If Wakefield plays it will be for the Red Sox and no one else & for the Cubs to sign him would make no sense. I expect Wakefield to re-sign or retire during the off-season, playing for the Cubs are not an option.

All of this can become true if one thing were to happen, a move at the manager position which is currently held by Mike Quade.

Let’s get this straight; Terry Francona will eventually become the manager of the Chicago Cubs, just not this season. Francona will sit out the 2012 season, lick his wounds, take care of any personal problems he may have, become an analyst for some network but he will be back come 2013 and it will be with the Chicago Cubs.

Theo Epstein does not want to wipe everything clean with his new broom in 2012. The Cubs won’t win a World Championship in 2012, Epstein wasn’t able to pull that off in 2003 in his first year with the Red Sox either. But come 2013, like 2004 for the Red Sox (his 2nd season with them), I expect the Cubs to compete for a World Champion and to do so with a new manager.

Epstein & the Cubs front office will let Quade play out his contract with the hope of their sights set on Francona come 2013. Unless Quade takes the Cubs to the World Series in 2012 will he stay in Chicago, he is a sitting duck and knows it, simply warming a position that will be eventually held by Francona. Knowing that Francona could end up as the manager for the Cubs could very well sell most of Epstein’s former players in Boston go to Chicago.

Other potential moves I see Epstein possibly doing is re-signing Aramis Ramirez to stay in Chicago, who was trade bait at the deadline but wanted to play in Chicago, hence why he used his no trade clause to block any potential deals (that’s always a good sign). Picking up the option on Ryan Dempster for 2012 since the starting pitching is in flux and possibly re-signing Kerry Wood to fulfill a 7th or 8th inning role should they sign Papelbon & move Marmol to 8th or 7th.

Pena, Grabow and Lopez will be let go to free agency & I believe Epstein will look to trade former All-Stars Marlon Byrd and/or Alfonso Soriano to another team to get rid of those contracts. The 2013 Free Agent list would have some stellar outfielders like Josh Hamilton & Matt Kemp available should they not be extended & let out into the market. I would not be shocked if Epstein makes a deal during this offseason for B.J. Upton either.

[adinserter block=”1″]While one era closes in Boston another one opens in Chicago with the hopes of similar results. Epstein certainly has the ability to put together Championship teams and looks to do so in windy city for the next five years. Look for the puzzle pieces to be formed with former Red Sox players from teams he built in the past and the former head of the “idiots” to be at the helm in the dugout.

Reverse the curse part deux has begun in Chicago…

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Jeff Peck is the producer for the “Wheelhouse Radio” program that airs every Sunday at

Jeff also co-hosts “The Still Real to us show” with Eric Gargiulo which can be available at and can be downloaded in the “Real Guy Radio” section of the site.

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  1. The Cubs are welcome to any stiff of that roster with the exception of Petey and Ellsbury

    Theo makes them a playoff team in 2 years


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