Is Epstein the answer? Cubs’ fans and doubters like myself are going to find out, well maybe. According to multiple reports the Cubs have agreed to a 5-year, $20 million deal with Epstein. The only thing that’s holding up the deal is the compensation for Epstein. Why not ask for everything if you’re Boston?

I would if I were Boston. I would ask for Starlin Castro and Andrew Cashner since the Red Sox have all the power in this deal. Those names are the two that have been mentioned by multiple MLB sources.

A lot of sources within the Cubs organization are throwing caution to the wind about the compensation aspect possibly shutting this deal down, which lets the conspiracy theorist in me surface. What if this is all a “wag the dog” by Tom Ricketts and the Cubs? How so?

It’s now reported everywhere that everything has been agreed upon in this deal except for the compensation to the Red Sox for Epstein, so Ricketts has done his job now it’s how cooperative the Red Sox are going to be to get this deal done. Excuse the following cliché, but the Red Sox brass can be the “scape goat” for Epstein not coming to Chicago, and the Cubs getting a more affordable option that can do just as good of a job if not better.

Of course, if Ricketts is as big of Cubs’ fan as he’s billed himself then a big name like Epstein is exactly what he wants, names are what matters on the North Side. Look where that’s gotten Cubs? Two big name managers with a good amount of talent and no World Championships. I know it was time for Jim Hendry to go, but the more I look at the teams he put together for the Cubs I become more sympathetic towards him.

The reason I would not be happy about Epstein if I’m a Cubs’ fan is that Epstein won championships in Boston with his predecessors’ players, not his own talent. Epstein did supply some key pieces to the puzzle, David Ortiz, Kevin Millar and Curt Shilling, but he’s also the same GM that signed players such as J.D. Drew, Daisuke Masuzaka, and John Lackey to bloated, unnecessary contracts. He also signed Andrew Miller and added injury-prone Erik Bedard in an attempt to help a depleted Red Sox starting staff. Bonehead moves such as these lead to the ultimate collapse of the Red Sox this September. The Cubs need more than key pieces to the puzzle to make a serious play for the NL Central.

Those signings seem no better then what the Cubs had with Jim Hendry or what the White Sox have with Kenny Williams. A lot of bloated over paid contracts for very little in return. How about Carl Crawford and Adam Dunn, both seemed worth the money, both were 2011 busts. Is Theo Epstein another Kenny Williams? It seems that way, but Epstein’s had even more money to spend then Williams, so he has the bonus World Championship. Which brings me to my final point.

What will Epstein be able to do for the Cubs with bloated contracts and a limited budget? That’s the $20 million question that would worry me the most.

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