Theo Epstein-When Does He Cash In On His Prospects?

Theo Epstein and the Chicago Cubs find themselves with a lot of top prospects. Most will never see any time in Chicago. The time is nearing when he needs to decide when to cash in and get the rebuilding Cubs back into the playoffs.

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Chicago Cubs

Theo Epstein is in his fourth year of his Chicago Cubs rebuilding program. According to that plan, it would take five years to turn the Cubs into playoff contenders.

Well, that plan may be a year ahead of plan. Even though they are 11.5 games behind the St. Louis Cardinals in the National League Central, they are only 1.5 games behind the San Francisco Giants for the last Wild Card spot.

During his rebuilding plan, Epstein acquired a lot of top-flight prospects. Some experts (like Baseball America), have the Cubs’ minor league system as the best in baseball.

Even with Kris Bryant, Addison Russel and Jorge Soler on the major league roster now, there are still plenty of highly rated prospects. Javier Baez, Kyle Schwarber, C.J. Edwards and Albert Almora are just some of the players who are almost ready to make an impact on the major league level.

One thing to know is that a lot of those prospects in the system will never wear a Chicago Cubs’ uniform. There are just too many prospects and not enough open slots on the major league club to have all of them eventually come up.

That leaves Epstein with some assets to work with.

The next phase of the rebuilding plan involves dealing some of those prospects. The thing is, when do you start shipping them out?

“No doubt, there is a timing element to it,” general manager Jed Hoyer said of moving prospects. “We haven’t been in the position to move a lot of prospects. We’ve been in a position to go out and get them. But as we move forward, you can wait too long and a guy loses his value.”

The Cubs are facing the New York Mets starting Tuesday. The Mets are a team fighting the Cubs for a playoff spot, and they also have some young players they can deal with. They have so many very good pitchers on their staff they are considering going to a six-man pitching rotation.

Pitching is a need for the Cubs. Some think the two clubs could make a deal with what they have. The Mets need offense, something the Cubs have. Starlin Castro and Baez are two names mentioned in possible deals. Perhaps even Schwarber could go to New York.

The Mets have Matt Harvey, Noah Syndergaard, Jacob deGrom, Jon Niese and Steven Matz. One or more of them can help the Cubs’ rotation.

Epstein feels keeping a lot of the prospects can be helpful as well. “The Braves almost created a dynasty out of evaluating their own players the right way,” he said. “Everyone they traded didn’t pan out. Everyone they kept won a lot of pennants.”

So there you have it. There are a ton of prospects Epstein and Hoyer have to work with. The question is, do they start using them before the July 31st deadline, wait until next year, or hold onto them and try to win with nearly ALL of them?

Epstein’s rebuilding plan has been difficult, but this next phase may be the most difficult part of the plan. We will see if he makes the right choice.

Next: Cardinals Show Chicago Cubs How Much Further They Need To Go

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