At this time last year, Joel Sherman (New York Post) crowned Chicago Cubs President of Baseball Operations Theo Epstein as the most interesting person in MLB.

After all, he had a lot on the table heading into last season, and was looking to make history once again:

“Theo Epstein solves historic problems. He was the architect who put The Curse and Bill Buckner into the past in Boston. If he does the same for The Goat and Steve Bartman in Chicago, well, the waiting period for Cooperstown should just be waived.”

Well, Epstein lived up to the honor in 2016 by delivering the Cubs’ first World Series championship in over 100 years. This year, however, he has a different goal: Create a dynasty. And that target once again makes him one of the most fascinating people in all of baseball.


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But before we get into the list itself, I want to bring up a broader point. We often discuss a potential Cubs dynasty in the making, but it really isn’t that easy of a target to reach. In fact, it’s fairly abstract and undefined. For example, the Cubs have averaged 100 wins over the last two seasons, have twice made it to the NLCS and have won the World Series. In addition, they’ve had three Cy Young Finalists (plus one winner), four Gold Glove Finalists (plus two winners), an MVP, a Rookie of the Year, and a Manager of the Year award. That is a TON of hardware and accomplishments.

If they (as a team) were to somewhat keep up the pace in 2017 – let’s say, another NL Central victory with 90+ wins – and reach the NLCS for a third straight year, would that be considered a dynasty (at least in its early stages)? If they add another MVP award and a few more Gold Gloves to the mix, is it a dynasty then?

In other words, how long and how good do the Chicago Cubs have to be, in your opinion, for the dynasty tag to be appropriate? (I’m really asking.)


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In my gotta-set-the-bar-somewhere opinion, you probably have to make the playoffs four (or maybe five) out of five seasons, with at least a few really deep runs (and at least two Championships). In that regard (and considering the 2017 projections), the Cubs are well on their way, but do still have plenty of work to do.

Fortunately, they have the right man, Theo Epstein, for the job and he, too, wants to see a dynasty begin to take shape in Chicago. In any case, that pursuit of greatness is what makes him this year’s 6th most fascinating man according to the New York Post. And he wasn’t alone from the reigning world champs.

Epstein was joined on the list of MLB’s 50 most fascinating, according to the New York Post, by three members of his World Championship Chicago Cubs. Here’s how they all shook out.

Chicago Cubs on MLB’s 50 Most Fascinating:

  • Theo Epstein #6 (Previously: #1)
  • Jake Arrieta #10 (unranked)
  • Kyle Schwarber #19 (unranked)
  • Kris Bryant #41 (unranked)

Not a bad showing, for a list that includes players, managers, executives, and other MLB officials.


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You should head over to the New York Post for more (after all, the list as a whole is interesting, even without the Cubs connection), including why each person made the cut.

You already know that Epstein made it due to his quest for a dynasty, but Arrieta (last season before free agency), Schwarber (his heavily-anticipated return), and Bryant (on a quest of his own (to become the game’s second best player)) have compelling write-ups of their own.

In addition, the list features others like Rob Manfred (3), Shohei Otani (11), Tim Tebow (14), and many more. Definitely worth checking out.


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