A few weeks ago, I, along with eleven other baseball nuts, created a dynasty fantasy baseball league meant to last for five years. Now, the idea behind the league was to draft once and never again. It would be a dynasty league in the truest sense of the word. I say this because a five-year dynasty league values one thing: highly productive players already in their prime or about to hit it.

This past Sunday, we held our inaugural (and only) draft. While drawing any sort of inference from the fantasy baseball draft of twelve college-aged baseball nerds is a ludicrous concept, I’m still going to do it. In the first 100 picks, the Cubs had the most players selected. The same for the first 50. In the first 20, only the Astros bested them.

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Considering that only one Red was drafted in the top 100 picks (Joey Votto), the Cubs preponderance of talent is all the more dismaying. The team currently fields six young, viable superstars (Kris Bryant, Anthony Rizzo, Kyle Schwarber, Jake Arrieta, Jason Heyward, Addison Russell), and that list doesn’t even include super-prospects Javier Baez and Jorge Soler or veterans Jon Lester, Dexter Fowler, and Ben Zobrist.

Is one fantasy baseball draft an exact science? No, of course not, but it is worth a look at how exactly the Cubs came about their current stockpile of talent.


On October 22, 2011, Theo Epstein—then general manager of the Boston Red Sox—resigned his post to take the job of Cubs’ president of baseball operations. Upon arrival in Chicago, Epstein inherited what Fangraphs considered the 22nd best system in the league, highlighted by can’t-miss prospects such as Brett Jackson, Trey McNutt, and Chris Carpenter (not that Chris Carpenter). The team had just drafted Javier Baez the previous summer, but all in all, the outlook on the farm was pretty abysmal. Even Chris Carpenter, the team’s number three-ranked prospect, was lost soon after Epstein’s hiring when the Cubs shipped the pitcher to Boston as compensation for Epstein himself.

To say Epstein built this current iteration of Cubs from the ground-up might actually be underselling the feat he accomplished. The Cubs were well into the process of digging themselves a grave under the cellar of the NL Central when Epstein took over, and after hitting rock bottom that season, it was a steady climb followed by one strong leap to the top.

So how did he do it? Well, first, not all the credit can go to Epstein. While he was the architect behind the Cubs massive overhaul, he needed some help. Hiring Jed Hoyer from San Diego to be his GM and Jason McLeod from the Red Sox to be his head of scouting and development, Epstein had the infrastructure in place to massively overhaul the Cubs’ system.

Over the next three seasons, Epstein made smart trades, implemented a doable draft strategy, and targeted high-value free agents (both on the field and in trade value).

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Take the deal for Arrieta for example. Half a season of Scott Feldman and a B-level prospect in Steve Clevenger got the Cubs the future NL Cy Young winner, a lockdown reliever in Pedro Strop, and some cash to boot. While giving the Cubs’ personnel all the credit in evaluating what Arrieta could become is a stretch, Epstein still assembled the team that saw value in the pitcher.

While Javier Baez was already in the system by the time Epstein was hired, the Cubs have done an outstanding job in developing their young talent. From Baez to Bryant to Schwarber to Soler, the Cubs have set expectations for their young players and seen them exceed those expectations time and again.

Before the 2014 season, ESPN did a profile of Epstein, hoping to answer the question of how he could remain so calm amidst the storm that were the miserable 2012 and 2013 seasons.

On the topic of the draft, Epstein told the reporter: “The currency of the draft is information. Scouting information, statistical information, makeup information, medical information. In each of those buckets, we have to drill deeper if we want to have an advantage.”

The answer reveals the underlying success factor driving Epstein’s tenure at the helm: modernization. By outfitting the organization from the scouts to the analysts and everyone in-between with the latest technology, Epstein and the Cubs have been able to exploit the simplest form of power.

When the Cubs hired him away from the Red Sox, Epstein was marketed as a new-age, SABR guy high on analytics and low on old-school technique. While that is accurate to a degree, Epstein isn’t interested in convoluted stats just for the sake of convoluted stats. He is simply seeking any new information that can give him a leg up, and guess what, it’s working.