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.

10 Responses

  1. Patrick Jeter

    I like that chart. Something you made? Or is that info hosted somewhere on the interwebz?

  2. Jeremy Conley

    Great article Wesley.

    The only part I would quibble with at all is in the last paragraph where you say “Epstein isn’t interested in convoluted stats just for the sake of convoluted stats.” To that I have to ask, who is?

    I feel like even giving credit to the idea that there are people out there that are making up complex but meaningless statistics just for the sake of being “modern” or whatever, is just the bias of people like Daugherty and Marty coming through. No one is doing that. All of the analytically-inclined GM’s and front offices are trying to gain an edge by looking at new information, or looking at old information in a different context.

    Theo may be better at it than other people, and why he is better is an interesting question. He talks about makeup, scouting, and medical information, so maybe his team does a better job at integrating all of that with performance analytics. Just a guess. Point is, it’s a question of being better at the same goal, not a question of different goals.

    I think we need to stop giving credence to this idea that some stats guys are just in it to make up numbers and confuse people, or whatever you were implying the motives are in someone who is interested in convoluted stats just for the sake of convoluted stats.

    • Wesley Jenkins

      Right, I agree with you wholeheartedly and was attempting to dismiss that notion with that line but completely understand the other reading. I guess specifying it to Epstein made it sound like there were people out there who did it for the sake of convoluted stats. Thanks for the comment!

  3. Patrick Jeter

    Cozart: 0-3 with 3 strike outs today from the leadoff spot.

    I’m guessing the whole thing about earning the right to hit 1st only applies to Billy and not Zack.

    I think I just threw up in my mouth a bit…

    • Patrick Jeter

      Meanwhile, Votto on base 2 times in his first 3 PA. In other news, the sky is confirmed blue.

  4. Michael E

    Two lopsided trades and piles of cash at his disposal. Those were the building blocks. Other moves were helpful, but Theo’s best move was picking the right team at the right time. The Cubs had hit rock-bottom, garnering a top draft pick and having the consensus best player slide to them (Correa looks to be great as well, so just fortunate two can’t miss types at the top). Our Reds are now at what the Cubs were when Theo took over…who knows, maybe we got our own Arrieta or Rizzo already.

    The Cubs also had the ability to field a payroll double that of the rest of the division based on revenues topped only by Yankees, Red Sox and Dodgers. That is a nice cushion, to know you can lure FAs or make trades with ample room for even more adds later.

    Buying low on Rizzo and Arrieta, two highly-regarded prospects that were either in a pitchers park putting up mediocre numbers or pitching in a hitters haven NL East, were the signature moves. Arrieta had the makings of an Ace already and there is little sense as to why the Orioles sold so low (think Jocketty trades this winter). It’s not like Arrieta was nothing and Epstein saw something in some obscure stat. Rizzo was also highly regarded, and bafflingly was traded twice in a year. These are the kind of moves even I could make and it really bothers me that Jocketty and Co don’t like trying to find highly regarded prospects that are scuffling and in need of a change of scenery. I would first check pitchers park teams for scuffling hitters and hitter park teams for scuffling pitchers and target those players. It’s not hard and I don’t need stats or analytics…just need to see a scouting report full of praises and an ERA north of 5 or a BA south of .220 to know this is a player we need to scout once more and initiate talks around…

    I wish we had a GM that would look for bargains and diamonds in the rough, instead we got one that looks for three times injured players or players past their prime that were never any good to start with… it doesn’t take an Epstein, but it does take common sense.

    • lwblogger2

      Makes sense but I will mention that the whole idea of “hitters parks” and “pitchers parks” started with analysis of how hitters performed at each park. This essentially was the analytics movement in its infancy.