The Theo Epstein Era and Machiavelli’s “The Prince” – A Comparative Discourse

“Is it better to be loved or feared?” Niccolò Machiavelli, The Prince

Leadership is a funny thing. To describe it is difficult, but you know it when you see it. In today’s baseball world there’s plenty of leadership taking place. However, that leadership is not always going in the right direction. The Cubs’ current leadership has them on the cusp of something special. Over the past four seasons, Theo Epstein has built this team into one that is a favorite for a World Series Championship in 2016.

Going to the Cubs Convention always provides an interesting look at the fanbase. There are some fans who have bought into what Epstein has been doing to build a winner. Then there are those who preferred the Jim Hendry method of spend, spend, spend. And then there’s the Sun-Times trying to do whatever it is they do.

When I arrive at the convention in less than a month, I expect it to be filled with fans who are excited at the thought that the Cubs legitimately have a chance to win big in 2016. The architect of that hope has been Epstein. I expect that he’s probably going to receive some nice ovations in the session on Saturday morning. I don’t think people fear Theo, but I know many fans just now beginning to love him.

As a teacher of world history, one of the most exciting periods to teach is the late medieval or early Renaissance period. Out of this era comes a book that explains the dynamics of leadership. Much as Sun Tzu’s The Art of War was for generals, Niccolo Machiavelli’s The Prince is for politicians and has been adapted for leadership in the business world. When comparing the latter text to the reign of Theo Epstein, one can clearly see several quotes outlined in Machiavelli’s treatise that pertain to what the Cubs have been through over the last few seasons.

theoprince“It must be considered that there is nothing more difficult to carry out, nor more doubtful of success, nor more dangerous to handle, than to initiate a new order of things.” 

When Theo came aboard in the fall of 2011, many Cubs fans were ecstatic with the hire. Though he had won two World Series titles as general manager of the Red Sox, the boy wonder had fallen out of favor with ownership over the signing of several high-priced free agents and a chicken-and-beer extravaganza in the clubhouse during the playoffs.

From the beginning of his Cubs tenure, Epstein faced skepticism for coming to a team that had not won a World Series since 1908 and had not been in one since 1945. From the start, he had a plan and was transparent in laying out what the Cubs would need to do to rebuild the franchise.

For the better part of 30 years, Cubs fans were used to the general manager going out and getting free agents and trading away prospects to acquire major league talent. Because the team was burdened with some high-priced contracts and a minor league system devoid of prospects at the upper levels, Epstein began a total overhaul. It was clear from the get-go that these were not going to be your old Chicago Cubs. Epstein was going to strip it down and rebuild it from the bottom up.

“The first method for estimating the intelligence of a ruler is to look at the men he has around him.” 

One of the first things that Epstein did was restructure upper management. He was named President of Baseball Operations and Jed Hoyer was named General Manager. In addition, Epstein brought in Jason McLeod as Vice President and Director of Scouting along with Joe Bohringer as Director of Pro Scouting.

McLeod and Hoyer had previously been with Epstein in Boston before they went to San Diego to run the Padres. Bohringer had been a scout for the Mariners and Diamondbacks organizations and had a degree from MIT, a perfect example of the blend of baseball and analytical aptitude the new Cubs regime would stress.. In addition, several other Boston front office executives came to join Theo, including data analysts and scouts.

This team would not be run as before. Scouting would play a crucial role in selecting both major and minor league talent. New terms such as WAR, on-base percentage (OBP), and fielding independent pitching (FIP) became buzzwords for players’ abilities. This was going to be a new way of doing things.

Some fans and writers didn’t understand. They lashed out in anger at Epstein from 2012 through 2014. They didn’t understand the rebuilding of the salaries being paid to major-league players. They didn’t understand the restocking of the minor leagues. They could only see the tip of the iceberg, not what was underneath. The expectation was that Epstein was a great evaluator of talent and he would sign the right guys in free agency to come play for the Cubs. They expected a $200 million payroll filled with free agents.

I remember distinctly sitting in the 2014 Cubs convention and listening to fans complain about the major league product. One fan asked why they should spend their money on season tickets for a team was going to lose close to 100 games in the coming season. Theo told the fan that he was not going to tell him how to spend his money, which I inferred as, “If you don’t want to spend the money on the tickets, then don’t come.”

Tommy Giglio/US Presswire
Tommy Giglio/US Presswire

“Men intrinsically do not trust new things that they have not experienced themselves.”

I think these attitudes bled over into the mainstream press as well, specifically the Sun-Times, many of whom didn’t understand exactly how this was all going to work. Luckily for them, bloggers were listening to Theo at every opportunity. Where there used to be a few blogs about the Cubs prospects, now there are dozens upon dozens.

A lot of the press that came out and began to analyze Epstein solely based on major-league performance from 2012-2014 missed the boat entirely about what he was doing. I think the best way to sum it up was that the major outlets didn’t understand that when Theo said he was going to do A, B, and C, he really meant that he was going to do A, B, and C. The press expected him to lie to them and go do D, E, and F instead.

Over the course of the last three years, many fans turned to blogs to get their information about the Cubs and their minor league system. In fact, many readers are now much more well-informed by “outsiders” than by people who are in the clubhouse every day. Those fans see players come up through the minor leagues and develop via alternative media, MiLB.TV, and even going to see minor league games. As a result, many of the major newspaper carriers have been passed by because they continue to do things the old way.

“Men will not look at things as they really are, but as they wish them to be—and are ruined.” 

Just as Sun Tzu espoused the art of deception in war, so too did Machiavelli when it came to politics. I don’t think Epstein necessarily rules that way. He’s quite clear about what he wants to do, but he’s going to do it his way. He’s not going to overpay for the centerfielder, starting pitcher, or a reliever this offseason.  He knows the limits when it comes to what he is willing to part with and when. It doesn’t have to be this winter. I think the big thing to remember is that if you can’t get a player at a price you’re willing to pay in the winter, you might be able to get that same player at a better deal in the summer.

This offseason, Epstein only used three players — Starlin Castro, Wander Cabrera, and Frandy Delarosa — to bring in major league talent. He has kept all of the Cubs’ top 30 prospects in the fold. He’s gotten Jason Heyward, Ben Zobrist, and John Lackey without surrendering any player assets.


“Everyone sees what you appear to be, few experience what you really are.” 

With the rise of fantasy baseball, many fans think they know how to run a team. But that’s just not the same as what Epstein does, not even close. Selecting 25 top players in a 10-12 team league every year is easy. Trying to sustain winning in the majors over the course of a decade against 29 other teams is extremely hard.

What Theo Epstein has done is truly remarkable. It took the Pirates and Royals almost 20 years to rebuild their teams through the draft. Epstein has done it in four. And I don’t think most fans truly know what he has done in rebuilding the organization in terms of players, scouting, and analysis. They only see the product on the field.

Maybe that’s as it should be. Part of Machiavelli’s treatise is to guide the Prince to sustained success – to hold on to the power, not just get it once. Still, many Cubs fans still can only see winning once. Theo Epstein sees an organization designed to have the chance to win every year. That’s why he is the Prince.

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