The first book reviewed from the NHL Executive Reading List (click here to read about the list) is The Cubs Way by Tom Verducci (Amazon).

This book is on the Kyle Dubas (Toronto Maple Leafs GM) and John Chayka (Arizona Coyotes GM) lists and tells the story of the 2016 World Series Champion Chicago Cubs.

The Cubs Way described how Cubs President Theo Epstein rebuilt the franchise through data and analytics as well as a focus on finding quality people.

Here are my five key takeaways and a few notes on how they relate to the Toronto Maple Leafs and Arizona Coyotes:

(1) Epstein Believes More Information is Better

One of the ways NHL front offices differ from each other is in how they collect, process, and use information. While many General Managers believe that more information is better, some feel it’s more important to identify the right information.

Years ago, one NHL GM pointed to a competitor and told me, “they collect mountains of information. Stats, numbers, anything you can think of. Yet they never make a move. More info sounds great until you get paralyzed by having too much of it. We like to keep our front office footprint small and focus on the key pieces of information that really matter.”

Baseball executives differ as well. Cubs President Theo Epstein feels more information is better. Jed Hoyer, GM of the Cubs, said Epstein “believes in never having enough information and asking for more. It’s probably his best quality. It’s not about focusing on any one area, because if you do that you may miss the biggest piece of information.”

For the Cubs — and almost all sports franchises — it starts with the draft. Epstein said:

“We built our scouting department around the idea that the currency in the draft is information. That’s it. The currency in the draft is not, I’m a little bit better of a scout than you. We’re going to have great scouts. We’re probably going to have some that are not so great mixed in. You don’t know it. It takes years. But the currency of the draft is information.”

The Coyotes posted a behind-the-scenes video of Chayka leading up to the 2018 NHL draft and he also said “we view the draft as an information game.” Chayka is big on understanding a player’s mindset. For example, Chayka said that during interviews with prospects at the Draft Combine he’s “looking at how they say things as much as what they say.”

The Cubs look at scouting information, makeup information, and medical information.

Epstein sees scouting as a numbers game. He wants the Cubs to have more scouts than the competition. He wants them seeing the right players and he wants his scouts seeing them more often. Those are all elements you can optimize over time with investment and appropriate feedback loops in place.

When it comes to makeup of players, he wants his scouts to go beyond a check-the-box exercise. A comment like ‘good kid’ isn’t enough.

“I saw it a hundred times”, Epstein told Verducci. “‘Good makeup. Good kid’. Tells you nothing. Explain. Everyone’s life is really complicated and involved and there are myriad influences and background factors and transformative experiences and challenges and times when they responded the right way to adversity and times they responded the wrong way. And you have to dig and figure out what makes this person tick and how he’s going to respond in pro ball.”

Epstein got his scouts to adapt by asking them to find three examples of how a player responded to adversity on the field and three examples from off the field. The exercise forced scouts to do their homework and dig deeper than surface level descriptors, but it also helped to screen for “how he’s going to respond in pro ball.”

The Cubs were also facing a century-long history of disappointment and failure. Fans and media alike would take aim at the team with the first sign of trouble each season and Epstein wanted to build a team capable of sticking together and responding positively to that inevitable adversity.

And scouts weren’t the only source of information. Cubs catcher coach Mike Borzello told Verducci:

“With Theo you always feels like he knows he has people working for him who can be a resource, who know people, like if you want a background check on somebody. He asks ‘What’s his personality like? What’s it like when things are going good? What’s it like when things are going bad?’”

Epstein also wanted medical information. He worked with a company called NeuroScouting during his time with the Boston Red Sox and retained a semi-exclusive partnership when he made the move to Chicago. NeuroScouting offers a computer program that assesses how quickly hitters process information. Epstein tested his current players and then used the results to benchmark against the neural makeup of potential draft picks.

The Cubs took a similar approach with the biomechanics of pitchers. After signing big-ticket free agent Jon Lester, Epstein said Lester’s “mechanics rate” was higher than anybody else they’d seen tested by their biomechanical labs. He added that Lester had also been on a “state of the art shoulder conditioning program since he was 18.”

All of this information allowed the Cubs to mitigate against the obvious risk of signing a pitcher in his 30’s to a big-dollar, long-term deal.

(2) Asset Management

Not surprisingly, the Cubs leverage data and analytics to drive a lot of their research but they also acknowledge that numbers alone can be deceiving. Epstein has processes in place such as a “Change of Scenery” survey to find qualitative insights.

After each season, Epstein asks his scouts and baseball operations people to:

“…submit a list of names of major and minor league players they believed would flourish with a change of scenery and why. Clashes with a manager, problems at home, an injury kept quiet, a positional logjam — anything could be holding back a player that didn’t show up in traditional metrics.”

The 2012 survey unearthed 2015 Cy Young award winner Jake Arrieta and illustrates Epstein’s buy-low philosophy to asset management.

When it came to acquiring franchise cornerstone Anthony Rizzo, Epstein said at the time “Hey this is a 21-year-old who struggled his first couple of months seeing big league pitching. Great. That’s exactly when you can get him.”

After another trade, Epstein said “A year from now, we’d never be able to trade for a guy like that, not without paying a heavy price. We try to get these guys before they are household names.”

Comments like these show that Epstein didn’t suffer from paralysis by analysis — he was aggressive when it came to pulling the trigger after identifying an undervalued asset. But I also noticed comments sprinkled throughout the book that the Cubs took a “safe route” to rebuilding. That they chose to buy “bonds instead of stocks”. It seemed inconsistent.

Fortunately, Verducci did a great job describing how the Cubs staff approached their rebuild. After reflecting on the book, I realized that the Cubs didn’t have a single approach to filling the holes on their roster. And that was by design.

I expected to read about Epstein’s long-term vision of stockpiling as many assets as possible to win at some undetermined point in the future, but instead he was very focused on the five-year window that aligned with his own contract. Epstein used that as a constraint and then charted a path to success by Year 5.

Tank for a few seasons as a strategy to stockpile enough high draft picks to fill the entire roster? Nope. The Cubs’ research showed that most players — even first rounders — take too long to mature and contribute at the major league level.

Follow the widespread trend (at the time) of drafting high-upside pitchers? Too much risk and too hard to predict which ones would boom and which would bust.

Open up the wallet and build the roster through free agency? Maybe for a player or two, but the inherent nature of free agency is overpayment. How were the Cubs going to consistently lure the biggest names to Chicago without blowing through the luxury tax thresholds?

None of those strategies alone provided a predictable path to Year 5 success. Yet I noticed that all of those strategies — when applied selectively to specific portions of the roster — provided unique opportunities to fill holes.

The Cubs decided to focus on drafting and acquiring young position players first. While pitchers offered more upside, they also came with more downside risk. So in this case the Cubs “bought bonds instead of stocks,” as Hoyer described.

They started by building a core of position players — Rizzo, Kris Bryant, Kyle Schwarber, Addison Russell, Albert Almora — before turning their attention in the later years to pitching via trades and free agency.

Verducci mentioned that the Cubs used 11 pitchers in the 2016 World Series and every one was acquired from another organization.

The Toronto Maple Leafs seem to be following a similar strategy as they build around a young core of forwards like Auston Matthews, Mitch Marner, and William Nylander. This summer they decided to supplement that core by signing John Tavares to a $77 million free agent contract.

Dubas said that the difference between their pitch to Tavares and their unsuccessful pitch to free agent Steven Stamkos in 2016 was that the Leafs are at a different stage as a franchise:

“If you rewind it two years ago, we were going in and saying, “Here is what we are going to become,” and, “Here is what we intend to be.” It was selling somebody or trying to sell them on what we intend to be as an organization that had just finished last place and took first overall, versus now in 2018, “Here is who we are, here is what we are about, here are who the players are.” It was much easier.”

Dedicating $11 million of annual cap space to a free agent heading into the back half of his career is a big commitment, but the opportunity to grab Tavares was unique. Players with his combination of talent and work ethic almost never become available via trade.

That doesn’t mean the Leafs will go back to the free agent market to fill their holes on defense though. Like the Cubs, expect Toronto to utilize the trade market to find cost-controlled Top 4 defensemen that fit their cap situation and stage in the competitive cycle.

[Update Jan 28: Leafs acquired Jake Muzzin from LA. Muzzin is signed through 2020 at $4M cap hit]

(3) Screening for Character

During the initial interview process in Chicago, Epstein told Cubs owner Tom Ricketts, “I don’t know what you think I am, but I’m not what people think I am.”

Epstein was probably referring to his reputation as a Moneyball-era analytics whiz kid. A cold-hearted disciple of Billy Beane who makes decisions by staring at spreadsheets, not into the eyes of his players.

But one of the biggest themes in the book was the Epstein and the Cubs’ focus on character and the human element. Epstein explained:

“I used to scoff at it, when I first took the job in Boston. I just felt like, you know how we’re going to win? By getting guys on base more than the other team, and by getting pitchers who miss bats and get groundballs. Talent wins, but…it’s like every year I did the job I just developed a greater appreciation for how much the human element matters and how much more you can achieve as a team when you have players who care about winning, care about each other, develop those relationships, have those conversations. It creates an environment where the sum is greater than the parts.”

Verducci described two reasons Epstein began to change his perspective over time.

In Boston, Epstein surprisingly traded Nomar Garciaparra because Boston’s “proprietary defensive metrics showed Garciaparra to be among the worst shortstops in the league.” At the time, Garciaparra was also taking heat in the media over a contract dispute and the negative attention was starting to impact the team. After trading Garciaparra, the Red Sox went on a roll and Epstein started to realize how much a negative vibe could impact performance of the team on the field.

Epstein also realized that any competitive advantage obtained through new analytics or proprietary technology would be fleeting. “Interestingly, during the push for the next competitive advantage and how flat everything’s gotten now and how smart everyone is, and how everyone is using basically the same technology, I feel like I’ve pushed our organization back to the human being,” he told Verducci.

Epstein said the process of screening for character starts with the draft:

“That’s the one time all year when you decide proactively, affirmatively, what type of person, what kind of human being, you want to bring into your organization. When you trade for players, you can only trade for those who are available. It’s a small subsection of players. When you’re signing free agents, you can only sign those free agents who are available — a very small percentage of players who are available. In the draft, when it’s time for your pick, the entire universe of players is out there for you. You choose one of them. Whether you sort of admit it or not, you’re saying ‘this is what I want my organization to be. This is what I want my organization to be about. This is a Cub.’ Every time you pick, especially in the first round, that’s what you’re saying.”

(4) Cultivating the Environment

Verducci spent a considerable part of the book studying Joe Maddon, a fascinating manager who joined the Cubs from Tampa Bay in 2014. At the time, the Cubs had just rebuilt their minor league system and restocked their prospect pool by trading away any major league asset with value.

But as the talented prospects approached the major league level in Year 3 of the rebuild, the Cubs desperately needed to reshape the MLB clubhouse environment.

Enter Joe Maddon. While the scouts and baseball operations staff continued to focus on acquiring players with strong character, it was up to Maddon and the coaching staff to create a “workplace environment that promoted growth.”

Maddon and Epstein instituted Individual Player Development Plans to offer players actionable feedback and promote shared accountability.

Shared accountability also came in the form of no dress codes (Maddon encouraged themed outfits for road trips to lighten the mood), less meetings (only three per year with positive messages), and minimal rules. Retired catcher David Ross said Maddon “builds a foundation on just doing the right thing. He establishes an atmosphere where you have a choice between right and wrong, and you choose right. You don’t need rules for that.”

The Cubs also spared no expense when it came to upgrading the facilities at historic Wrigley Field.

GM Hoyer said “one of the things [owner] Tom Ricketts focused on was that if we were supposed to be a first-class organization then we would have to make sure we took care of everything for the player. If they feel that we take care of every little detail for them, then all they need to do is go play. The more we can do for them has value as far as showing we care about them and their families as people.”

Hundreds of millions of dollars went into facility upgrades. Epstein established a mental skills department with experts dedicated to helping players deal with the psychological aspects of the game (and sounds a lot like the Leafs’ Wellbeing & Performance role established in August 2018)

Hoyer said “In some ways we went overboard, making sure that they knew that this isn’t about the Cubs anymore. You are going to be treated great and have the best of everything.”

What does Hoyer mean by overboard?

Consider this incredible example from Verducci: “Between the batting cage and the dressing area is a designated “party room” where the Cubs immediately celebrate wins as soon as they come off the field. The lights dim, electronic dance music starts to play, strobe lights and smoke machines fire up, and videos with the star of the game begin to play. The players dance, sing, chant, and splash bottles of water on each other.”

(5) The Curse of Success

The investment obviously paid off — players raved about the new facilities and the Cubs won the World Series in 2016 — but it begs a question: how sustainable is that advantage?

Sure, players who were on the team in 2015 ahead of the Wrigley renovations noticed a huge difference. Players coming from outside the organization benchmarked the Cubs’ facilities against their previous teams’ and were obviously impressed.

But we all fall victim to the hedonic treadmill — “the observed tendency of humans to quickly return to a relatively stable level of happiness despite major positive or negative events or life changes.”

It’s human nature. Today’s party room is yesterday’s hot tub. We can’t help but take our fortunate circumstances for granted over time and the 2016 World Series champion Chicago Cubs are probably no exception.

In fact, Epstein himself acknowledged that unrealistic expectations after winning the 2004 World Series in Boston eventually drove him to Chicago: “We were just getting too big. When we won, our fanbase grew, our revenue grew, the expectations to keep creating revenues grew, our expectation for winning 95 games and getting deep into playoffs grew every year.”

Epstein admits that he failed to stick to his principles in the face of adversity and started to manage his team in Boston with emotion. “I thought the 2010-11 offseason was me, for the first time, taking the easy way out, giving in to the environment. It’s easy to sign guys to seven-year deals. It’s hard to find guys that are more creative value solutions or plan ahead a couple of years.”

So that’s the challenge that now faces the Cubs.

Verducci quoted a handful of players throughout the book that were chosen by the Cubs because they “would do anything to win a World Series.” What happens after you win that elusive World Series? What happens after a “disappointing” 95-win season in 2017.

I guess what makes people like Epstein, Maddon, and most professional athletes successful is they’re obsessively committed to winning.

Hoyer said that the “beauty of Theo” is “after we won the World Series we were right back to work doing something Saturday and Sunday right before the GM meetings.”

No time to celebrate. No pause to appreciate the accomplishment. Right back on the (probably top-of-the-line) treadmill.

It’s tough to be hungry after you’ve already eaten.

Next Review: Astroball by Ben Reiter