The Plan: Epstein, Maddon, and the Audacious Blueprint for a Cubs Dynasty

I want to dedicate this book to my late father, Marshall. Because without his love of baseball and the love of sports that he instilled in me and my brother at a young age I would not be doing what I’m doing today. Hey Dad, can you believe it? The Cubs won the World Series! I miss you and I love you.

Contents

Foreword by Anthony Rizzo

Special Introduction by Allan H. Bud Selig

Author’s Note

1. Tom Ricketts and the New Cubs

2. Worse Than They Thought

3. The GM Job

4. The Money—Mesa, Wrigley, and the Rooftops

5. Getting Theo

6. Building the Best Front Office in Baseball

7. Doubting the Plan

8. The Arrieta Trade

9. The Odd Arrival of Joe Maddon

10. Jon Lester Takes a Leap of Faith

11. The Three-Headed Monster

12. 2015—The Kids Are Ahead of Schedule

13. 2016—That Magical Year

14. There Never Was a Curse

15. Celebration Time in Chicago

Afterword: The Inside Story of What Went Wrong After 2016

Appendix I. Cubs Drafts of Amateur Prospects, 1994–2011

Appendix II. Partners and Sponsors

Appendix III. List of Critical Clauses in Rooftop Contract

Appendix IV. Theo Epstein’s Letter to Red Sox fans

Appendix V. Tom Ricketts’ Letter to Fans

Acknowledgments

Photo Gallery

Foreword by Anthony Rizzo

Being a part of the Chicago Cubs’ first World Series championship team since 1908 will be an experience that I will cherish for the rest of my life. To get to this point, however, our team had to go through a lengthy overhaul that involved the entire franchise. I made my debut with the Cubs in 2012, and those early days were incredibly tough. That year we lost 101 games, yet as soon as I joined the team I could feel a positive vibe throughout the organization. I just knew that the Cubs were in the process of building one of the best teams in Major League Baseball.

I truly believe that the Chicago Cubs are one of the most incredible organizations in the entire world of sports. With the Cubs, it all starts right at the top with Tom Ricketts and the Ricketts family. They give us everything that a club needs to be successful and that is all you can ask for from ownership. Our front office, headed up by Theo Epstein, Jed Hoyer, and Jason McLeod, are proven winners and they have built the best team in baseball by adding great young players who play like veterans and outstanding veterans who play like youngsters. I am confident that the mix of talent that we have will lead to many more winning seasons and hopefully several more World Series championships.

David Kaplan, who has been around our team for over 20 years, gives the reader a real perspective of how the Chicago Cubs were able to go from being called the lovable losers to the best team in baseball. We ended a drought of 108 years without a World Series title and we did it by playing for each other and playing for our fans and the city of Chicago.

When we arrived in Mesa, Arizona, in February 2016, our team knew what we could accomplish and what was expected of us. Our manager, Joe Maddon, told us that we had to meet those expectations head-on. Thus, our mantra, Embrace the Target, was born and we did just that all season long. We got off to a 25–6 start and we met every challenge along the way against tremendous competition. Although a 162-game season is a grind, every player who wore our uniform, our coaching staff, and our front office never took our eyes off of the ultimate prize, winning a World Series championship.

This is an accomplishment that many didn’t believe could happen. It did happen, and this is David Kaplan’s story of how he watched us become champions.

—Anthony Rizzo

World Series champion and three-time All-Star first baseman,

November 2016

Special Introduction by Allan H. Bud Selig

The author, David Kaplan, has masterfully captured the drama of one of baseball’s most compelling stories, the resurgence of the Chicago Cubs over the past few years. Mr. Kaplan, a distinguished and popular Chicago sports broadcaster, artfully describes how a franchise, known as the lovable losers for its unparalleled record of futility that had existed for more than a century, is transformed into the World Series champion.

After 108 years of despair, dating back to the Cubs’ previous World Series victory in 1908, hope, which had been the allure that had driven fans to root for the Cubs in the first place, no longer is fleeting, if not rare. It is now so abundant and thick that you can reach out and touch it. The unbending loyalty of Cubs fans is remarkable. And they are not just from Chicago. There are Cubs fans everywhere, in every corner of our great country. Finally, they have been rewarded.

As it should be in baseball, the players receive and certainly deserve the bulk of the credit when a team is successful. But in the case of the Cubs, a great deal of credit is also due to the foresight and vision of the Ricketts family and especially the Cubs’ chairman, Tom Ricketts.

This is Mr. Kaplan’s story, one that began more than a decade ago, when Tom Ricketts, a die-hard Cubs fan, first had his eye on the purchase of the Cubs. During the summer of 2006, before the Cubs were even for sale, Tom, knowing he would need the approval of his family to make his dream come true—particularly his father, the patriarch of the family—threw a giant family party across four rooftops facing Wrigley. Before the day was out, he had convinced his father and the rest of the clan that owning the Cubs would be good for the Ricketts.

The author describes how Tom spent the next few years working behind the scenes to buy the club. Finally, in 2009, the family’s purchase of the Cubs from the Tribune Company came to fruition. As Commissioner, I recognized the value of the Ricketts family and knew it would be a positive influence on the game, and was instrumental in gaining baseball’s approval of the sale. The Cubs had just completed a season in which they had finished out of the playoffs. That, unfortunately, began a streak of five consecutive losing seasons and Cubs fans surely felt like it was—in the immortal words of Yogi Berra—déjà vu all over again.

But through the next few years, Mr. Kaplan reports, Tom had begun working on a long-term plan for rebuilding the club as well as rejuvenating Wrigley Field. As a former owner of the Milwaukee Brewers, I know how difficult it is to build a ballclub from the bottom up. It takes a great deal of intelligence, creativity, hard work, and patience—not to mention a bit of luck. After enduring several difficult seasons, Mr. Kaplan details how the Cubs began to turn it around following the 2011 season. That’s when Tom made the first of his brilliant front office hires, bringing Theo Epstein to Chicago from the Boston Red Sox as the Cubs President of Baseball Operations.

Even before his purchase of the Cubs, Tom had begun to reach out to me, usually for advice and historical perspective about the game. After the 2011 season, it was clear he was looking for a general manager. According to the author, Tom had already conducted a study of every franchise’s minor league system and their draft records to determine who was signing and developing the best young talent. In his view, that franchise was the Boston Red Sox—and Theo Epstein was the reason.

It turned out that Theo was ready to move on after a decade in Boston. Once Tom got permission from the Red Sox to talk to Theo and made his pitch, I got involved as an intermediary in the discussions between the two clubs and helped make it happen. The hiring of Theo caught a lot of people in baseball by surprise. Theo had been a fixture in Boston. Hired as its general manager in 2002 at the age of 28, he became, at the time, the youngest GM in the history of the game. Theo was an immediate success and became a legend overnight when the Red Sox won the World Series in 2004, his first season with the club. It was Boston’s first World Series victory in 86 years and finally brought to an end the curse of Babe Ruth that had plagued the club and the city for all those years. In 10 years with the Red Sox, Theo’s club won two World Series championships and reached the playoffs six times.

As Mr. Kaplan describes, it wasn’t going to be easy for Theo to duplicate that kind of success in Chicago. He and his brain trust began putting together the pieces, player by player, over the next few seasons. But he needed the right person to run the club on the field, and that person was Joe Maddon, who joined the Cubs as manager prior to the start of the 2015 season. And they haven’t looked back since. Joe had significant success as manager of the Tampa Bay Rays even though he had to deal with the financial constraints that all small market clubs must deal with.

And now the Cubs have pulled off a miracle just as historic as the one Theo was instrumental in pulling off in Boston. There, Theo helped erase the Curse of the Bambino, and, in Chicago, he helped dismantle the Curse of the Billy Goat. This one is equally as momentous, if not more so, and will bring the same kind of joy and happiness to loyal and patient Cubs fans that those fans in Boston experienced a dozen years ago.

David Kaplan has done great work in putting this story together, focusing first with the arrival of Tom Ricketts and his family and then with the arrivals and contributions of Theo Epstein and Joe Maddon. But, more importantly, as a longtime Cubs fan, David has lived through and certainly understands the pain and torment that Cubs fans have endured over many, many decades. He appreciates the import of the moment now that the Cubs have erased 108 years of futility and recognizes that it is joyously welcomed by all Cubs fans, those who are present and, in spirit, those who are gone.

—Allan H. Bud Selig

Former Milwaukee Brewers owner (1970–1992) and MLB Commissioner (1992–2015),

November 2016

Author’s Note

What would possess a man to take nearly a billion dollars of his family’s fortune to buy a baseball team that is the worst in the league, has a stadium that is going to need nearly $700 million worth of renovations, and has spring training and Latin American facilities that are also substandard compared to most of Major League Baseball?

Add in that the man and his siblings, wife, and children would also go from an extremely comfortable life of privilege, a life that they have enjoyed without a hint of public scrutiny, to a life where their every professional move would be second guessed by a fan base as large as any in all of professional sports and an intense media throng who cover the team on a 24/7 basis.

In addition, the political dealings to renovate the most iconic stadium in American sports will be as difficult a process to navigate as any transaction the family has ever had to endure throughout their professional lives. There will be opportunities to move the team out of its famous stadium, battles with politicians and neighbors alike, all hoping to capitalize on your team’s success to line their pockets.

To top it off, the deal to buy that baseball team will be so complex that it will hamstring the franchise for several years as they attempt to completely overhaul the organization from top to bottom all the while knowing that their failures will be splashed across the sports pages on a daily basis.

Once they would assume control of the franchise they would find an organization that was out of touch with the way most of Major League Baseball conducted its business. The Cubs were behind in so many areas Tom Ricketts and his family would have no idea where they should begin. The infrastructure was far below major league standards. The computer age had arrived and left the Chicago Cubs in the dark ages. Plus, most importantly, the talent level from the minors to the major league roster was so deficient that the future was exceptionally bleak to even the most die-hard fan.

That’s how strong the lure of owning the Chicago Cubs is, the lure of being the one to end the longest championship drought in sports history. A franchise known as the lovable losers, with all of its warts, had many billionaires lusting to own it. One bidder emerged on top, paying $845 million for the challenge of winning a World Series.

However, it would take time, there would be hundreds of losses and last-place finishes along the way and there would be many days the fan base and the media would question if the owners were committed to winning. Many would wonder if ownership was willing to spend what it would take to rebuild the franchise and to field a championship caliber team.

This is the inside story of how the Chicago Cubs went from laughingstock and a team called the lovable losers to World Series champions and the envy of all of Major League Baseball.

1. Tom Ricketts and the New Cubs

"Buying the Cubs in 2009 was like buying a house after a great party. There’s empty pizza boxes, empty beer cans everywhere, and some guy you don’t know sleeping on your couch. Then you realize, I didn’t buy the party, I just bought the hangover."

—Tom Ricketts, 2016

Owning a professional baseball team is a dream that many young men have as they go through their childhood and formative years playing Little League and participating in fantasy baseball. What baseball fan hasn’t romanticized what they would do if they owned their favorite MLB team?

We all think we would make better decisions than the current management and we all think it’s easier than it really is. For Tom Ricketts, the dream to own a team started at a young age. The dream really has two levels, he told me in his Wrigley Field office in June of 2016.

There are really two levels—the fantasy level, which I always fantasized about and in fact, my business school essay was about me wanting to own a Major League Baseball team. As a kid I was a baseball fan and then when I became an investment banker and trader I got into some fantasy baseball leagues and I started reading Bill James and all of his abstracts and I really got into it. I lived across the street from Wrigley Field and my dream job became owning a major league team.

Then there is the second level that Ricketts spoke about, and that is when you have the assets to legitimately entertain the notion of owning a baseball team. With his father having started T.D. Ameritrade and the entire family experiencing tremendous financial success, the dream of owning a team suddenly didn’t seem so far-fetched. Being the astute observer of the financial world that he is, he had his eyes on the Cubs more than a year before the team hit the market.

From a family standpoint it was a once-in-a-lifetime opportunity. If it happened and if we didn’t act upon it then we would be kicking ourselves for having missed a golden opportunity. My company, Incapital, was going very well but I was traveling on business all over the world and I was looking for a way to step back and be around home more. Owning the Cubs would keep me just as busy, but instead of being in Hong Kong, London, or somewhere else, I would just be down the street, so to speak. In fact, before I ever talked to my siblings and our dad I sat down and talked about it with my wife, Ricketts said.

At this point in time it seemed a mere pipe dream that the Ricketts family could win the bidding for the Cubs if the franchise even hit the open market. However, taking a run at the Cubs was exactly what Tom Ricketts was planning to do.

I told my wife I might think about running this out and seeing how it goes. She gave me her blessing but I’m sure running the calculus in her head she probably thought this has no chance of ever happening. Then I talked with my dad, who is not a big sports fan. He was not excited about it at first but we have this family trust that is fairly inert. It just sits there. I said to him that we should have the family trust be one of the bidders, Ricketts said.

However, at this point the Chicago Cubs were not yet up for sale. There were rumors about that possibility and there were reports of financial problems throughout the Tribune Company. In fact, the Tribune was eventually headed towards bankruptcy and needed to liquidate assets, with the Cubs as one of their most valuable properties. But, that part of the equation was still a ways away.

It was late 2005 and I remember hearing through my contacts in the financial world that the Tribune was looking for a private equity investor. They needed somebody to put a slug of money into their company and this was all pre Sam Zell. However, the typical financial return profile that a private equity investor is looking for is either you sell it in a few years for a large multiple or you get some type of excellent cash flow that makes it very valuable. A baseball team has neither of those. You don’t take any cash out and they don’t appreciate at a rate that a private equity investor would have interest in. It is an investment that only appreciates years down the road, Ricketts explained to me.

As that process began to unfold it was still a long way away from seeing the Chicago Cubs with a for sale sign on the franchise. And, it was still more than a year away from an eventual sale of the Tribune Company to maverick Chicago billionaire Sam Zell.

Then, in August of 2006, we threw a giant party on four rooftops because that’s what we do, the Ricketts throw giant parties, he joked. However, that day swayed Joe Ricketts, the patriarch of the family.

My dad had never done anything like having a party on a rooftop and he loved it. He told us it was much cooler than he had ever imagined. The Cubs weren’t very good that season but the park was packed, as were all of the rooftops. The vantage point that we had, you could see the whole neighborhood, and my dad’s buy-in was this was pretty amazing and it looked to be a good investment. My siblings were a lot easier to convince, but that day on the rooftops it was all just an idea because the Cubs weren’t for sale. I just knew what was going on in the financial world and what I was hearing about the Tribune Company and from that point the process took three more years to buy the team.

Where does one start when they want to buy a baseball team and where does one start when that team isn’t even on the market yet? Before the team was ever up for sale we flew out to New York to see our bankers in the fall of 2006 and we hired Sal Galatioto, who is the president of GSP [Galatioto Sports Partners], who became our sports banker. Then we met with the sports partners at Lehman Brothers and we told them we wanted to retain them as well to help us buy the Cubs. All of them told us the Cubs weren’t for sale and I told them, okay, they are not for sale but if they go up for sale—and I believe they will be—we want to hire you to help us buy them, Ricketts told me.

With Ricketts looking ahead to what he believed would happen as the Tribune faced mounting pressure to liquidate some of the company’s assets, he and his siblings put a plan in motion so that when the Cubs did hit the market they would have a jump on what was sure to be a large field of interested and well-funded groups who all wanted a chance to pursue the Holy Grail of winning a championship with the Chicago Cubs.

So we actually signed up our bankers in November or December of 2006 and the team didn’t hit the market until April of 2007. I just knew what was going on with the sale of the company to Sam Zell and with the financial structure of his deal that unless there was a miraculous recovery in the print media world, I knew the team would have to be put up for sale, Ricketts said.

When I spoke with Sal Galatioto in August of 2016 he provided tremendous insight into why he decided to work with the Ricketts family as opposed to the countless other groups who tried to retain his services as they tried to buy the Cubs. The Ricketts are so well organized and they really think things through. They plan everything before they make a decision and they take the long-term view as opposed to so many others who take a short-term approach.

GSP is perhaps the best company in the United States in the sports acquisitions industry and while the competition to purchase the Cubs was going to be tough, Ricketts also faced competition to convince Galatioto that he and his family were the right people to own the Cubs. Tom made it clear to me from day one that the family was all Cubs fans and that they didn’t want to buy just any professional baseball team. They wanted to own the Chicago Cubs and that was very important to me. I wanted to represent someone who really had a passion for the team they were buying. They were obviously wealthy and that combined with the reputation of the family and their love for the Cubs were huge factors in working together to help them acquire the franchise, Galatioto said.

I didn’t think that Tom was crazy when he approached me about buying the Cubs, but at that point the Tribune Co. was telling everyone who inquired that the team wasn’t for sale. Throughout all of my years in this business I’ve come to realize that things that look nuts today aren’t nuts tomorrow. The Cubs are one of the most iconic franchises in all of sports and they are more of a national brand rather than a local brand as so many other teams are. Teams like the Cubs don’t usually come on the market, Galatioto said.

But as the Ricketts and GSP continued to meet and to strategize as they pursued the Cubs, rumors started to run rampant that the iconic franchise was indeed going up for sale. Tom Ricketts’ intuition had been right on the money years earlier.

"Tom was very astute and his knowledge of the financial picture of the Tribune Company gave him and his family a head start on the process of pursuing the Cubs if they were to hit the market. The team was owned by a large corporation and large corporations, more than individuals, sometimes they decide for whatever reason they are going to sell assets.

I knew if a team like the Cubs came on the market there was going to be a lot of competition. It’s not like you’re trying to sell a team in Podunk. It’s Chicago, which is a great market, and it’s the Cubs, which is a great brand, and so you have a lot of investors who want to buy the team, Galatioto said.

However, having money and loving a team as a fan is far from enough to get into the club of billionaire owners of professional baseball teams. It is quite possibly the most exclusive club in the world and no matter how wealthy a prospective owner is, Major League Baseball and the other 29 owners have to be comfortable with who they are admitting to their club or the deal will never get the required approval.

"Tom knew nobody in Major League Baseball so we had to introduce him to the important guys in baseball so that they would get comfortable with him. I called Jerry Reinsdorf and he was so gracious to the Ricketts family. He had Tom and his siblings and dad up to his skybox for a White Sox game and he cleared the box so we could all have a very honest and frank discussion.

We spent three hours talking philosophy and the baseball business. Jerry wanted to know why they wanted to buy a team and why they wanted to buy the Cubs. And the family showed really, really well. Jerry really liked them and he felt that they would be great owners. They understood that owning a baseball team was a marathon not a sprint. Having Jerry in their corner was really important because owning a team is like trying to get into a really exclusive country club. You have to have someone of great stature in the game who feels comfortable with you and is willing to stand up in a meeting and say, ‘These are good people and they will be good for our sport,’ Galatioto said.

Having Reinsdorf in their corner was important, but the Ricketts family needed more than just Reinsdorf if they were going to win the bidding for the Cubs and gain approval from the hierarchy of Major League Baseball. They had to meet several of the most influential people in the sport so they could be a group that the baseball insiders who run the sport would be comfortable approving, if and when the Ricketts could come to terms with the Tribune Company to buy the franchise.

We went around the game meeting different key owners so they would get comfortable with Tom, Galatioto said. "We met with Bob DuPuy, who was the deputy commissioner of Major League Baseball, so he and his family really became a known entity throughout the upper levels of Major League Baseball.

Also, you have to remember that when the Cubs came on the market it was at a very dark time in American economic history. The world was falling apart. The banks weren’t lending and the Tribune Company had issues and people thought it would be difficult to raise money. You name it, it was going on. It was a mess. It took a long time to get this deal done—plus, the Tribune was difficult to deal with, Galatioto said.

Then, if you remember the Tribune filed for bankruptcy in the middle of the sale process and so we had to navigate that. The Cubs were part of that bankruptcy and while it was a prepackaged bankruptcy we still had to navigate that. Major League Baseball didn’t want that stigma but we all understood that it had to be done. We had to distance ourselves from all the other junk that was falling around in the Tribune system, Galatioto added.

The Ricketts family was one of a handful of groups that