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From Lovable Losers to Lovable Leaders

For many, Cubs fever is still upon us. No matter which baseball team you root for (unless it’s Cleveland) there’s a part of you that is surely excited that the Lovable Losers from Chicago’s North Side have finally ended the longest title-less streak (by a long distance) in professional sports, a whopping 108 years. As a New Yorker-in-exile (and avid Yankees fan) living in the Windy City for a dozen years, I got to observe what it was like to be a Cubs fan up close. And believe me, it was not pretty.

I was there when Steve Bartman interfered with Moises Alou along the left field foul line in 2003. I observed the National League leading Cubs get swept in the first round in 2008. And of course I heard all about the curse of the Billy Goat, the black cat, and all of the other reasons as to why a North Side champion was a near-impossibility. 

Refrains like “better luck next year” (in April, mind you) and “everyone can have bad century” remain well etched in my mind. As someone who grew up rooting for George Steinbrenner’s Yankees (love him or hate him) the notion that mediocrity was acceptable, let alone embraced, went against my very nature.

But something changed over the past few years. The Yankees former nemesis, Red Sox championship architect Theo Epstein, took the reins at Wrigley and began to build a winner. With some existing assets (acquired through some early futility) and deft maneuvering, Epstein has turned the Cubs into what appears to be a perennial powerhouse with strong nucleus of young talent.  

As I admire the turnaround from a distance, it strikes me that there are a number of lessons that all organizations and / or their leaders can learn from Epstein and his team, particularly struggling entities that are experiencing a need for change of direction. These include…

1.       Find a winning architect with turnaround success – As noted above, Epstein’s history of turning around a BoSox squad that had not tasted a championship since the Curse of the Bambino must have appealed greatly to Cubs’ brass. While there was no guarantee of similar results in Chicago, at least it gave everyone involved hope. The same is true with any organization requiring a turnaround. When a leader possesses a history of success, it instills confidence and helps rally the troops. That person is not part of the losing past and can see a situation for what it is, not for the history and baggage that it carries. Any organization that can move forward with such a leader will often see that “can’t do” attitude shift into something much more positive and promising.

2.       Stay patient – It’s easy for impatience to set in when you have over a century of misery all around you (the Cubs are easily the first franchise to 1000 losses). Great leaders, however, develop a blueprint to success and make every effort to see it through. They believe in their plan and find ways to get others to understand and believe in it as well. 

3.       Build from ground up – Epstein tore up what he found and began anew, building around a core group of young players (akin to the Yankees’ “Core Four” of the late 1990’s). These players could appreciate the team’s history but were too young and disconnected from the suffering to be burdened by it. More importantly, these players (many of who were top draft selections) were very talented, and had the ability to produce concrete results on the field.

4.       Bring in proven field-level winners – Epstein helped his cause by bringing to Chicago a bunch of people who had tasted winning previously and could bring that attitude to the clubhouse. He began with the manager. Joe Maddon had taken another perennial doormat (Tampa) to the 2011 World Series and knew a thing or two about breaking with tradition and developing young talent. He also added a few seasoned vets (Lester, Zobrist, Heyward et al) with winning experience. Good leaders know that it helps to augment the leadership ranks and the clubhouse with skilled personnel who have been through change before and have experienced success. Such people can help leadership implement its vision by not only adding their talents to the mix but also through assuring holdovers of better days ahead.

5.       Going for the kill – One of the hardest moves Epstein had to make was to part with some of his finest young talent to acquire the services of hard-throwing Yankees closer Aroldis Chapman. He did it because he saw Chapman as the missing piece to the championship puzzle (which proved correct, particularly in the World Series). Getting Chapman also added even more confidence to a roster that was growing quite accustomed to raising the W with regularity a year after making it to the NLCS. This move said, “I believe in you and gave you every tool to succeed. Now go get it.” Great leaders understand when they have reached the tipping point, the moment when they need not look over their shoulders but can focus squarely on the future. Then they find ways to strengthen the group that they’ve built even further and give them every opportunity to succeed.

Turning around any organization or company with a checkered past can challenge even the most successful leaders. Using some of Epstein’s tactics can help make the process simpler and may even produce the kind of winner that can exorcise every demon in the building.

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