Award-Winning Leadership Speaker, Executive Coach & New York Times Best-Selling Author

Have Don Yaeger speak to your team!

5 Things We Can Learn From the Downfall of the Boston Red Sox

My grade school teachers severely undersold the lessons on compound words.

While “downfall” fits the grammatical parameters of a compound word, its definition in the business world is complex mostly because it is most often the result of a series of compounded mistakes.

I often look to sports for lessons that can be useful across many spectrums and the recent downfall of the Boston Red Sox baseball franchise, while painful to some, is a homerun in lessons to be learned. The team that won two World Series Championships in the past eight seasons has quickly turned into a cautionary tale on leadership and as baseball prepares for this year’s World Series, it is important to take notes from these classic failures. In fact, here are 5 things we can learn from the 2012 Boston Red Sox debacle:

  1. Think Long-term: Boston is undeniably one of the most history-rich franchises in Major League baseball. That kind of staying power doesn’t develop from nearsighted decisions. Forward-thinking is what put former Red Sox manager Terry Francona into a winning spotlight. His philosophies helped add championship shine to an organization that had long labored in the shadows of the New York Yankees pinstripes. But two championship rings weren’t enough to keep Francona as the long-term option. The thirst for immediate results led management to sign players to inflated contracts, chilling team chemistry. After a September meltdown one year ago, the Red Sox found themselves drowning in a sea of offseason questions… They blamed the manager and later hoped to make a sudden splash by hiring a recognizable character in Bobby Valentine. Evident by the two-year contract he was offered, ownership clearly saw Valentine as a short-term fix full of uncertainty.
  2. Trust those you hire: Adopting a short-term business model, Boston increased the payroll and put the highly visible Valentine in charge of it. But the flare of one of the sport’s most coveted job opportunities came with strings attached. The organization refused to let Valentine hire his own assistant coaches. By limiting his ability to hire his own staff, the franchise muzzled his authority before he even had the chance to put on the uniform. Limiting his leadership led to … a lack of leadership. This one is on ownership.
  3. Know Your Personnel: The franchise leadership overlooked the various personalities already in the clubhouse when they brought in a polarizing soul like Valentine. Everyone knew Valentine was not afraid to speak his mind, which is why he was so good as a broadcaster on ESPN. In similar fashion, Valentine didn’t take the time to learn his clubhouse egos and quickly lost the respect of veteran players. The overwhelming disconnect between Valentine, his leadership team and his team leaders quickly lead to a breakup.
  4. Internalize the Issues: Rather than address team concerns within the organization, Valentine chose to go public with his criticism. Complaints this past April about Boston veteran and beloved All-Star third baseman Kevin Youkilis quickly turned into a costly error. In fact, it sparked responses from within the clubhouse by fellow all-stars and so much discontent that the Boston brass had to step in. Wanting to show confidence in their initial hire of Valentine, the franchise backed their limited leader and traded Youkilis. The move didn’t settle any of the tension and eventually a disastrous (69-93) season meant Boston would begin searching for its third manager in as many years.
  5. Cut Your Losses: While it may have been done in extreme hindsight, the franchise did cut its losses after a season of too many. At some point, pride has to be put aside for the overall benefit of the team. In a late season trade with the Los Angeles Dodgers, the franchise dumped almost a quarter of a billion dollars in player contracts from their books. Gone now are nine standout and handsomely paid members of the 2011 team (Josh Beckett, Carl Crawford, Adrian Gonzalez, Jed Lowrie, Jonathan Papelbon, Josh Reddick, Marco Scutaro, Jason Varitek, and Kevin Youkilis), two managers (Francona and Valentine) and one general manager (Theo Epstein). By reducing their payroll and stocking up on young talent, it appears the Red Sox might finally be getting back to the kind of forward thinking that put them into the World Series conversation over the last decade.

Businesses worldwide spend countless hours and enormous portions of their operating costs protecting themselves against the dreaded downfall.

Chances are had specific items on this list been handled differently, the BoSox likely would still be competing in the playoffs instead of completely rebranding and rebuilding. Hopefully the franchise will take these lessons into account as they approach this next leadership team…and this next season.

What signs as a leader are you currently ignoring? Can you identify any lessons from the Red Sox downfall?

Join the conversation today.

Tags: , , , , , , , , , , , , , , , , , , ,

Connect with Don Yaeger  

Where would you like to start the conversation?



413 N. Meridian St.
Tallahassee, FL 32301

 (850) 412-0300

Follow Don Yaeger


Certified Speaking Professional (CSP)

About Don Yaeger

Don Yaeger

Don Yaeger is a Certified Speaking Professional (CSP), longtime Associate Editor for Sports Illustrated, 11-time New York Times best-selling author, leadership expert and executive coach.

 Read Full Bio here

    Your Cart
    Your cart is emptyReturn to Shop


    Don Yaeger

    Don Yaeger is ready to speak with you

    Connect With Don
    Anjie Cheatham – Director of Marketing and Events

    Anjie Cheatham
    Director of Live & Virtual Events

    Connect with Don's team directly by calling (850) 412-0300 (8:30AM – 6:00PM EST)

     Send Email