We're two summers away from the end of the Bob Iger era at Walt Disney (NYSE:DIS), and this time it doesn't seem as if it's a head fake. Disney's CEO is insisting this week that he plans to stick to his plan to leave the media giant once his contract ends on July 2, 2019. Iger's contract has been extended three times, the last being earlier this year.

"This time I really mean it," he said at the time of his springtime extension. He essentially repeated those words on Tuesday afternoon when he presented at Vanity Fair's New Establishment Summit. 

Iger will be 68 at that point, but he doesn't seem to have any interest in riding off into the sunset of a cozy and well-earned retirement. Hollywood Reporter, Vanity Fair, and CNBC have all reported in recent months that Iger associates have been nudging him to consider running for president in 2020. There's no shortage of celebrities and business executives that have publicly pondered the possibility of vying for the highest political office in three years, but let's turn our attention back to the roost that Iger is presently ruling. What if Disney doesn't have a clear replacement for Iger by the summer of 2019? What if there are too many transitions and transformations taking place within the multi-dimensional entertainment behemoth itself to make any handoff at the helm risky? What if Disney still needs Iger? 

Bob Iger and James Cameron at the Grand Opening of Pandora -- The World of Avatar.

Bob Iger at the grand opening of Pandora-The World of Avatar that debuted at Disney's Animal Kingdom in May. Image source: Disney.

To infinity and beyond

There's no denying the game-changing impact that Iger has had at Disney. The board tapped him -- then the company's COO -- as Michael Eisner's replacement on March 13, 2005. The stock has gone on to more than quadruple during his dozen years at the top. 

Iger has proven to be a master negotiator. Eisner departed as friction escalated with Pixar. Iger arranged an outright buyout. Iger would go on to negotiate deals for Marvel and Lucasfilm in the years that followed. The Pixar, Marvel, and Lucasfilm acquisitions were all 10-figure transactions, but the successful franchises acquired make all three deals great ones in retrospect. 

Finding a replacement for Iger won't be easy. Then COO Tom Staggs seemed to be his heir apparent, but he left the company early last year. Disney's board won't rush to name a replacement until we get closer to Iger's departure date, but it's going to be the source of speculation and perhaps unwelcome uncertainty in the coming quarters.

The thorniest thing about Iger's exit strategy is the timing. If he does leave in 22 months it will be with a lot of things up in the air. 

  • The over-the-top Disney streaming service will have rolled out earlier in 2019, giving it a shot to escape the decaying state of linear television. Iger will be leaving before we have a chance to know if it's gaining traction. 
  • The ninth and final installment in the Star Wars franchise will hit theaters in 2019, placing a lot of weight on potential spin-offs that are unlikely to be as lucrative as Lucasfilm's crowning achievement.
  • Star Wars Land will open at Disneyland and Disney World in 2019, a key component in the massive makeover taking place at its domestic theme parks.

In short, Iger will be leaving at a time when a lot of big things have to go just right. We're also assuming that Disney's recent financial shortcomings will be remedied by then, something that may not be the case if the struggles at ESPN, sluggish theme park attendance, and multiplex industry woes continue. There may never be a good time for Iger to hang up his mouse ears, but 2019 may be a particularly awful time to risk fumbling a handoff.  

Rick Munarriz owns shares of Walt Disney. The Motley Fool owns shares of and recommends Walt Disney. The Motley Fool has a disclosure policy.