Baseball fans—and anyone who likes a good comeback story—will really enjoy Knuckleball, a new documentary that explores this confounding pitch through the eyes (and fingernails) of the two most recent players to throw it: Tim Wakefield, who retired from the Boston Red Sox after last season; and R.A. Dickey, who is having a Cy Young-caliber year for the New York Mets.

The movie makes clear that adopting the knuckleball is almost always a desperate move of last resort—both Wakefield and Dickey were on the verge of having their careers cut short before being saved by learning to throw this pitch. Dickey’s career, in fact, almost ended before it started—and therein is the insurance connection.

He was drafted in the first round in 1996 by the Texas Rangers and originally offered an $825,000 contract. But after a routine examination, it was discovered that his pitching elbow is missing its ulnar collateral ligament—doctors were amazed he could even turn a doorknob without pain let alone fire a fastball. As a result, the Rangers dropped the offer to a measly $75,000.

Turns out that as a sophomore in college, Dickey had taken out a $1 million insurance policy on his right arm—and so, at 21, he faced a momentous decision: cash in the policy—which would have then barred him for life from playing professionally ever again—or pursue his passion.

Dickey chose to pitch and obviously the gamble paid off handsomely. His salary this year? $4.75 million.

There is one horrible part to the movie—it forced this Red Sox fan to watch again and again (in slo-mo and even backwards), Wakefield’s homerun pitch to Aaron Boone in Game 7 of the 2003 ALCS against the Yankees (a game I had the great misfortune to be at, watching it with KBW’s chief insurance analyst and fellow sox fan, Cliff Gallant).

Special Reports /

R.A. Dickey, Cy Young Contending Pitcher, Opted Not to Cash In on $1 Million Insurance Policy

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