Winning in Both Leagues: Reflections from Baseball’s Front Office by J. Frank Cashen (review)

Frank Cashen wore many hats—advertising executive, newspaperman, lawyer, racetrack publicity director, baseball executive—finally, memoir author. In Winning in Both Leagues, Cashen (who died in June 2014 at eighty-eight years old) tells the improbable story that landed him as the architect for two World Series-winning franchises.

Cashen’s autobiography is the latest offering from the New York Mets World Series-winning club of 1986. Dwight Gooden, Darryl Strawberry, Mookie Wilson, and the late Gary Carter have all recently detailed their experience with one of baseball’s more colorful and successful teams. Cashen’s perspective, however, offers valuable variance given his management status.

The strength of Cashen’s story is that his voice is maintained throughout. The turns of phrase, for example, give readers the feeling that Cashen himself is in the room, spinning the yarns. Ultimately, every good autobiography strives for that level of intimacy and authenticity and Winning in Both Leagues succeeds there.

Given the length of his career working for the Baltimore Orioles, Major League Baseball, and the Mets, Cashen met a lot of noteworthy personalities and provides anecdotes that keep the reader’s interest. Cashen, a noted “mover-and-shaker,” orchestrated many trades over the course of his career. From a fan standpoint, there is an insatiable knowledge about the behind-the-scenes structuring and negotiations of player deals. Cashen, for the most part, capably illuminates to outsiders the inner workings of some of his more memorable swaps (Gary Carter) or near-trades (Rusty Staub).

Winning in Both Leagues, however, falls short on several fronts in part because it seems incomplete and sanitized. Cashen frequently appears to be playing it safe in retelling his story. The Mets, for example, were a team plagued with players troubled with substance-abuse problems, but at no point does Cashen convey management’s concerns with the off-field issues of some of its star talent. When the Mets acquired Keith Hernandez from the St. Louis Cardinals, the deal was largely the Cardinals off-loading a player believed to have cocaine issues and represented part of a larger purge of these “problem” players from the Cardinals roster. Cashen retells his trade discussions with Cardinals general manager Joe McDonald regarding Hernandez, but at no point does the author mention whether Hernandez’s cocaine use came up. It surely did.

In this vein, Cashen also steers clear of singling out people he did not like in the industry. Aside from George Steinbrenner, whose demise preceded Cashen’s, the author’s disagreements with anyone related to professional baseball seem surprisingly few. In a game of egos and competition where the stakes have always been high, either Cashen was the most affable man to earn a living in the sport, or he was not forthcoming with his squabbles. The reviewer can understand his reluctance to rehash old beefs, but the truth is the best autobiographies are painfully honest. Perhaps the vanilla character to Winning in Both Leagues is a testament to Cashen’s gentlemanly nature, but it leaves readers feeling they are not getting the whole story. Winning in Both Leagues is not a long book, so certainly Cashen had room to include these details, dirty as they might be.

Beyond the curious omissions, the structure of Winning in Both Leagues leaves something to be desired. Unnecessary flipping back and forth destroys any attempt at momentum. It is not uncommon to encounter a four-page chapter, which is fine if the book is read on a commuter train, but the result is a choppiness that has a negative impact on flow.

On balance, Winning in Both Leagues is disappointing. No one disputes that Frank Cashen has a valuable story to tell. This reviewer merely hoped he would do so with more depth and a willingness to address turmoil along his prolific path.