Brian Cashman, Dodgers bat boy

Brian Cashman is synonymous with the New York Yankees. Hired as an intern in 1986, promoted to assistant general manager in 1992, and handed the keys to baseball operations in 1998, the polarising figurehead seems permanently ensconced in the Bronx. (1)

Cashman has five World Series rings encrusted with the interlocking NY, burnishing revered credentials, but a 15-year championship drought has cast doubt on his effectiveness. No matter how vociferously Yankee fans call for his ouster, though, Cashman enjoys ironclad job security. An honorary member of the Steinbrenner family, many say he has the role for life, hegemony approaching a fourth decade.

Before all that, however, Brian Cashman hated the Yankees. Before the drought and the toxicity, The Boss and the internship, Cashman grew up a Dodgers fan – an act of rebellion against his Yankee-loving family. The fact that Brian was born in New York, and that he grew up in Lexington, Kentucky, did not matter. He loved the Dodgers, and even wrote letters to the team, informing officials they had a rabid fan back east. (2) (3) 

In 1977 and 1978, when Cashman was 10 and 11, the Dodgers lost successive World Series to the Yankees, and the little guy was devastated. “I thought I’d never see a Dodger world championship,” he said years later, traumatised by Reggie Jackson’s storied metamorphosis into Mr October. That Jackson would one day advise Cashman, chief Yankee architect, strained the bounds of credulity. But that is exactly what transpired. (2)

Firstly, though, Cashman rooted for the Brooklyn transplants, and that championship he doubted arrived in 1981, when the Dodgers finally beat the Yankees in a World Series riven with volcanic meltdowns by George Steinbrenner, the pinstriped emperor. The Boss fought with two mouthy Dodger fans in a hotel elevator during the Fall Classic, then issued a formal apology to the people of New York when the Yankees lost in six games. (4) (5)

The Cashman family was accustomed to the Steinbrennian doctrine of success at all costs. John Cashman, Brian’s father, was a legendary horse racing executive who had The Boss as a client. In fact, whenever John sold George a horse that did not win, Steinbrenner fumed and withheld payments. Meanwhile, John Cashman III, Brian’s brother, trained George’s horses, preceding his sibling as a Steinbrenner employee. (3)

Brian also worked with horses in his formative years, but baseball was always his greatest passion. Brian fell in love with the Dodgers of Ron Cey and Steve Garvey, and that interest was nurtured by former Brooklyn pitcher Ralph Branca, who became friendly with John Cashman while attending horse races at Pompano Park. (6) 

A three-time All-Star, Branca entered baseball infamy by surrendering Bobby Thomson’s Shot Heard ‘Round the World homer against the Giants in a 1951 National League tiebreaker. Young Brian picked Branca’s brain, and the pair often discussed baseball. So much so, when Brian visited his grandmother in Florida during spring training of 1982, Branca leveraged his contacts to score the teenager a dream day at Dodgertown in Vero Beach. (7)

After meeting Garvey, his favourite player, and posing for a photograph, Cashman was given a full road grey Dodger uniform and the opportunity to run errands for the big league team. Tommy Lasorda, the team’s iconic manager, also posed for a picture with Brian, later signed for his parents with the following message: “You, the Dodgers, and Brian are all great.” (3)

Evidently enamoured, Lasorda offered Brian the chance to serve as the Dodgers’ bat boy in a spring training game – which he did. Lasorda was a hard taskmaster, though. “He would yell at me, ‘Don’t let that bat hit the ground,’” Cashman told the New York Times in 2024. “‘You get out there and get that bat before it hits the ground. I want to see you sprint.’” Lasorda later took credit for giving Cashman his start in baseball – a tongue-in-cheek charade befitting his avuncular schtick. (2) (3)

Truth be told, however, Steinbrenner gave Cashman his real start in the game – as a 19-year-old intern in 1986. A Division III ballplayer for Catholic University, Brian was in Florida during a road-trip when he lost his travel money in a card game. John Cashman told Brian to visit Allen Finkelson, the Pompano publicist, and ask for a small loan to tide him over. (3) 

Brian did just that, and discovered a shrine of Yankee memorabilia in Finkelson’s office. The inquisitive Cashman asked about the Yankee World Series ring on Finkelson’s finger, and the PR guru said Steinbrenner was his best friend. The pair continued to chat, and after learning of Cashman’s travel ball plans, Finkelson posed a question that – unwittingly – changed the course of baseball history: “What if I can get you an internship with the New York Yankees?” (3) (8)

Cashman jumped at the opportunity – despite his nascent Dodger lust and the recurring nightmares of Reggie’s famous homer disappearing into the Yankee Stadium abyss. And so Finkelson spoke to George and landed Cashman a role beginning that summer.

Brian assisted the minor league scouting department during the day and worked stadium security – yes, stadium security – at night. Prior sentiment dissipated with such exposure to baseball’s inner sanctum, and new motivations – the desire to progress, the will to win, the nurturing of professional pride – took over when Cashman first walked through those monolithic doors. From day one, he was totally committed to the Yankees, and climbing the slippery ladder became his chief obsession. (7)

From stapling minor league scouting reports and escorting drunks from the bleachers, Cashman progressed rapidly. After graduating with a history degree in 1989, Cashman became a full-time baseball operations assistant with the Yankees. A year later, he was promoted to assistant farm director, before crossing to major league administration in 1991. General manager Gene Michael made Cashman his assistant in 1992, and Bob Watson, Michael’s successor, kept him in that role en route to winning the 1996 World Series. When Watson resigned before the 1998 season, Cashman was recommended for the top job, and Steinbrenner acquiesced. (9)

The Yankees won five pennants and three world championships in Cashman’s first six years as GM – all before the wunderkind turned 40. And despite an epochal ALCS implosion against the Red Sox in 2004, Cashman remained one of the most coveted executives in sports.

As such, when his contract expired following the 2005 season, Cashman at least explored other options. Poetically, those options included the Dodgers, who sought a new baseball operations head after firing Paul DePodesta. Frank McCourt, the Dodgers’ owner, pursued Cashman heavily, and initial talks yielded a hypothetical marketing campaign with a clever – if cheesy – premise: The Bat Boy Returns. McCourt offered to double Cashman’s salary and awaited a decision. (2)

At that point, alert to the possibility of losing his protégé, Steinbrenner asked Cashman to stay with the Yankees – a rare concession from the tempestuous patriarch. Out of loyalty to Steinbrenner, who believed in him as a neophyte, Cashman agreed to stay – landing a pay rise, greater autonomy, and a remit to modernise the Yankee front office. Rejected by their boyhood fan, the Dodgers turned to Ned Colletti. (2)

Cashman led the Yankees to another world championship in 2009, while the Dodgers plummeted towards bankruptcy, but baseball’s two pre-eminent powerhouses zigzagged in the 2010s – Los Angeles, under the fresh ownership of Guggenheim Baseball Management, morphing into a paragon juggernaut, while New York, under the stale aegis of Cashman, embarked on the second-longest title drought in franchise history.

After winning a Covid-besmirched title in 2020, the Dodgers rubber-stamped their ascent to supremacy by beating Cashman’s Yankees in the 2024 World Series – a true changing of the guard among baseball’s titanic teams.

In power for 27 years, and without a title for the last 15 of those, Brian Cashman has – by contrast – outstayed his welcome, according to many Yankee fans. The Dodgers, meanwhile, have dynastic desires, and everyone wants to imitate them.

In that regard, maybe their bat boy could save the Yankees one day, with history repeating itself.

His name is Javier Herrera, for what it is worth. 

Perhaps he is destined for pinstripes.

Sources

1. Golenbock, Peter. George: The Poor Little Rich Boy Who Built the Yankee Empire. 2010.

2. Waldstein, David. New York Times. [Online] October 28, 2024. https://www.nytimes.com/2024/10/28/nyregion/brian-cashman-yankees-dodgers.html#:~:text=The%20Dodgers%20beat%20the%20Yankees,and%20he%20set%20it%20up.

3. O'Connor, Ian. ESPN. [Online] September 25, 2019. https://www.espn.com/mlb/story/_/id/27684222/how-survive-22-years-yankees-gm-brian-cashman-thank-hall-fame-father.

4. UPI. [Online] October 26, 1981. https://www.upi.com/Archives/1981/10/26/New-York-Yankees-owner-George-Steinbrenner-suffered-a-possible/5562372920400/.

5. Gross, Jane. New York Times. [Online] October 29, 1981. https://www.nytimes.com/1981/10/29/sports/steinbrenner-issues-an-apology-to-fans.html.

6. Dodger Talk podcast. [Online] October 24, 2024. https://www.iheart.com/podcast/519-dodger-talk-28250979/episode/dodger-talk-10-24-24-231078094/.

7. Araton, Harvey. New York Times. [Online] March 19, 2011. https://www.nytimes.com/2011/03/20/sports/baseball/20cashman.html.

8. Martino, Andy. The Yankee Way: The Untold Inside Story of the Brian Cashman Era. 2024.

9. Wikipedia. [Online] https://en.wikipedia.org/wiki/Brian_Cashman.