How Brian Cashman turned mud into gold during the Yankees' rebuild

I finally understand, respect and appreciate Brian Cashman. For so long a frustrating enigma, the Yankees general manager has illustrated his adroit efficiency in recent years, rebuilding the Bronx Bombers amid a shrewd blueprint devised by Hal Steinbrenner.

While the Yankees have not won a World Series title since 2009, Cashman has never enjoyed more power, and nor has he ever built such a sustainable juggernaut. In this complicated age of baseball quantification, he may just be the best executive currently in charge of a major league organisation.

Why Brian Cashman is the most underrated executive in sports

Brian Cashman is a visionary. Behind all the bluster, there was a reason why George Steinbrenner hired him in 1986. Sure, The Boss was friends with Cashman’s father, but Brian belonged to the new breed of baseball nerd that rose to dominance amid the Moneyball revolution. All v-neck sweaters and sandy coloured chinos, Cashman viewed the game differently. He foresaw the changing landscape and tried with all his might to steer the Yankees clear of trouble.

Originally a baseball operations intern, Cashman grew close to Gene Michael, who seized day-to-day control of the Yankees when Steinbrenner was suspended in 1990. Under Michael’s aegis, Cashman soared through the Yankee organisation, becoming an assistant farm director and a trusted confidant for key power-brokers. He eventually became general manager in 1998.

Many of Brian’s contemporaries from that age of Sabermetric awakening are lavished with praise. Theo Epstein is a media darling. Billy Beane is a Hollywood fascination. Andrew Friedman has been deified. Heck, even Peter Brand, a fictional number cruncher, has been afforded more praise than the man who helped deliver five world championships to the Yankees in thirteen years. Brian Cashman has quietly outperformed everyone, and finally his skill is being appreciated.

For a generation, when considering baseball’s brightest minds, Cashman was perpetually overlooked due to the depth of his budget and the aggression of George’s overarching philosophy. The Yankees spent more on player payroll than many small countries can muster for vital provisions such as health and education. Therefore, mainstream baseball fans deduced that he was somehow inferior to those operating within much stricter parameters.

Brian Cashman was branded an average puppet devoid of true autonomy; an underwhelming academic who fell into the greatest job in sports merely through good timing and old-fashioned nepotism. Anybody could win 100 games with $350 million to spend on salaries – or so the argument went. The Yankees’ cost-per-win ratio was routinely higher than that of any other team, and many analysts viewed that as a measure of Cashman’s mediocrity.

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Behind the scenes, the Yankees’ general manager knew that, to a certain extent, those naysayers were correct. He felt confident in his ability to win the same amount of games, and perhaps even more, while spending considerably less money.

A data-driven moderniser, Cashman fought with George regularly, attempting to articulate the complex changes that were required to compete in the revenue-sharing era of prospect envy and luxury taxes. Addicted to the heroin of superstar flirtation, Steinbrenner fuelled fractures within the Yankees’ front office, maintaining a cohort in the Tampa office that undermined Cashman’s power base.

For those reasons, among many others, Cashman was never able to implement his full vision of cost-effective competition. Winning today was always more important than planning for tomorrow, and fielding a championship calibre team on Opening Day every year fell within Cashman’s job description.

As the major league environment changed, achieving that vacuous goal became increasingly difficult, to a point where the Yankees were satisfying nobody. By 2008, they lurked as a giant shadow of their former selves, caught between a rock and a hard place, shorn of an underpinning ethos conducive with latter day success.

Fortunately for Cashman, Hal Steinbrenner shared his vision for a sharper, slicker and more sustainable Yankee enterprise. Hal and Brian were cut from the same cloth, preferring objective analysis to subjective conjecture. That made their choice of occupation somewhat oxymoronic, but in a strange twist of destiny, their strategy was fit for glory in the contemporary age. 

Hal Steinbrenner and Brian Cashman - the unlikely duo leading the Yankees' analytics revolution

Hal succeeded his father in 2008, taking control of the Yankees as a reluctant chairman. A sharp-witted hotelier, Hal enjoyed baseball, but his brother Hank received George’s burning passion for the game. Hal derived pleasure from longwinded strategy and cutting-edge ideation rather than from knee-jerk gratification. When thrust into the most powerful seat in sports, he did not deviate from that analytical approach, preaching the need for a new culture on River Avenue.

Hal Steinbrenner dedicated many years to learning about baseball markets and sporting success. He did not have a natural flair for the game, but he put in plenty of hard yards to prepare for the ascension. Cashman’s voice was never the loudest – that is not his style – but Hal was taken aback by the passion, intelligence and ingenuity of his general manager. When Cashman suggested something, Hal typically agreed. The two guys worked on logic.

Between 2009 and 2015, the Yankees took a hybrid approach to rebuilding, gradually refining their assets and pruning their resources while vaguely honouring George’s mandate to compete without caveats. A further world championship was delivered in 2009, but later attempts to replicate the model proved unsuccessful. The Yankees missed the playoffs in 2013 and 2014, while 2015 ended in wildcard defeat to Houston. It was just not working anymore, and Cashman lobbied for a total teardown. He was tired of suggesting. He wanted to act.

Wearied by annual luxury tax bills that fuelled the success of less committed teams, Steinbrenner agreed to the revolutionary plan. In the winter of 2015, he gave Cashman greater power than he had ever wielded before - under one condition: that the Yankees try everything in their power to build a long-term winner without incurring huge salary penalties.

How Brian Cashman rebuilt the Yankees between 2015 and 2018

With consolidated authority and a new objective – to get better, younger and cheaper – Cashman decimated Major League Baseball. In the space of 24 months from December 2015, the Yankees dismantled their devolving nucleus and built a new core.

In December 2015, Cashman traded Adam Warren and Brendan Ryan to Epstein’s Cubs in return for Starlin Castro. A year later, Castro was flipped to Miami along with Jose Devers and Jorge Guzman - two prospects accumulated in a November 2016 trade of veteran catcher Brian McCann to Houston – for Giancarlo Stanton, the best damn power hitter in the world.

Elsewhere, before the 2016 season, Cashman acquired Aroldis Chapman from Cincinnati for mediocre prospects named Eric Jagielo, Caleb Cotham, Rookie Davis and Tony Renda. Midway through a faltering campaign, Chapman was dealt to the Cubs for a package including uber prospect Gleyber Torres and middling youngsters Rashad Crawford and Billy McKinney. Adam Warren also returned in the deal, while the Yankees re-signed Chapman to a five-year, $86 million free agent contract after he won a ring in Chicago.

That financial commitment was offset by the retirements of Alex Rodriguez and Mark Teixeira in 2016. Carlos Beltran, another ageing journeyman, was also traded away, as the Yankees got leaner. Likewise, bullpen ace Andrew Miller netted four great prospects from Cleveland, headlined by Clint Frazier.

Essentially, in a two year-period, Brian Cashman completed the following equation:

With eight transactions, Cashman subtracted 13 players and added 14 new ones. Among that respective sample, between 2016 and 2017, Cashman increased the team’s seasonal wins above replacement (WAR) total by 77% while cutting payroll in half. The group also got four years younger on average.

Extrapolated to the wider roster, the Yankees won 84 games with a $213 million payroll in 2016. Following Cashman’s resuscitation project, Fangraphs projects that New York will win 93 games in 2018 while spending just $168 million. That would constitute a 10% increase in wins and a 21% decrease in expenditure. Not to mention the replenished farm system brimming with elite talent on the cusp of major league readiness.

In other words, those ancient yarns of Yankee inefficiency can be retired, because the game has rarely seen a more dominant two-year stretch by any general manager in its history. I have been critical of Brian Cashman. I have been immensely frustrated by the real-time disappointments of his long-term strategic approach. However, the bigger picture is now clear for me to see, and the New York Yankees could not be in safer hands.

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