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Steve Swindal almost owned the Yankees, but things went badly wrong

“Owning the New York Yankees is like owning the Mona Lisa,” George Steinbrenner once said, comparing his Major League Baseball team to the masterpiece of Leonardo da Vinci. Indeed, in the myopic world of sporting fixation, there are few more lucrative possessions than that fabled ballclub in the Bronx.

According to Forbes, the Yankees are worth $5 billion, a figure so otherworldly that only 330 humans currently inhabiting planet earth could afford to buy the team outright without the support of external investors. That is 0.00000423% of the global population. Even George Lucas does not have the cash to purchase the Bronx Bombers, and he created the Evil Empire. We are talking serious money here. Serious money.

In many ways, then, the Yankees are akin to the British royal family with regard to ownership and authority. They operate a monarchy with a line of succession to the throne that is notoriously difficult to infiltrate. Outsiders are rarely welcomed, while births and deaths are greeted with the pomp and circumstance of a secular island nation.

This elusive, impenetrable and invincible powerbase adds to the Yankees’ legendary mystique. Yes, the team has won 27 World Series championships, more than double any other organisation, but its commercial success off the field is arguably even more impressive. The Yankees have one of the most recognisable brands in the world, and the associated gravitas adds to a compelling aura. There is just something so fascinating about the pinstriped conglomerate. It inspires awe around the globe.

“The majority of American males put themselves to sleep by striking out the batting order of the New York Yankees,” famed cartoonist James Thurber once said. Meanwhile, the majority of American businessmen put themselves to sleep by counting the Yankees’ cash register, visualising a fantasy nirvana where they own the most illustrious sports team ever created.

In modernity, one man came closer than any mere mortal not named Steinbrenner to realising that dream, only to blow it in harrowing fashion. Steve Swindal, a one-time furniture wholesaler from Tampa, Florida, married into one of the most powerful families in America and worked his way through the ranks. However, just when he seemed set to inherit the family business, seizing control of the New York Yankees, disaster struck. It is difficult not to rank Swindal’s epochal meltdown among the biggest fuck-ups of all-time.

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How George Steinbrenner bought the Yankees and became the most powerful owner in sports

A bombastic shipping magnate, George M Steinbrenner III bought the Yankees from Columbia Broadcasting System (CBS) for $8.8 million in January 1973. The purchase price may have risen to $12 million, according to some media reports, but today, the team is still worth almost 600 times what Steinbrenner paid for it. There has never been a greater investment in sports history.

After amassing great personal wealth as a serial shipbuilder, Steinbrenner initially wanted to buy the Cleveland Indians, a forlorn franchise close to his hometown of Bay Village, Ohio. A handshake agreement was even struck with Jimmy Stouffer, the Indians’ incumbent owner, only for unfavourable leaks in the press to curtail a potential deal. Steinbrenner then turned his attention to the Yankees.

After a decade of stagnation under the corporate purview of CBS, the Yankees needed a facelift in the early-1970s. Upon taking over, Steinbrenner vowed to be an absentee owner, promising not to interfere with daily operations. That changed almost immediately, however, when the advent of free agency made it possible for the Yankees to bid on the most talented players in baseball. 

Steinbrenner’s innate desire to win overwhelmed the team’s traditional structure, and he soon became the most meddlesome managing partner in baseball history. The Yankees signed big ticket free agents like Catfish Hunter, Reggie Jackson and Dave Winfield, offering unprecedented salaries to turbocharge a tentative rebuild. The Bombers won three straight pennants between 1976 and 1978, hauling in two world championships in the process. George liked what he saw, and he was determined to replicate the success.

“Winning is the most important thing in my life, after breathing,” Steinbrenner once said. “Breathing first, winning next.” To that end, the Yankees were held to rigorously high standards by their owner, ominously dubbed The Boss by one and all. Famed New York cartoonist Bill Gallo even referred to the Yankees’ owner as General von Steingrabber, depicting him as a Prussian general bedecked in military uniform and a comic spiked helmet. Tabloid ridicule be damned, George was determined to build an empire. In the end, that is exactly what he did. Baseball has never been the same since.

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Who is Steve Swindal, and what is he famous for?

For any twenty-something guy, meeting the parents of a potential lover for the first time is a daunting proposition. You likely remember the feeling – nervy, antsy, clammy even. Well, just put yourself in the shoes of Steve Swindal for a second here, and you will be thankful for your own lukewarm experiences.

In the late-1970s, a mutual friend in Tampa introduced Swindal to Jennifer Steinbrenner, the daughter of George and a fellow University of North Carolina alum. Steve and Jennifer began dating, then they became a couple. One day, Swindal had to face the ultimate imposing father-in-law. Imagine telling The Boss you were sleeping with his daughter. Now that is pressure, dear readers. That takes some balls.

Ultimately, however, George liked Swindal from the outset. The Boss admired Steve’s work ethic, which helped make a success of the Swindal family business: selling furniture from a warehouse. Born in 1955, a proud Floridian, Steve actually wanted to become a doctor but was not accepted into medical school. He later earned a history degree from UNC, graduating in 1976, before returning to his humble roots in Tampa.

Of course, parts of the Yankee operation were headquartered in Tampa, Steinbrenner’s adopted citadel. The family lived in luxury, a far cry from Swindal’s blue collar milieu. Nevertheless, Steve and Jennifer married in 1983, and Swindal bonded with George through mutual passion for sports, history and boats. In a world where everybody wanted something from him, Steinbrenner respected Swindal’s contented nonchalance. The guy who did not ask for anything was set to inherit it all.

At first, Swindal continued selling furniture even after marrying into the Steinbrenner dynasty. However, he eventually went to work for George at the American Shipping Company, a driving force of the family’s wealth. Swindal also ran a small tugboat enterprise for Steinbrenner, who was able to sell it for a handsome profit in 1995. That opened George’s eyes to the potential of Jennifer’s husband. That made Swindal a candidate for greater power.

George and Joan Steinbrenner had four children – Hank, Jessica, Jennifer and Hal – but succession planning for ownership of the Yankees was a troublesome topic for many years. The Boss instantly dismissed the notion of his wife or daughters taking control, while Hank and Hal struggled to meet their father’s exacting standards of ambition and comportment. George struggled to manufacture intimate bonds with his progeny, and the concept of selecting an eventual successor at Yankee Stadium caused him great turmoil from his earliest days of ownership.

In many ways, George grew closer to Steve than he ever did to Hank or Hal. Sure, the sons of Steinbrenner roamed the Yankees’ clubhouse and were groomed for roles in the organisation one day, but The Boss saw natural leadership qualities in Swindal, whose understated passion spoke of a bright future.

A huge fan of history, Steinbrenner’s greatest hero was legendary field commander General Patton, and he prized the kind of steely determination Swindal had in spades. An interesting - if slightly awkward - dynamic soon opened up in the Steinbrenner household, where the son-in-law commanded more respect than anybody other than George.

In 1997, The Boss offered Swindal the chance to become a general partner of the Yankees, taking a leading role in the front office. Once an everyday outsider, Swindal became chairman of Yankee Global Enterprises, achieving the ultimate fantasy of testosterone-fuelled dudes in frat houses across the land by infiltrating a sporting superpower. Steinbrenner gave him a small stake in the Yankees, enhancing the surreal daydream. Tampa Steve could not believe his luck.

Despite success on the field, George yearned for a new ballpark to future-proof the Yankees’ empire. When New York City officials were less than cooperative in negotiations, Steinbrenner discussed selling 70% of the franchise to Charles Dolan of Cablevision for $365 million in 1998. At one stage, a deal seemed to have been agreed, but George reneged at the last possible moment, consolidating his autonomy. “I do not intend to ever get out of the Yankees,” said Steinbrenner. “I do not intend to ever let the Yankees go.”

With that, attention turned to the future, and George became obsessed with succession planning. Aged 70 in 2000, Steinbrenner had a morbid preoccupation with his own legacy, and he was particularly keen to minimise the burden of inheritance tax on his family.

A convoluted selection process rumbled on in George’s chaotic mind, akin to the college of cardinals selecting a new pope in the Vatican. Eventually, sacred white smoke billowed from Yankee Stadium, cast against the gothic frieze. A new Yankee owner was anointed in principle, and nobody was more shocked than the heir apparent himself.

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Why George Steinbrenner selected Steve Swindal as heir to the New York Yankees

Conscious of external scrutiny and the sharp sword of nepotism, Steve Swindal worked exceedingly hard for the Yankees. A shrewd operator, he helped launch the YES Network, which greased the wheels of Yankee domination. Swindal also played a key role in transforming the political discourse around building a new stadium for the ballclub in New York. Where George was a bulwark, thoroughly obtuse and rough around the edges, Swindal was a conduit, open to diplomacy while still packing a ruthless punch. The Yankees needed such a nuanced approach, and it drove the organisation towards new frontiers. 

Swindal grew close to general manager Brian Cashman and famed skipper Joe Torre, extending his power. The Yankees won four World Series titles in five years between 1996 and 2000, with Swindal playing an increasingly important role. Nevertheless, when New York lost to Florida in the 2003 World Series and to Boston in a crushing 2004 American League Championship Series, an institutional crisis brewed on River Avenue, and Swindal was often forced to play peacemaker between warring internal factions.

A fight for the Yankees’ soul encompassed several key powerbrokers. Steinbrenner receded into ill health, lacking the consistency of yore and lurching from one extreme stance to another. Hal and Hank meandered around without codified job descriptions. Cashman battled with a deep state branch of executives in Tampa, trying to wrest control of baseball operations. Randy Levine controlled the team’s commercial philosophy, with Lonn Trost chiming in for good measure. Meanwhile, Torre bickered with everyone and anyone in the dugout, grumpy at his lack of job security.

As for Steve Swindal? Well, he was the lynchpin holding this whirling maelstrom of dysfunction together. He was the avatar of future progress. Yankees fans praised his influence on message boards and forums of the time, whereas Hal in particular was chastised for not being tough enough.

Indeed, Swindal often sat next to George at Yankee Stadium, becoming a chief sounding board for big decisions as The Boss approached the twilight of his premiership. A reliable filter for George’s bluster, Swindal became a key confidant at a tumultuous time in pinstriped history. Steinbrenner appreciated such support, and his mind was made up with regard to succession plans.

To that end, in June 2005, Steinbrenner announced that Swindal would replace him one day as managing partner of the Yankees. In typically bombastic style, George dropped the bombshell during a press conference relating to an entirely different topic - the team’s plans to break ground on its new ballpark. According to later retellings, even Swindal was shocked at the news. Still, George pressed ahead with his contrarian vision.

“Yes, Steve will be my successor,” said Steinbrenner through Howard Rubenstein, the Yankees’ spin doctor, when pressed for confirmation after the explosive media briefing. “I also have other sons, daughters, sons-in-law and daughters-in-law coming along and they will remain involved. As I have said many times, ‘you must let the young elephants into the tent.’”

However, one of those young elephants came from outside the original herd. Steve Swindal rose from nowhere to become the heir apparent to baseball’s most sacrosanct dynasty. Following George’s earlier metaphor, it was like being gifted the Mona Lisa for Christmas by your father-in-law. While everybody else got socks or cologne, Swindal got the New York Yankees. He continued to win the lottery of life, one remarkable step at a time. 

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How Steve Swindal rose to power within the Yankees

Reading between the lines, Swindal had something of a power trip after being tabbed to replace George. Years later, Torre published his memoir, The Yankee Years, in collaboration with Tom Verducci, and it includes several fly-on-the-wall anecdotes that depict Swindal’s management style in unflattering shades. There was obvious friction between the manager and his would-be boss, but it can be difficult to make any tangible deductions from Torre’s final years in office, as he became quick to hold grudges.

Nevertheless, in one 2006 incident, The Yankee Years recounts Swindal blowing up at Torre and Cashman following a 19-1 loss to the Indians on the Fourth of July. “I pay you and Joe all this money!,” Swindal purportedly yelled while enjoying the holiday on a luxury boat. Some felt that Swindal tried too hard to imitate his father-in-law, and the fallout was not always pretty.

The Yankees bombed out of the playoffs in 2006, just as they did in 2005 and 2004. Once unstoppable, the pinstriped juggernaut turned stale – on the field, at least, even if commercial revenues continued to surge. As the new stadium rose like a phoenix across the street, thoughts turned to new horizons and uncertain futures. Swindal was the face of that future, as much a part of the team’s long-term vision as Derek Jeter or Alex Rodriguez. In many ways, Swindal was even more powerful than those mere ballplayers, for he had George’s ear, and soon he would have his keys.

Accordingly, when Swindal shared a podium with Major League Baseball commissioner Bud Selig and New York City mayor Michael Bloomberg in February 2007, he was on top of the world. The trio announced that, in 2008, Yankee Stadium would host the All-Star Game in its final season before demolition. Swindal fronted the press call amid an ever-expanding remit. “We’re excited,” he said, speaking for the organisation. “It just seemed appropriate.”

Indeed, that Midsummer Classic proved to be an absorbing spectacle, as Yankee dignitaries were serenaded one last time on baseball’s main stage. Steve Swindal was not among the procession, however, and he would never again reach such a spine-tingling zenith. You see, exactly two weeks after the All-Star Game announcement, Swindal’s universe imploded in the most scandalous way imaginable. Thirteen years later, we are still analysing the wreckage.

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How a DUI arrest and subsequent divorce stopped Steve Swindal becoming Yankees owner

“Steve Swindal was the man who would be king of one of the most valuable properties in professional sports,” wrote Verducci and Torre in The Yankee Years. “[However], Swindal’s authority was soon to be wiped out by one of the most expensive drinking benders in the history of imbibing.” 

Shortly after 04:30 am on 15th February 2007, cast in the shifting gloom of Valentine’s Day just gone, Swindal was arrested by St Petersburg police after driving erratically through the night. The Yankees’ heir failed a sobriety test and refused to be breathalysed. He was booked for driving under the influence of alcohol (DUI), and within hours his mugshot was splashed all over the internet, bringing the pinstriped institution into disrepute.

After drinking heavily throughout a tempestuous evening with Jennifer, Swindal climbed into his brand new Mercedes and planned to drive to his boat, docked nearby, to sleep off the tension. Speeding at 61-mph through a 35-mph zone, Swindal weaved in and out of traffic before cutting off a police cruiser at a neighbourhood intersection. The mother of all hangovers accompanied a night in jail and the loss of America’s most emotive sporting jewel. Steve was throwing it all away.

A week after the arrest, Swindal said he felt embarrassed but hoped to remain part of the Yankees organisation. In turn, the Yankees apologised for Swindal’s actions and set about evaluating his position within the franchise. However, his expulsion became a foregone conclusion when Jennifer filed for divorce, citing ‘irreconcilable differences,’ barely a month after the DUI charge.

“Steve and Jenny Swindal announced today that they are amicably ending their marriage of 23 years,” said Rubenstein in a family statement. “Although their marriage is dissolving, they remain friends and maintain a strong mutual respect. They are devoted to their two children and will make them their shared focus.”

With that, Steve Swindal – the guy who lived our workaday dream by coming within touching distance of owning the New York Yankees – was excommunicated from the family business. Internally, George pondered ways of working things out, hoping to keep his most valued executive, but even The Boss was resigned to the impossibility of such a concept.

In September 2007, Steinbrenner forced through a $5 million buyout of Swindal’s ballclub stake. A few weeks later, Swindal pleaded no contest, agreeing to the suspension of his driver’s licence for six months, a year of probation and 50 hours of community service. His magic carpet ride was most assuredly over. 

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The human cost of Steve Swindal's demise

With Swindal removed from the line of succession, a disgraced divorcee who lost it all, Hank Steinbrenner became the presumptive Yankee heir. However, in an unforeseen twist, George eventually settled on Hal as the spearhead of his baseball estate. Hal replaced Swindal as the chairman of Yankee Global Enterprises, and on 20th November 2008, the owners of Major League Baseball ratified Hal as the team’s new managing partner.

In painstaking theory, Swindal only had to keep clean for 645 days and he would have been in control of a $5 billion company. Even the Mona Lisa is worth only $850 million, and besides, French law says the painting can never be sold. Therefore, the next time you have a bad day, just remember that a guy once came that close to owning the Yankees only to see it all implode. No matter how bad your morning is, it is unlikely to include a DUI scuppering the inheritance of sports’ most sacred possession.

In 2009, whispers appeared in the notorious Page Six gossip columns of the New York Post stating that Swindal was attempting to get back in the Yankees’ good graces. Some say he attempted to patch things up with Jennifer, but a full reconciliation never quite materialised.

Still, by all accounts, the pair maintained a cordial relationship, and when George died of a heart attack at the age of 80 in July 2010, Swindal joined the family as it dedicated a plaque to The Boss in Monument Park. Since then, though, Swindal has rarely returned to the new Yankee Stadium, a $2.3 billion amphitheatre he helped conceive. 

To that end, a melancholy pathos bathes this tragic story. Though archived court documents say otherwise, pointing to a staggered relationship breakdown, one has to wonder whether the split of Steve and Jennifer was a divorce of baseball convenience more than it was a heartfelt necessity. Certainly, I wonder if Jennifer felt pressure to conform to unfair ideals in this regard, crushing the love of her life simply because he embarrassed the New York Yankees.

If that is the case, we as fans must shoulder some of the blame here. When all is said and done, baseball is just a game, and the Yankees are just a team. Sure, they mean a lot to us, and they come to represent an ineffable purpose in our hearts, but to think that public involvement with a sports franchise expedited the decline of an otherwise sturdy marriage is somewhat traumatic. It traverses murky turf between passion and stupidity.

Indeed, for the longest time, Steve Swindal has been discarded as a footnote in baseball history. He has been written off as the guy who stood to inherit a fortune but could not help himself, pissing it all up the wall. To a certain extent, that is an accurate portrayal, but we must acknowledge the implications of such a seismic event in one’s personal life, not least from a mental health perspective. I hope that Swindal has been able to find peace, because rarely has any human been more plagued by what if? premonitions than him.

Certainly, it is difficult to find a direct parallel to Swindal’s demise in the annals of popular history. There are similarities to the plight of Ronald Wayne, a co-founder of Apple who lasted just 12 days at the company before selling his 10% stake to Steve Jobs and Steve Wozniak for $800 in 1976. Wayne’s equity would be worth $94 billion today.

Likewise, Swindal can surely relate to the demons of James Monaghan, who in 1961 traded half of the humble pizza store he co-owned with his brother in return for a second-hand Volkswagen Beetle. That humble pizza store became Domino’s, a company that now has yearly revenues of $3.6 billion.

In sports, one of the few comparisons to Swindal being jilted at the altar of Yankee opulence can be found in Los Angeles, where Jeanie Buss once fired her brother Jim as head of basketball operations for the Lakers. Even that story lacks the unheralded underdog sentiment of Swindal’s rise, however. Here was a guy who married into fame, came awfully close to fortune, and ultimately went up in flames. There is not much company in that exclusive club.

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What are the odds of any human owning the New York Yankees one day?

If you will excuse a little napkin mathematics at this point, I would like to estimate the sheer improbability of Swindal’s ascension. Please bear with me on this – I appreciate the logical leaps that are required. This is still fun for illustrative purposes, nevertheless. Take it all with a pinch of salt. 

Excluding familial bequeathing, ownership of the New York Yankees has changed hands just six times since the ballclub was formed in 1901. For 30 years, Jacob Ruppert and his estate controlled the team. For a further 47 years, Steinbrenner and his clan have presided at the Stadium. Accordingly, 64% of the Yankees’ existence has been spent in patriarchal ownership, leaving just a window of 36% for outsiders to make a purchase.

In those 119 years of Yankee operation, 12.1 billion people were born on planet earth. If we take that 36% figure – otherwise seen as the ballclub’s availability for ownership outside family lineage – we can reduce that population to 4.3 billion potential franchise buyers in history.

If we then take today’s global rate of individuals who can afford to buy the Yankees outright - 0.00000423% - and apply it to the aforementioned 4.3 billion potential historic suitors, we are left with 184 people who could possibly have purchased the team at any point in the last 119 years.

In theory, then, any single human being to have lived in the past 119 years had – or has - a one in 65.7 million chance of someday owning the New York Yankees. For context, that hypothetical person is more likely to be struck by lightning 93 times than to mass the requisite individual wealth at just the right time to purchase baseball’s most lucrative team. They are also more likely to be attacked by a shark on five separate occasions; to hit 5,400 holes-in-one on the golf course; and to die in a plane crash than to call the shots at Yankee Stadium.

A pretty big deal, huh? Well, that is what Steve Swindal gave up when he climbed behind the wheel drunk. That is what Steve Swindal sacrificed when he slalomed through the night. That is what Steve Swindal lost, on top of his famous marriage. I struggle to compute the magnitude of that mistake. It will never cease to amaze me.

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Where is Steve Swindal now, and who will be the next Yankees owner?

By 2009, Swindal worked his way back into baseball, launching a player academy in the Dominican Republic that helps amateurs earn contracts with major league organisations in the US. Profiled by CBS New York in 2012, Swindal said a few things added to his Yankees departure, not just the DUI, but to everybody else, it has always seemed pretty clear cut.

“It’s a strange turn,” said Swindal in the exclusive article. “Life is going to be full of turns and changes. It’s how you deal with it that’s important. I had the best ten years of my life with the Yankees, of my professional life. I don’t regret a minute of it.”

Indeed, Swindal is still a wealthy, successful executive whose resume includes more than a decade inside the New York Yankees' nerve centre. Swindal remains an influential figure within the boating community of Tampa Bay. He was eventually reappointed chairman of the Tampa Bay Port Authority, in addition to overseeing a shipping assistance venture. In 2015, Swindal bought a huge condo overlooking Central Park for $1.4 million, so pause your tears for his supposed demise.

Ironically, the son of Steve and Jennifer - Steve Swindal Jr. - still works for the Yankees in baseball operations, and he has voiced interest in taking over as managing partner one day. There are several candidates for the next generation of pinstriped ownership, and the selection process promises to be equally contentious moving forward, but the underdog is rooting for Steve’s son, if only for the soap opera symmetry.

“This is a family business and we are all involved,” Hal Steinbrenner told ESPN in 2017. “We all love being a part of this. We all know our dad wanted us to be a part of this, and we all know he is watching down on us and happy that we are all a part of it. Believe it or not, to us, that is a big deal. The idea is: let’s keep it going.”

Sadly, Hank Steinbrenner died in April 2020, aged 63. Amid the commemorations, many industry experts whispered about the line of succession, noting how a crop of bright young executives rests on the horizon. Now 50 years old himself, Hal acknowledged that the Yankees are already engaged in those talks, and that several of George’s grandchildren have expressed an interest in running the Yankees one day.

There are 14 grandchildren in total, but three spring to mind when contemplating future owners - Robert Molloy, the son of Jessica Steinbrenner, who works in the Yankees’ media team; the aforementioned Steve Swindal Jr., who recently got a start in baseball operations; and George M Steinbrenner IV, the son of Hank, who in 2018 became the youngest IndyCar team owner of all-time aged just 22.

Personally, I would love to see George Steinbrenner – in name, if not in stature – back in the big chair at Yankee Stadium somewhere down the line. It just seems so poetic. Nevertheless, a huge part of me wants Steve Swindal Jr. to make that leap and redeem his father’s legacy. If nothing else, that would make for some interesting discussions around the dining table. It would also provide some closure to an open wound that will never go away.

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Steve Swindal did not respond to requests to be interviewed for this story.

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Ryan Ferguson is the author of Conflict: The Yankees, the Red Sox and the War for My Heart, available now in paperback and Kindle formats through Amazon. Click the link below to get your copy now!

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