A look at John W. Henry’s incredible sports empire

John W. Henry made the decision to begin building a sports empire after acquiring a fortune through his trading firm in the 1980s. Indeed, instead of retiring, Henry began looking at the prospect of purchasing some of the most recognizable global sporting brands in the world. It was then, in 2002, when Henry bought the Boston Red Sox for $380 million, which effectively started his journey as one of the most successful owners of any era.

At the time, the Red Sox hadn’t won a World Series in 86 years and had largely been making up the numbers in the MLS after treading water for decades. That was to change, however, when the Sox broke their drought by winning the 2004 edition of the World Series, just two years after Henry had begun overseeing operations. It was indeed a case of mission accomplished for Henry but he didn’t take his foot off the accelerator and instead, delivered three more World Series titles in 2007, 2013, and 2018

Essentially, Henry has been able to not only break the World Series curse over the club that stretched back to 1918 but also deliver four titles in just two decades. It’s also worth pointing out that despite being 72 years old, Henry is still a hands-on owner who is intent on winning another World Series title. But it may not be this season, with the MLB odds pricing the Red Sox at a speculative +4000 to make it five trophies since 2002. Still, you wouldn’t write them off just yet.

Whatever happens, Henry may still claim more silverware this season but this time with Liverpool Football Club, a global institution that Fenway Sports Group bought back in 2010.

Again, Henry got involved with Liverpool at a time when the Reds’ best days were seemingly behind them after the club last won the league in 1990. Before that, Liverpool were the dominant team in English soccer and no one could have predicted that they would enter the trophyless wilderness for so long. It did take Henry ten years, but he was finally able to deliver Liverpool the Premier League title in 2020, three decades after the Reds had last hoisted aloft the greatest prize in English soccer.

During this time, Henry has also overseen two League Cup triumphs as well as a stirring Champions League final victory in 2019. It would also be remiss to fail to mention that Jurgen Klopp’s team have appeared in three Champions League finals in the last five years. Similarly, Liverpool have finished runners-up to Pep Guardiola’s Manchester City on two occasions over the last four seasons. Put another way, Henry has come agonizingly close to rewriting the history books but has, to a certain extent, been undone by fate.

That won’t take away from the fact that Henry has given Liverpool and indeed the Boston Red Sox some of their best days over the course of their illustrious history. 

Once described as the greatest investor in the US, Henry is a visionary who has changed professional baseball and soccer for good.

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