Liverpool owner John W Henry reaches another summit

When John W. Henry sat down in his new office in Fenway Park in 2002 for the first time since he and his ownership group acquired the Boston Red Sox for $660 million, the challenge ahead of the then 53-year-old businessman and founder of the John W. Henry & Company management firm was more than clear.

Expel almost a century’s worth of bitter disappointment and bring a World Series title to a city that hadn’t celebrated one since 1918. It’s not that the Red Sox didn’t have any success in that gaping time frame; Boston won the American League Pennant four times since their last championship parade in 1946, 1967, 1975 and 1986.

But each time the Red Sox came a step away from enshrinement in baseball lore, a Bill Buckner moment would happen. Boston was cursed, and the 26 World Series arch-rivals New York Yankees had won throughout their history only served as a constant, reverberating reminder.

After a rather ineffective three-year stint as owner of the then-Florida Marlins — whom he sold after failing to secure an agreement to build a new stadium — in came Henry, whose resume was full of accomplishments but who was far from a sure thing as an owner of a professional sports franchise. But following the purchase, Henry quickly assembled a top-tier organisation that would give Red Sox fans a dash of hope.

In 2004, Boston at last won a championship, and perhaps the biggest reason is that Henry put his faith in a 28-year-old Yale graduate. Theo Epstein has reached legend-status nowadays, as he assembled not just one but two World Series winners in Boston as the youngest general manager in MLB history, and then preceded to bring the Chicago Cubs a World Series in 2016 — another broken curse, as they hadn’t won one since 1908 — as their President of Baseball Operations.

Henry may not be the man who scouted and trusted in David Ortiz or assembled a pitching staff led by Pedro Martinez and Curt Schilling, but he took a floundering organisation and blossomed it into a winning one.

Henry’s ownership of the Boston Red Sox continues to this day, but wasn’t satisfied with the three World Series (2004, 2007, 2013) his franchise has won. In 2010, the Fenway Sports Group — Henry’s and partner Tom Werner’s company (previously named New England Sports Ventures) that owns the Red Sox, part of the New England Sports Network, Fenway Park, Fenway Sports Management and numerous real estate properties in Boston — expanded its breadth across the pond.

John W Henry and Ian Ayre look onward

As Liverpool F.C. are set to square off against Real Madrid on Saturday at 19:45 in Ukraine in the UEFA Champions League Final, it’s pertinent to take a look back and contemplate on the path the Reds have taken since the club changed ownership nearly eight years ago.

Following an exhaustive legal battle that resulted in the wrestling away of Liverpool from the hands of former-owner and American private equity investor Tom Hicks, in October of 2010 Henry had acquired another team adorned in red. Though Liverpool do not have the near-century long voyage of sorrow the Red Sox did, the decade before Henry’s takeover had not lived up to the prestigious weight that Liverpool’s name carries.

Liverpool established themselves as stalwarts in the late 20st century, when the club was led by names like Bill Shankly, Bob Paisley, Joe Fagan and Kenny Dalglish to 11 titles from 1972 to 1989. It was the golden age for fans of the mighty Reds, but those times much feel further and further away with each passing year and each failure to attain the elusive Premier League title.

In the 25-season existence of the Premier League, Liverpool have failed to win even one title and have been the runner-up just twice. They’ve taken other trophies like the Champions League in 2005 and the FA Cup a year later, but the year-in-year-out dominance of the past was just that — in the past.

Thus, another challenge for John Henry. Bring a club famed for former glory back to the top of the throne where they belong. Henry’s CV with the Red Sox is more than encouraging, but Liverpool fans would quickly learn their new owner isn’t immune to tumultuous times.

John W Henry and Jurgen Klopp on the pitch at Anfield

After breaking Boston’s curse in 2004, the Henry-owned Red Sox also won in 2007 and 2013,  but the years dotted between were murky. In each of the four years after its second Henry-era championship, Boston won at least 89 games, but in 2012 they plummeted to 69 wins. That was the one and only season for Bobby Valentine as skipper, who was canned that October.

Boston bounced back and won another World Series the next season under new-manager John Farrell, but the two years after, they were right back in the basement, finishing last in the American League East in 2014 and 2015 and winning less than 80 games in each season. This was in large part because so much of the Red Sox’s payroll was invested in disastrous free agents contracts given to ageing duds like Carl Crawford and Pablo Sandoval.

The Red Sox have since settled in as a consistent contender — albeit with another new manager, Alex Cora — winning their division the past two years and sitting in first place now, but the turbulence seen in the franchise was in a way mirrored in Henry’s early ownership of Liverpool.

In 2012, Henry made headlines by firing manager Kenny Dalglish, a somewhat surprising move given Dalglish’s success with the club in the late 1980s. Henry followed up with another manager firing three years later when he sacked Brendan Rodgers, who had taken Liverpool to a runner-up finish in the Premier League two seasons prior.

John Henry is tantalising yet harrowing. An owner to have pride and confidence in, but also one that reminds you to always be aware of the storm that’s just around the corner.

The Henry-era Reds won the League Cup in 2012, but they have a chance to take the next step towards supreme greatness in the Champions League final against Real Madrid. Sometimes it’s easy to forget because of how much Liverpool have depended on Mohamed Salah this season, but from Henry’s perspective it’s an event that has been years in the making.