Sports ownership
Henry grew up a fan of the St. Louis Cardinals, especially their star Stan Musial. After acquiring his fortune, his first foray into professional sports was in purchasing a Minor League Baseball team, the Tucson Toros of the Pacific Coast League, in 1989. He was also one of the founders of the Senior Professional Baseball Association, a winter league in Florida composed of retired major league players.
Henry co-owned the winning team in the 1989–90 season, the West Palm Beach Tropics, managed by Dick Williams, former manager of the Boston Red Sox's 1967 team, known as the "Impossible Dream" team.
In 1990, Henry sold his interest in the team, and the league went out of business the following year. The same year, he negotiated to purchase the Orlando Magic, a National Basketball Association team. He also was briefly the lead general for the Colorado Rockies, a Major League Baseball expansion team, and headed a group attempting to acquire the National Hockey League's expansion team in Florida, which was ultimately awarded to Phil and Tony Esposito, who created the Tampa Bay Lightning. Henry subsequently negotiated to buy the Miami Heat and later the New Jersey Nets.
Henry entered Major League Baseball with his purchase of a small interest in the New York Yankees in 1991. Henry became the sole owner of the Florida Marlins in 1999, purchasing the club from Wayne Huizenga for a reported $158 million. In January 2002, Henry sold the Marlins in a multi-franchise deal to Jeffrey Loria, then owner of the Montreal Expos, which is now the Washington Nationals.
In 2001, Henry partnered with Tom Werner, The New York Times Company, and other investors to found New England Sports Ventures (NESV) in a successful bid to buy the Boston Red Sox from Yawkey Trust headed by John Harrington. Henry became principal owner of the Red Sox, with Werner as chairman.
The company has since become majority owner of English Premier League club Liverpool F.C., the Pittsburgh Penguins, the New England Sports Network, Fenway Park, Fenway Sports Management, and other assets.
In 2009, the company made its first foray into European sports with an unsuccessful bid for the French Ligue 1 club Olympique de Marseille.
NESV changed its name to Fenway Sports Group in March 2011.
Henry canceled the previous owners' plans to demolish Fenway Park and build a new stadium next door. Instead, Henry renovated Fenway—among other things, adding seats over the Green Monster—enabling the park to celebrate its centennial in 2012.
Henry and Werner assembled a front-office team headed by Larry Lucchino with the goal of "breaking the Curse of the Bambino." He also hired baseball sabermetrics pioneer Bill James, whose work became widely known after the 2003 publication of Moneyball. Henry accomplished his goal in the 2004 World Series, defeating his former childhood favorite Cardinals. The team won the 2007 World Series against a franchise with which Henry had pre-expansion involvement, the Rockies, and the 2018 World Series against the Dodgers. The Sox beat the Cardinals again in the 2013 World Series.
In August 2017, Henry said the team would lead a campaign to change the name of Yawkey Way, a section of Boston where Fenway Park is located. The Red Sox had been the last team in Major League Baseball to integrate, and Henry said, "I am still haunted by what went on here a long time before we arrived." The change was approved by the City of Boston in April 2018, and the name reverted to Jersey Street in May 2018.
In October 2010 the Fenway Sports Group took over Liverpool F.C. The UEFA Financial Fair Play Regulations may have been a factor in the decision. The previous owners, Tom Hicks and George N. Gillett, Jr., had become extremely unpopular among Liverpool fans for their failure to deliver on the promise that no debt would be placed onto the club, and the proposal of Liverpool leaving Anfield as disrespectful treatment of its manager and front office and for their allegedly misleading statements about planned and past investment in players.
After losing around £154 million on the pressured sale of their debt-ridden club, Hicks and Gillett announced that they would sue co-owners and creditors for at least $1.6 billion for the "extraordinary swindle" they suffered. In January 2013, Hicks and Gillett had lost a Court of Appeal case and agreed to drop the suit.
On February 26, 2012, Liverpool won the 2012 Football League Cup Final at Wembley Stadium, beating Cardiff City 3–2 on penalties after the game finished 1–1 after 90 minutes and 2–2 after extra time. This was Liverpool's first trophy since the 2006 FA Cup Final win over West Ham United on May 13, 2006, at the Millennium Stadium in Cardiff. In May 2012 he made a controversial decision by firing coach and club icon Kenny Dalglish citing the club's poor league results. This was regarded as a poor decision by some soccer pundits such as Dalglish's friend Alan Hansen, given Dalglish's success in lifting the club from four points above the relegation zone to a cup win. In July 2012, after persuading Brendan Rodgers to become the new coach, Henry attributed parting company with Dalglish as being unrelated to failing to win the FA Cup or the Suarez case, but a product of the club's poor league performance in the second half of the 2011–12 season.
Rodgers almost took Liverpool to their first Premier League title in over 20 years during the 2013–14 season; however, poor performances in the subsequent season and a bad start to the 2015–16 season saw Henry sack Brendan Rodgers as Liverpool coach on October 4, 2015. On October 8, 2015, Henry appointed Jürgen Klopp as the new coach of Liverpool F.C. The move was praised by Liverpool supporters and seen as a show of Henry's ambition for the club. Klopp led Liverpool to two finals during the 2015–16 season (the League Cup and the Europa League). In 2018 Liverpool reached the Champions League final for the first time in 11 years. In 2019 Liverpool reached the Champions League Final for the second consecutive year and won it, beating fellow English club Tottenham Hotspur, 2–0. Liverpool went on to win the Premier League title in the 2019–20 season; Liverpool's first league title in 30 years, and their first since the Premier League was formed.
In April 2021, Liverpool were announced as a founding member of the European Super League, which would have effectively ended the pyramid system of European soccer and placed Liverpool in a closed league without prospects for meritocratic relegation and promotion. Liverpool and the five other English clubs involved backed out within two days after a strong backlash. This prompted Henry to issue an official apology to Liverpool fans, taking responsibility for the events that had occurred.
In 2007, Henry's Fenway Sports Group bought a 50% stake in Jack Roush's Roush Racing stock car racing team. Driver Matt Kenseth won the Auto Club 500 at the California Speedway in February 2007 marking Henry's first win as an owner. In February 2009 the team won their first Daytona 500 with Matt Kenseth. Henry is currently listed as the owner of the #17 Ford driven by NASCAR Cup Series driver Chris Buescher.
In September 2004 Henry and David Kaemmer founded iRacing.com Motorsport Simulations for developing a racing simulation service aimed at both real-world racers and racing simulator enthusiasts. The service was launched in August 2008.
