The Big Picture
Following the news that former Liverpool co-owner George Gillett has died at age 87 after a battle with Alzheimer's Disease, sports fans are re-examining one of the most turbulent ownership spells in modern football history. From his early days in American sports and ski resorts to his high-stakes takeover at Anfield, Gillett lived at the center of major sports business headlines. Here is the definitive ranking of the top ten moments that defined his sporting legacy.
Building the Empire: Early Moves and Hockey Success
10. Entering American Entertainment with the Harlem Globetrotters
Gillett expanded his portfolio beyond traditional team sports by acquiring a stake in the iconic Harlem Globetrotters. While it was a secondary venture compared to European football or the NHL, it signaled his commercial ambitions across North American entertainment.
This entry ranks at number ten because it showcased his preference for heritage sports brands long before he ever stepped foot on Merseyside. It demonstrated an early pattern of investing in recognized cultural assets with established fan bases.
9. Securing an Ownership Stake in the Miami Dolphins
Gillett secured a minority share in the NFL franchise, placing himself inside one of America's premier sports leagues. The Dolphins venture provided him with valuable exposure to stadium economics and high-stakes media rights negotiations in South Florida.
It ranks ninth because while financially lucrative, it lacked the direct executive authority he would later exercise in Canada and England. His limited stake meant he was an investor rather than the driving force behind front-office decisions.
8. Building a Financial Base Through Ski Resorts
Long before acquiring premier sports teams, Gillett built his primary wealth through North American ski resort operations. That early commercial success generated the liquid capital required to purchase world-famous sporting institutions in the 2000s.
It sits in the eighth spot as the indispensable economic engine that made his later high-profile sports ventures possible. Without the cash flow from these resort properties, his entry into elite professional sports ownership never occurs.
7. Buying the Montreal Canadiens in 2001
Gillett crossed into Canadian sports by purchasing the Montreal Canadiens, controlling the storied franchise from 2001 to 2009. He successfully modernized the business operations of the NHL original six team while earning respect across Quebec.
This ranks seventh because it established his credibility as a hands-on sports proprietor prior to his Premier League move. His period in Montreal proved he could successfully manage a traditional sports franchise with deep civic roots.
6. Hosting the Canadiens Centennial Celebration
During his time in Quebec, Gillett led the organizational preparations for the Canadiens Centennial Celebration, honoring a century of hockey history. NHL commissioner Gary Bettman noted how Gillett guided the team through that milestone while respecting the franchise's rich legacy.
It takes sixth place because it represented the absolute high-water mark of his popularity as a sports team owner. Unlike his subsequent tenure at Anfield, his stewardship in Montreal earned genuine praise from league executives and local supporters.
“George Gillett’s passion for the Montreal Canadiens and commitment to the city of Montreal were demonstrated throughout his tenure as owner of the storied franchise from 2001 to 2009.” — Gary Bettman
The Anfield Era: Takeover, Turf Wars, and Turmoil
5. Clashing Publicly with Manager Rafael Benitez
Gillett and Tom Hicks repeatedly clashed with manager Rafael Benitez over transfer budgets, squad recruitment, and overall club direction. The public friction eroded supporter trust and undermined stability on the pitch during a pivotal window for Liverpool.
This moment lands at fifth because it exposed the deep operational fracture inside Anfield's executive suite to the entire football world. Rather than supporting a manager who had reached two Champions League finals, the co-owners engaged in public political battles.
4. The £174 Million Takeover of Liverpool FC in March 2007
In March 2007, Gillett partnered with fellow American businessman Tom Hicks to complete a takeover worth £174m to buy Liverpool FC. As Mirror Football reported, the purchase promised new stadium construction and major financial backing for the Premier League giants.
It ranks fourth because it fundamentally altered the economic trajectory and governance of Liverpool Football Club. The debt-funded nature of the buy-out immediately placed heavy financial strain on the club's operating budget.
3. Escalating Fan Protests and Internal Co-Owner Fallout
As debt mounted on the club, Liverpool supporters launched organized protests against Gillett and Hicks outside Anfield. The two American business partners eventually stopped speaking directly to each other, creating a destructive administrative deadlock.
This breakdown ranks third because it pushed one of world football's most storied institutions to the brink of financial disaster. The toxic dynamic between the co-owners turned Anfield into a cautionary tale for foreign debt-financed takeovers in English football.
“On behalf of the entire Canadiens organization, I would like to extend my deepest condolences to George’s family.” — Geoff Molson
2. The Forced Sale to FSG for £300 Million in October 2010
In October 2010, following intense legal battles, Gillett and Hicks were forced into a sale worth around £300m to New England Sports Ventures. The selling pair openly insisted that the £300m valuation was far below the club's true market worth, but creditors forced the transaction through.
It ranks second because it brought a definitive end to three chaotic years that severely damaged Liverpool's executive reputation. The dramatic High Court proceedings marked one of the most high-stakes corporate showdowns in Premier League history.
1. Reshaping Liverpool's Modern Trajectory and FSG Era
The tumultuous departure of Gillett and Hicks directly enabled John Henry and Fenway Sports Group to assume control of Liverpool FC in late 2010. That high-stakes ownership transfer ultimately laid the structural foundation for Anfield's modern renaissance over the following decade.
It takes the top spot because no single sequence of events in modern Liverpool history created a more profound long-term transformation. While Gillett's era was defined by conflict, his exit opened the door to an era of European and domestic silverware under FSG.
Honorable Mentions
Honorable mentions include Gillett's early broadcasting investments, his various local philanthropic efforts in Quebec, and his secondary commercial investments across North American motorsport. While these projects demonstrated his broad business reach, they lacked the global drama and lasting impact of his time in Montreal and Merseyside.
