Men in Blazers holds the position of the biggest independent football-centred media business in North America, yet this week its founder and chief executive Roger Bennett was finally able to return home.
What began as one podcast has expanded into a comprehensive digital network, delivering football content throughout the year via three principal channels. The output includes daily podcasts, video content in both brief and extended formats, social media activity, email newsletters, companion viewing experiences for matches, touring live events, and volumes that have reached bestseller status with the New York Times. Furthermore, the Men in Blazers television programme broadcasts immediately following Premier League fixtures on NBC and Peacock.
The previous weekend marked the first occasion the network transmitted live football, as Tottenham Hotspur faced Hoffenburg in a friendly that reached audiences across the United States and Canada via the Men in Blazers YouTube channel. However, as Bennett prepares for an intensive schedule visiting Premier League clubs ahead of the new campaign, one particular moment stands out as his personal highlight.
On Monday, the devoted Everton supporter delivered a live programme at Hill Dickinson Stadium, with his mother present in the audience for the first time. He conducted interviews with first-team squad members James Garner, Hayden Hackney, Christian Norgaard and Kiernan Dewsbury-Hall, while approximately 200 additional Toffees enthusiasts, along with chief executive Angus Kinnear and technical director Nick Cox, also attended.
Before the event, Bennett, who arrived in the world in Liverpool on September 14, 1970, relocated to Chicago in 1993 initially on a brief tourist visa before eventually settling in New York and obtaining American citizenship in 2018, sat down for a detailed conversation with his local publication.
Recalling his earliest Everton memory, he informed the ECHO that he can still recall the initial match he attended on April 1, 1978, when Everton defeated Derby County two goals to one. He visited Goodison Park yet could not see anything at all.
The match started at eleven in the morning due to it being Grand National Day, and conditions were freezing. A man seated beside him removed his sheepskin coat, placed it beneath him to boost his view while lifting him with one arm and stated in a broad Scouse accent that the club represented one big family at Goodison, and from that moment he was hooked.
He remembers every detail. Every child recalls the first time they glimpse the playing surface and floodlights, the distinctive combination of spilled beer, perspiration and police horse manure.
The cold was intense, and during the interval someone somehow produced a flask of Bell’s Scotch whisky and instructed him to take a drink. That warmth spread through his entire body, and he has been a whisky drinker ever since.
It was wonderful, it was captivating. Then, the subsequent campaign featured Andy King’s derby-winning strike. They were exceptional, with Bob Latchford being his absolute idol as he watched the team score thirty goals that season.
Fundamentally though, it was about attending with his father. He suspects many people can relate, but regardless of other circumstances in life, the stadium offered parents a place to lose themselves in something for ninety minutes.
It centres on the football and the victories. There are multiple layers to these memories, much of which involves family, and the two aspects exist together.
He represents the third generation of his family to support Everton. His grandfather was a Toffees fan, his father was a Toffees fan, and as a child he believed the club was enormous, and indeed it was.
His children all follow Everton but have not witnessed what he experienced since the team has not been the finest in England or Europe for some time. However, it remains his lasting hope that they will be again during their lifetimes.
He travelled across the continent with his children following the team. Everton commanded recognition, respect and fear throughout Europe.
Watching them approach the threshold of becoming one of Europe’s elite felt like an unfinished story. Supporters have waited a considerable period for that status to return.
Despite residing predominantly on the other side of the Atlantic throughout the Premier League era, Bennett maintains that through frequent visits to attend matches, Everton has preserved the traditions that define the club.
The experience of attending Everton Football Club remains incredibly powerful, even at Hill Dickinson Stadium, which resembles a spacecraft having landed on the Mersey’s banks. He feels tremendous pride that Everton has managed to elevate standards while retaining tradition, authenticity and a strong sense of place.
That quality makes Everton special to him in 2026. The sport has become global, yet many American visitors find this to be the most compelling atmosphere, Everton and Crystal Palace specifically, and the matchday experience at the new venue maintains that authentically local feel.
On one hand, the past three decades have been difficult, yet the beauty of football lies in creating your own path and using it as a perspective on life, and Everton has always been that for him. The club offers so much, even during testing times, and there have certainly been genuine difficulties, but the supporters’ spirit represents the finest qualities of the sport.
At certain moments, the supporters have been instrumental in rescuing the club. Their principles include devotion, resilience and unwavering faith.
This applies to the relegation struggles under Sean Dyche and even the Paul Gascoigne and David Ginola period of the early 2000s. Then when something positive occurs, such as Denis Stracqualursi finding the net, celebrations resemble wedding dances.
Frank Lampard’s Great Escape provided similar scenes. It seemed absurd, yet it was wonderful.
The bolt cutters, the dog being carried through streets outside Goodison, discovering strength and goodness and collective spirit during genuine hardship.
That represents the greatest privilege of being an Evertonian. Nothing is taken for granted.
For him, it transcends football and offers lessons for life itself.
Sitting in the refined surroundings of The Yard within Everton’s striking new 52,769-seat home on the Mersey waterfront, designed by American architect Dan Meis, what are his thoughts on Hill Dickinson Stadium?
The first occasion he entered the home changing room made the greatest impression. Roberto Martinez used to explain that when attempting to sign players for Everton, he would meet them at Finch Farm or the airport, because bringing them into the Goodison Park changing room would guarantee they would not commit.
Witnessing excellence return to Everton is wonderful. Goodison Park, which he frequented during that final season, holds tremendous beauty, especially towards the conclusion when individuals purchased individual match tickets and attended alone.
The last fixture he attended was against Ipswich, and a woman sat by herself. When Z-Cars played, she began weeping, clearly grieving a parent she had recently lost.
A fellow supporter placed his arm around her and asked why she was crying when the team had not even suffered defeat.
That final chapter held genuine beauty. Hill Dickinson Stadium, he hopes, resembles a butterfly entering a cocoon, with something wonderful emerging over the coming seasons.
It represents a declaration of ambition. Hopefully, the reality will align with that statement.
With the transfer window still active and the season’s commencement imminent, recruitment demands attention, yet having visited various domestic competitors this week, Bennett believes fellow Toffees supporters are not isolated in their concerns and hopes regarding new arrivals or those still awaited.
Taking a broader view of football as a whole, it represents a summer of upheaval. Nine fresh managers now work in the Premier League, with the World Cup having disrupted the transfer market and made the window uncommonly late for every club.
He has spent the week visiting numerous clubs, covering Chelsea, Arsenal, Tottenham and Manchester United, with filming occurring at each. Every organisation feels similarly unfinished, with everyone communicating that additional business is anticipated.
This creates considerable frustration for all involved, supporters and managers alike.
The sport operates as an interconnected system, and financial regulations restrict possibilities for clubs such as Aston Villa, Newcastle United and Everton, which find themselves in comparable positions. When combined, this creates genuine anguish.
With limited days remaining in the summer window, there are questions about what the starting eleven might look like against Crystal Palace.
Despite Bennett’s optimistic outlook and his commitment to extracting positivity from even brief football moments, someone old enough to recall Everton as the nation’s premier team on multiple occasions carries the frustration of a trophy drought, shared by countless other devoted but patient supporters.
He acknowledges having a rather dark side at times, occasionally believing only Everton Football Club keeps him afloat. He desperately wants to witness Everton claim a trophy once more before his time ends.
Observing Crystal Palace and the happiness they have experienced demonstrates what is possible. Yet he maintains that football encompasses more than silverware.
It involves connection, generational bonds and memories. His numerous connections to this club provide tremendous energy.
Everton has taught him to discover happiness wherever it exists. It serves as an ideal approach to navigating this unpredictable world.
Beto’s goal-scoring represents this philosophy. His happiness and his path from employment behind a KFC counter to netting Premier League goals.
Kiernan Dewsbury-Hall, a late developer in the sport following a late growth spurt, arriving at the club and stating this represents his finest football and connecting with the supporters.
When he watches Iliman Ndiaye, with his father no longer present, he reflects on all the players his parent adored. While watching matches, his father’s voice remains in his head, recalling wingers such as Dave Thomas, Alan Irvine, Pat Nevin.
Results do not always go as hoped, yet it is the layered memories from watching and the fleeting happiness that matter. Securing a trophy would only enhance that experience. He would seize any opportunity for Carabao Cup success.