Insider Sport’s Matchday Programme offers a personal look at what sporting moments and figures have inspired industry stakeholders. Through candid reflections, the programme delves into the stories behind the inspirations that have shaped their perspectives and fuelled their passion for sports. 

In this edition, Andrew Grimshaw, Commercial Director at Checkd Dev, reflects on the spectacular career of Muhammad Ali, speaking on his ‘winning mindset’ and his ability to deal with the immense pressure he faced at a transformative time in sport.

Andrew Grimshaw, Commercial Director at Checkd Dev

Which athlete do you think demonstrated the best winning mentality throughout their career?

Muhammad Ali. A unique boxing talent with outstanding character. Although he was before my time, I’ve watched plenty of footage and read various books to learn about this true sporting great. His self-belief was unparalleled. Ali’s career spanned a transformative era in sports, where media and money began to play a role forming the foundation of what today’s world of sport has become. 

He was a pioneer of the ‘winning mindset’ in sports too. His ability to overcome adversity, both inside and outside the ring, set a standard for mental toughness and determination. What a boxer and what an amazing human being.

Who was your childhood sports hero and why? Which of their sporting achievements had the biggest impact on you?

As an avid Manchester United fan who attended every home game as a kid and most away games as a teenager too, my hero was Bryan Robson. Known as “Captain Marvel,” Robson was an outstanding footballer – tough, super fit, intelligent, and a complete leader on the pitch; he is also United’s longest-serving captain. 

He took no prisoners and scored vital goals for United at a time when our arch-rivals Liverpool dominated. His resilience and leadership definitely had an impact on me, for me he epitomises the spirit and passion of Manchester United. United grew stronger later, but his role in bringing the Premiership, FA Cup and the European Cup Winners Cup to Old Trafford laid the foundation for what became the dominant period in United’s history under Sir Alex Ferguson. 

His performance against a Barcelona side including the great Diego Maradona, which United won 3-0, is the stuff of legends. Those that know, just know.

What sports team do you follow the closest? Is this a family team or local side etc, and what has been the biggest moment in your history of supporting this club?

I coached a local youth side in South Manchester for 10 years and they meant a great deal to me but I’m a third-generation Manchester United fan from Manchester. Including my son, now in his early twenties, we’ve watched United as a family for over four generations, spanning over 100 years. 

I worked for the club in a commercial capacity during the late 90’s too, giving me a behind-the-scenes look at the organisation. There was a time when United was everything to me – my religion. I’ve travelled across the UK and Europe, supporting the team through countless games in the 90s and 2000s. 

Although my passion has somewhat eroded over the last decade due to ownership issues and poor decision-making, the greatest moment for me remains the 10 days at the end of the 1998-99 season. Attending those key games and witnessing the goals from the “SAS” was unbelievable. No one will win a treble like that again. It was truly astounding.

Is there a team manager from any sport, whether that be football, rugby, NFL, NBA etc, who you think demonstrated the best leadership qualities?

I primarily follow football and then a bit of boxing with a bit of horse racing, so my passion and knowledge are limited to those areas. Alex Ferguson therefore is the manager that demonstrated leadership qualities beyond the pale. 

While I do watch other sports, to be honest none of the managers in other sports have had the same impact on me as SAF. His man-management skills are recognised enough already, just had that knack of getting the best out of a very wide range of personalities over a long period of time too.

What sports tournament do you think consistently provides the biggest thrills? Which moment from this league stood out to you the most in recent memory?

It’s subjective, but for me, the thrills aren’t as prevalent these days and not just because of the decline of my own club. I find money, VAR and the politics around football frustrating. I do still enjoy a great game of football, unsurprisingly the Premier League is the main sport/league I consume, but the last few years have been relatively predictable with a state-owned football club dominating. 

This season though the excitement of the 4-3 win over Liverpool in the FA Cup was the highlight.

If you could travel back in time to any historic sporting moment to watch it then and now, which would it be and why?

I would have loved to attend the 1968 European Cup Final. Witnessing Sir Matt Busby rebuild Manchester United after the Munich disaster and then win that trophy would have been an incredible moment. Seeing the one and only George Best at his athletic peak would be a dream come true too.

If you could go out for dinner with any sporting figure, current or historical, who would it be and what would you want to learn from them?

Think it would have to be the one and only Muhammad Ali. I would love to learn more about the man, about his mindset, his experiences both in and out of the ring, and how he dealt with the immense pressures he faced. His insights on life, sports, and of course his genuine humour, intelligence and charm would make a fascinating enjoyable dinner conversation.

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