Trevor Sinclair's career is full of highlights - becoming Blackpool's youngest ever player when making his debut aged 16, playing for England at a World Cup, scoring the first goal at what's now known as the Etihad - but like all footballers, there were obstacles along the way.
The BBC pundit recently broke down a few of the difficulties he faced as a professional footballer and how he overcame them.
Embarking on a career in football during the 1980s was difficult for a young black player from Manchester.
"There was a lot of racism not just in football but in society - so there were a lot of trials and tribulations there as a young person," he said.
"I always used that as a tool to give me a bit more fuel for my fire, to push me on a bit further. "
Joining a club in the lower divisions
Sinclair enjoyed his time at the Bobby Robson School of Football, where he'd won a scholarship aged 14, but upon leaving at 16 the future England player chose a different route to many of the other students he'd been boarding with.
"Most of the lads I used to board with went to Manchester United, Arsenal, Tottenham, Liverpool - top teams around the country.
"I don't think it was frowned upon but I think a lot of people were quite surprised I'd chosen to go to quite a low club."
It turned out to be a good decision, with Sinclair making his Blackpool first team debut in the first game of the season that he joined, becoming the club's youngest ever player at the time and going on to make 112 league appearances. He's since been inducted into the club's hall of fame.
A particularly tough defeat
Sinclair's best performances arguably came in a West Ham shirt, under Harry Redknapp, in a team that included the likes of Rio Ferdinand, Frank Lampard and Paolo Di Canio.
But that team was on the receiving end of a demoralising defeat at the hands of Tranmere Rovers in the FA Cup.
"It was one of them times when you had to pull your sleeves up and look in the mirror. I found a lot of strength in the fact I could bounce back from such a difficult result and performance," he said.
Alongside injuries, defeat and falling out of favour, footballers have to deal with everyday life in the same way as the rest of us, only while having to try and perform to the best of their ability in front of thousands of people each week.
"The biggest low was when my mother died," Sinclair said. "I've probably not had the best things to say about Stuart Pearce as a manager or a team-mate, personally, but he had a lot of compassion at that time and gave me all the time I needed to get over one of the lowest points you can have in your life, let alone in football.
"I rolled my sleeves up and at the end of that season, I left City and went to Cardiff."
Losing a cup final
Sinclair played in some great teams but ended his career without a medal - the closest he came was right at the end of his career, when playing for Cardiff.
It was the pundit's second time playing at the new Wembley, following the semi-final, and fulfilled a dream to play at the stadium after winning England caps at a time when the ground was being refurbished.
But despite the talent of the team - Jimmy Floyd Hasslebaink led the line while a young Aaron Ramsey made an appearance - they went down 1-0 to a Nwankwo Kanu goal for Portsmouth.
"It was ups and downs but mainly I look back at the game with a huge smile on my face," he said. Definitely bittersweet.
Trevor Sinclair is part of the BBC's FA Cup 2016/17 presentation team. Watch Macclesfield Town V Oxford United in the FA Cup 2nd round live on BBC Two at 19:55 on Friday 2nd December.