Plymouth Argyle may look at Millwall with a tinge of regret: View | OneFootball

Ryan Leonard played just 17 minutes for the Pilgrims before being released as a teenager

This summer marked six years since Ryan Leonard first moved to Millwall, with the defender racking up over 150 appearances for the club since his arrival in South London.

The 32-year-old has 400 league matches under his belt for Southend United, Sheffield United and the Lions, with just a single appearance for the club where it all began for him: Plymouth Argyle.

Having had a bright career across all divisions of the Football League, the decision to let the tenacious full-back leave Home Park in the summer of 2011 will still wrangle with some Argyle fans, as one of their own escaped the net and carved out a career of their own.

With the Greens going on their own journey up and down the divisions in recent years, having another homegrown talent in the ranks could have been the difference when the going got tough, instead of seeing him flourish further afield.

Ryan Leonard fails to make the mark at Plymouth Argyle

A 2-0 defeat to Blackpool at Home Park in March 2010 may not register prominently in many Argyle fans’ minds, but for Leonard it had a lot more meaning.

For 17 minutes on that Saturday afternoon, the defender was a fully-fledged Argyle player, playing in a Championship game for his boyhood club for the first - and what proved to be only - time.

Reminiscing on the moment with the Argyle Podcast, Leonard said: “I remember it was 0-0 and we lost 2-0 after I came on, that’s what I think about now.

“I look back now and it’s so disappointing, I know I made my debut at 17 in the Championship and it was a great moment with all my family there watching, but I still think about now that we lost 2-0 that day.

“It was a case of the adrenaline that I had going onto the pitch is something I had never felt before, and I don’t think I’ve felt anything like it since to be honest, it was an incredible moment, and a moment that I will never forget."

But that glimmer of hope proved to be a false dawn for the then-teenager, with the a never-ending wait to put on the green shirt once again, with Peter Reid deeming him surplus to requirements in Devon 16 months later.

With the club facing financial difficulties and the threat of extinction, the decision was made to let Leonard go, with the homegrown talent left devastated as his club limped on without him

He continued: “I was gutted, there are moments in your career that are pivotal, and that was another one when they said I could leave.

“I was more surprised than anything else, one at the timing of it, and two, with the situation the club were in, I really thought I could offer the club things.

“I know I was young, but I thought I had a good chance of having a good few years at the club and helping them get back to a better situation.”

That decision is one that would come back to haunt Argyle in the years to come, with Leonard still competing at Championship level all these years later, as Argyle finally caught up after their promotion back to the second tier in 2023.

Ryan Leonard becomes, Southend United, Millwall mainstay

Tasked with trying to rebuild his career after his Home Park departure, Leonard eventually found his way to Southend United in League Two in the summer of 2011, with Roots Hall proving to be somewhere he called home for the next six-and-a-half years.

With Argyle in free fall themselves, it didn’t take long for the two to be reacquainted, with the Pilgrims travelling to Essex the following September, with Leonard getting one over on his old employers in a 2-0 victory.

Time and time again the defender would perform admirably on his returns to Home Park, as the Greens continued to stave off both the administrators and relegation, while Leonard was heading to bigger and better things.

Promotion with the Shrimpers was assured in the 2014/15 season, and with three years in the third tier under his belt from then on, a move to Sheffield United in the Championship followed.

Although the link-up with the Blades was relatively short-lived, it paved the way for the next move in his career, with Millwall the next side to take him under their wing, which is where he has stayed ever since.

In the time since Leonard has called The Den home, Argyle have been relegated once and promoted twice, as they finally secured a return to the second tier after claiming the League One title in the 22/23 campaign.

And who was there ready and waiting upon their return? None other than Leonard, who has since established himself as a regular for the Lions, with his match-winning attitude endearing himself to the South London faithful.

A return to his old stamping ground last October proved to be a fruitful once, as he gave the Green Army their latest reminder of what could have been, with the Lions emerging 2-0 winners from their trip to Devon.

All Argyle fans could do was watch on and wonder what might have been, as one of their own continues to plough their own farrow in the big city.