Manchester City are playing Leicester in the League Cup, and he can’t help but keep a watchful eye.
“They’re beasts, aren’t they?” he says of Pep Guardiola’s side.
But it wasn’t always that way. Two decades ago, they weren’t even in the Premier League and would drop to the third tier of English football.
Conlon knows about that grim period, because he was there. Released by QPR in the summer of 1997, the teenager was picked up by City and Conlon walked into a club still reeling after its annus horribilis.
After top-flight relegation, what followed at Maine Road was chaos. The club bounced from one managerial crisis to the next. The squad was bloated and needed an overhaul. But City did retain the services of a cult hero: diminutive Georgian playmaker, Georgi Kinkladze.
“Leaving Carrickmacross, in Monaghan, just two years before, as a young fella who mostly had played Gaelic football — and now here I was, with players I’d watched on TV, like Kinkladze,” Conlon says.
“He was a genius footballer. He was just different. I would’ve been happy just warming up with him. But getting to make my debut, by coming on for him, was just crazy.”
One Saturday afternoon, in late September, City hosted Swindon Town. They’d managed one win from their opening seven games. So, manager, Frank Clark, threw the dice a little.
“I was playing well in the reserves and scoring goals, but I had tickets for an Oasis gig and was going to go along to it. Then, I got a call to say I was in the squad for the game,” Conlon says.
“We had the five subs, so I thought I’d be down the pecking order. I thought, ‘No worries about me coming on’ and then, at half-time, the gaffer says, ‘Barry, go get warmed up’.
“And I went out on the pitch and did a little bit and I’m sure the fans were wondering who I was.
“It is a bit like a dream. After I came on, the whole crowd started singing. ‘There’s only one Barry Conlon’. Everything had just happened so quickly. But it was a good feeling.”
He made an instant impact, too: just three minutes after coming on, he slipped through a pass for Paul Dickov to run onto. He squared it for misfiring striker, Lee Bradbury, who gleefully tapped home.
Clark gave Conlon more opportunities and he made a first start for the club in a loss to Port Vale. But, when struggling City appointed Joe Royle to try and stop the rot, Conlon was deemed surplus to requirements.
He tries to join the dots, regarding what came next.
There was a loan stint at Plymouth, before he cut his losses and left City for good, joining Southend on a permanent deal. After one season there, it was off to York.
And then, there’s a long pause.
“I lose track of where I’ve been sometimes, I’ve been around that much,” he says, laughing.
“Sometimes, you forget entire seasons.”
The plan was to drop down, impress at a lower level, and get a move to the Championship.
Maybe a Premier League team would even take a chance. He gritted his teeth and went to work.
Having scored goals wherever he went, Conlon impressed while at Darlington, and was crucial to the club keeping their league status. He signed for Barnsley and felt good. Things started well, but injuries were becoming more frequent and the vicious cycle of lower-league football began to cause problems.
“It was a case of the manager telling the physio, ‘I want him fit for Saturday – that’s it’. You want to play through the injuries, because you want to play as much as possible to get to where you want to be. I’d had a cartilage operation at Darlington.
"But I had to get another one at Barnsley. I woke up and the surgeon was there. They had to drill into the bones to make them bleed and it forms a fake cartilage. But it only lasts so long.
"He said to me, ‘Listen, I’d recommend you pack it in and retire. This will last you a year, but you’ll need a knee replacement then.’ I couldn’t handle it. I continued playing, but I knew there was no climbing back up the ladder after that.”
Conlon was still in his mid-twenties. But now, it was all about surviving.
“The head starts playing tricks on you,” he says.
“You feel guilty. I wouldn’t say you lose the love of it, but you lose a bit of heart. You’re letting people down and there’s nothing you can do about it. But I was telling myself, ‘You’ll get another season, another season’.
"There was no thought about the future. There was no other plan, except just to keep going. I knew I wasn’t the same player. You lose that half a yard. The movement isn’t as sharp. I knew it was only a matter of time. But I got six more years out of it,” Conlon says.
Conlon left Barnsley in 2006 and racked up a litany of short-term stints. After a successful spell with Bradford, his playing time began to decrease. Between 2009 and 2012, he played for six different clubs, including one in the Belgian third division.
"Growing increasingly disillusioned with his beat-up body and unable to come to terms with his career ending, Conlon started to make headlines for the wrong reasons.
“Nobody else knows you’re struggling to get your socks on in the morning. That you’re getting injection after injection just to keep going,” he says.
“You lose interest in everything around you. You’re going to bars more than you should be. I wasn’t right in the head. I can relate to how people finish playing and go through depression, even if you’re on five-hundred grand a week. That was when I got a little bitter about what went on.
“And I think it gave me some relief. Because you wonder, ‘Maybe I could’ve done more, maybe I should’ve gone there’. You look back at all these things. But I just wanted to be on the field.
“It was lonely at the same time, too. Sometimes, you got a bit of freedom going out on a Saturday night and just chatting to people. You might feel a little important, as well. You can look at it a hundred different ways.
“You read back over some of the stuff now and you feel the guilt of the silly mistakes. You’re in that bubble with 20 boys in the changing room every day, you can come and go as you please, and you’re probably still a bit of a child. You don’t grow up as much as your everyday man, who gets up and does their work.”
Conlon went back to Ireland in 2012, admitting it was “a shock to the system”. There was the comfort of being surrounded by family, but he never settled. He was restless. Still, he stepped out of that bubble he’d been in for so long.
“It was really hard to handle, but there is the realisation that there’s other stuff going on. It’s not just about you and football. It’s not the be-all and end-all. I wanted to find a path again, like I had before.”
He found it in New York. Visiting one of his brothers, he met Kim one night. Shortly after, he picked up coaching work through a UK-based company, who provided him with short-term visas and he was back and forth to the US constantly, until the pair got married last year and settled in Yonkers, about 15 miles outside Manhattan.
“Boy meets girl in an Irish bar,” he says with another laugh.
“Things started growing from there and you start to see things more clearly. It’s all about timing, I guess.”
He’s got the knee done too, finally. A replacement at 39. But he’s in the gym again and feeling good.
“The body’s back in shape and the mind’s back in shape. I couldn’t ask for much more now. Onwards and upwards. But what an interesting ride.”