James O’Connor: From breaking through at Stoke to coaching Orlando City

The tongue-in-cheek saying, ‘Could he do it on a cold Tuesday night in Stoke?’ has become widely used when debating whether footballers could adapt to the conditions of the English game.

Fortunately, having hailed from Dublin, James O’Connor was already made of tough stuff by the time he crossed the Irish Sea to link up with the Potters’ academy as a 14-year-old in 1994. 

After progressing through the youth system at the Staffordshire club, James went on to lift the 2000 Football League Trophy before playing a key part in Stoke’s promotion to the Championship in 2002, where they overcame Brentford 2-0 in the play-off final at Cardiff’s Millennium Stadium.

“It was an incredible experience,’ said O’Connor.

“My wife’s family are from Stoke and we still have a number of family members in that area.

“It’s a club very close to my heart, and I think anyone would tell you, there’s a natural affinity to you first club, especially if you come through the ranks.

“It was phenomenal for me to break into the Stoke first-team and then go on to help the club gain promotion.

“I always look for Stoke’s results, and I keep track of how they are getting on.

O’Connor went on rack up over 500 appearances in English football at the likes of West Bromwich Albion, Burnley, Sheffield Wednesday and represented Ireland at Under-21 level, before hopping on a plane across the pond to culminate his career in the sunshine at Orlando City.

However, like any top-class footballer during a match, the Irishman was always thinking three steps ahead, ensuring his time in football did not end the moment he played his last match.  

When he was not snuffing out counterattacks and shackling strikers on the pitch, James would be, well, on another pitch studying the game from a coaches’ perspective and expanding his knowledge.

“Any sports person would tell you that when you are obviously very ambitious, the biggest thing you want is to be in an environment that will garner success,” he said.

“I was fortunate to have played under lots of managers over the years, and we were able to garner some success.

“There were some years where things maybe did not go the way that we wanted, but I think the biggest thing for me is to always be learning.

“Even as a player, I was always taking notes on different cultures, different managers, different training sessions and all the other different ways and situations they had to handle.

“Having a growth mindset is very important, and it is always something I have had from a young age.

“I was doing my coaching licences in my early 20s and then I had my pro licence by the time I was in my early 30s – it’s something I have always taken very seriously.”

While so many players move away from the game upon retirement, O’Connor was already planning, expanding his knowledge, ensuring he was ready for any and every opportunity which presents itself – preparation was of paramount importance.

“I’m so passionate about the game and I always want to get better and improve.

“I think it is something ingrained into my family, who then helped ingrain it into me. My family always wanted to strive to be the best that they could be.

“I looked at coaching to get better as a player, as a way of getting a better understanding. It did not always work that way, but my intention certainly was to learn as much as I possibly could.

“I am a big believer in trying to learn from my own mistakes, but also from other people’s.

“Life gives you a wonderful opportunity, so if your eyes and ears are open and you have a growth mindset, there is an awful lot you can learn.

“We all must intend to have that mindset.”

While it has been seven years since James’ final match, a 1-1 draw away to the Rochester Rhinos, his dedication to learning and development suggests he still considers himself a student of the game.

O’Connor in action for Burnley (above).

“I have always wanted to develop and expand my knowledge,” explained O’Connor.

“Initially I started with the coaching certificate, then I did the UEFA B and then the UEFA A licences.

“I just wanted to get through the licences as fast as I could and learn as much as I could.”

These licences were all achieved while he was still donning the blue and white of Sheffield Wednesday.

While most players wait for their footballing careers to reach their respective nadirs before even considering a career in coaching, O’Connor was almost ready for full-time management during his prime playing years.

“Steve Cotterill always encouraged and guided players like me to get their coaching licences,” he said.

“His attention to detail was fantastic, and there are so many managers you look back on who were really intelligent individuals with outstanding football brains.

“The biggest thing for me as a young player was to just try and learn as much as I possibly could.

“Even now, we encourage our players to go out and get their licences, because I think it’s really important to educate yourself – better coaches can be better players.

“I believe quite often when players retire and they become coaches, there are definitely scenarios where they think ‘I wish I’d known this when I was younger, I wish I could have implemented a little bit more’.”

Having navigated his way through the coaching badges at a similar pace to which he burst through the youth ranks at Stoke, O’Connor threw himself into a brand-new culture when Gary Mellor, senior partner at Beswicks Sports and one of the founders of Orlando City, convinced O’Connor to make the move to the United States.

O’Connor crossed the Atlantic after a 15-year-career in England.

“At that point I think I had amassed around 500 games in England, so when I came towards the end of my contract with Wednesday, it became very much a case of ‘okay, what’s the next challenge?’”

“Orlando were striving for the MLS and Phil Rawlins was there, who I have always had a great deal of respect for.

“I saw it as another opportunity to go and maybe do something a bit different and gain another piece of success myself.

“Learning a different culture and getting a better understanding of mentality, certainly in that phase I wanted to be looking at where all my coaching opportunities could come from.

“I saw America as a place where that could happen and Gary (Mellor) played a key role in that.

Beswicks Sports, who continue to represent and support O’Connor to this day, played a key role in identifying his next steps after his retirement.

“All the Beswicks guys have looked after me for years and they are great guys.

“Their knowledge base and their connections not just in England, but around the world, were something they were able to tap into.

“When a player starts off in their career, they think ‘okay, great, I need to play as well as I can to climb as high as I can, then I need to progress and achieve different things’.

“Then the next phase is, for some players, a change of industry, whether it is coaching, management or something else.

“I think the guys were very intent on sitting down, creating a plan and asking ‘where do you see yourself in five years’ time? What would you like to achieve?

“They were fantastic when it came to facilitate that and they continue to offer great tutelage and advice.”

O’Connor retired from playing in 2014 and then very quickly became the manager of Louisville City.

He managed them over four successful seasons, winning the USL Cup, USL Eastern Conference play-offs and finishing runners-up in the USL regular season three years running.  

“At the time I had spent about a decade just learning and preparing myself,” said O’Connor.

“I am a big believer in preparation, and I wanted to make sure that I gave myself every opportunity to prepare as well as I could.

“I think we were very fortunate with the ownership group in terms of the support we were given, as well as the amount of time we were given to implement some of our plans and philosophy.

“I think it worked out really well and we had a lot of consistent results which were very enjoyable.

“We also worked with some amazing people, from the owners to the front officer staff and to the players – it was a fantastic experience.”

After an impressive first spell in the dugout, James made the 900 mile journey back south to Florida as he was appointed head coach at his last playing club, Orlando City.

Unlike when he had been with the Lions as a player, the club had become a fully-fledged MLS franchise team in 2015. 

It was a step up from the USL Championship for O’Connor and, unfortunately, he experienced a sterner test.

Despite leaving the club after just one season in charge, James looks back on his spell with a level head.

“Anytime a coach goes into a job, there is obviously something wrong,” he said.

“When we initially got there, we were trying to set a plan out and put some infrastructure in there, as well as some philosophical pieces we needed.

“The opportunity came about really quickly and it was something we saw as a next step, another opportunity.

“We felt it was the right time to move and unfortunately it did not work out the way was wanted, but it still felt like the right time to go.”

The experience, which happened to James in his late 30s and just his second as a number 1, could’ve easily had a knock on effect when it came to his long-term ambitions.

However, O’Connor viewed it as a learning curve and wasted no time in identifying his next opportunity in the game.

So off he went, back again to Kentucky and Louisville City, where he stepped out of the coaching hotseat to take up the role as Executive Vice President of Development in January 2020.

James’ long-standing studious attitude on all aspects of football meant he nurtured a knowledge and versatility which allowed him to transition from dealing directly with players, to taking on more responsibility in the overall running and progression of a club.

“I think my experience and expertise from playing, coaching and managing has been developed and honed.

“This gave me an opportunity to learn even more new skills from a philosophical standpoint. It’s about how can I assist, how can I see a bigger picture?

“We brought in a great academy manager in Mario Sanchez, and we launched the brand new academy last July, which had at that point 44 teams.

“We had a women’s team that we were preparing for, so we had to bring in more technical staff and then launch a brand new women’s team who actually play in the highest league.

“From a training ground perspective, which is where we are now, it’s a $15 million dollar project with three grass fields and then a 31,000 square foot building.

“Every day I ask myself ‘what are the needs of the different teams we have?’ and ‘how can we give support to them the best possible way?’”

Despite making a success of the job since taking up the role 18 months ago, O’Connor, who has attained US Citizenship, is still determined to continue learning and developing.

“I’m trying to get on a sport directorship course which is being run in Miami,” he said.

“I’m a big believer in education, and that is something I want to do to increase my knowledge.

“I am always asked ‘are you going back into coaching, do I miss coaching?’”

“I think my experience at Orlando proved I just wanted to be around good people.

“Working in an environment where I can build trust to execute projects and really help people is the biggest thing for me.

“It means I can drive as hard as I possibly can and continue to educate myself and be the best version of myself every day.”

O’Connor’s vast experience culminating in many different roles acquired through talent, and being part of Beswicks’ transatlantic network, means he has had to wear many different hats in playing, coaching and club management positions.

Whether it has been captaining a team on the pitch, making big coaching calls from the touchline, or taking a whole football club into the future, each highlight the Irishman’s leadership qualities and real passion to educate others. 

So although that makes it tough to predict the next step and location on O’Connor’s versatile footballing journey when it arrives, his track-record, experience and knowledge will mean he has the tools to create another success story.