But for work permit issues, Jovan Kirovski would have made it into the Manchester United first team after 1996.
The California born then USA international had been recruited by the club a few years earlier and developed in the youth teams at the same time as the fabled Class of 92 - indeed he and David Beckham would link up again at LA Galaxy more than a decade later - but as he told me on Team 33 this week, red tape put paid to the dream of wearing the jersey of Man United, even though he would later get to play at Old Trafford thanks to his former Red Devils team-mate and Birmingham City and Crystal Palace manager Steve Bruce.
You can listen to the full interview below (as well as a portion on childhood and great players from our August chat with the great John Giles) or stream/download for free on the iTunes Podcast App:
Jovan Kirovksi Interview: Robbie Keane greatness, Man United's Class of 92 and his Champions League win
Instead of playing for Man United, the now LA Galaxy technical director joined Borussia Dortmund at a very opportune time for the club.
Having joined in 1996, he made a couple of appearances home and away in the Champions League against Atletico Madrid en route to becoming the first American soccer player to win a UEFA Champions League medal as Dortmund overcame Juventus at the end of the 1996-97 season.
In the full interview, Kirovski chats about growing up in a USA not accustomed to soccer, memories of playing with the Class of 92 at United, the Dortmund adventure and the Irish team-mates he had done through the years like Phil Babb (Sporting Lisbon) and Robbie Keane (LA Galaxy).
He was especially complimentary of Ireland's record goalscorer with whom he worked with at Galaxy.
"He came in and he really was something special. Robbie Keane in my mind is the best player to ever play in MLS. His statistics shows it, he scored over 100 goals and he won three championships. There's not a player who's had his success. He's the best in the history of MLS," he told me, before giving an insight into Keane's leadership within the dressing room at the time.