In June 1990, just minutes after his shocking first-round defeat to upset specialist Derrick Rostagno at Wimbledon, a suddenly aging and forlorn John McEnroe sat down with NBC’s Bud Collins, along with rival Jimmy Connors, for an interview. Connors was working for NBC that summer as an analyst while nursing a wrist injury.

It was a rare moment of revealing, subdued reflection from the usually fiery McEnroe. The loquacious New Yorker spoke about his disappointment with himself and his level of play and how difficult it had become to balance family life and a pro tennis career. Connors pointed out that his fellow Irish-American seemed to be lacking direction and was in need of advice on how to proceed.

And then something extraordinary happened: Connors offered to be the one to guide McEnroe back to glory by suggesting he himself step into the role of McEnroe’s coach. McEnroe literally extended his hand to seal the deal and for a brief moment the impossible was about to happen: two fierce – and often hated – on-court rivals were about to team up and give their tennis generation one last chance of glory before being rudely – and permanently – kicked out of the party.

But, alas, it wasn’t meant to be. Those few minutes were as far as the coaching proposition went. Years later Connors would remark that shortly after the interview both he and McEnroe decided “to run the other way”.

I couldn’t help but think of that might-have-been moment when the shock announcement came last week that Andy Murray would be teaming up with Novak Djokovic, serving as the Serb’s coach to start the 2025 campaign. The brilliant Djokovic will be seeking his 11th Australian Open title in January and, what is likely even greater motivation, his 25th major title overall which would allow Djokovic to surpass Margaret Court as the all-time winning slam champion, man or woman.

In some ways Murray’s coaching of his longtime friend and rival makes sense as the two have been joined for decades. Consider: Roger Federer is six years older than both Murray and Djokovic and started in an entirely different tennis generation. Rafael Nadal had such unprecedented early success that he separated himself from his slightly younger rivals early on and solidified his pairing with Federer as early as 2004. But Murray and Djokovic have a history that extends back to when they competed frequently in their junior days. And they were also born days apart from each other in May 1987.

Further, though Murray is a three-time slam champion himself (impressively twice beating Djokovic in major finals), and a surefire Hall of Famer, his relationship to Djokovic, as opposed to McEnroe and Connors’ fractious interactions, was never one of co-equals; Djokovic, Federer and Nadal are obviously in a world of their own and the whole notion of there ever being a “Big Four”, as it was coined early on, was false, as well as an unfair burden on Murray. There was the Big Three with an occasional plus-one (that “one” being either Murray or Wawrinka).

Being that he was a great player in his own right, it’ll be interesting to see what Murray can do to help Djokovic get that one last slam before he retires as perhaps the greatest player of all time (if one is judging it solely by the faulty metric of slam titles). Murray just may be able to provide that little bit of a mental edge or confidence boost that Djokovic needs, something that – perhaps – only another former top player can provide. Djokovic has tried this previously when Boris Becker assisted his coaching team for several years with much success.

Maybe Murray will be able to channel the positive effects that his former coach Ivan Lendl had. Lendl is that very rare breed – someone who was an all-time great on the court and also reached huge success as a head coach, guiding Murray to all three of his slam triumphs. But Lendl is indeed the exception that proves the rule.

The sporting world is littered with great players who couldn’t transfer their successes from the playing arenas to the coaching box. Consider Ted Williams. Inarguably the greatest hitter to have ever lived, Williams was also a passionate teacher and he fulfilled a personal dream when he became the manager of the less-than-mediocre Washington Senators in 1969, winning the Manager of the Year award his first year. But the perfectionist Williams soon discovered how difficult it was to instill his preternatural baseball abilities into subpar talents. During his four years at the helm in Washington (and Texas, where the Senators were and relocated and renamed the Rangers), Williams finished with a career won-lost percentage of .429 – lower than his career on base percentage as a player, .482.