Like the London club are right now, Leeds were the team to watch around the turn of the Millennium.
Packed full of exciting talent and providing a host of players for the England national team, the Yorkshire club cut a swathe through the top end of the Premier League and then followed that by doing the same in Europe.
O’Leary’s talk of his “babies” may have begun to grate long before the Irishman finally dropped the label, but there is no denying just how bright the future once looked at Elland Road.
Manchester United and Arsenal, the two standard bearers in English football back then, were genuinely worried about a team that, like Spurs under Pochettino, seemed the ideal fusion between homegrown talent and inspired imports such as Rio Ferdinand and Mark Viduka.
Runs to the semi-finals of the UEFA Cup and Champions League sandwiched a third-place finish in the league, fuelling the belief that United’s time had arrived.
The reality, of course, proved rather different with the ‘Millennium bug’ that was supposed to lead to planes dropping out of the sky and computers crashing across the globe instead claiming United as its major scalp.
Tottenham, thanks to Daniel Levy’s business acumen and the Premier League coffers swelling more and more with each passing year, will not suffer the sort of financial collapse that once befell Leeds.
But if Pochettino persists with his belief, aired again this week, that the lifting of the FA Cup will change little at Spurs then there is every chance he will one day emulate O’Leary as one of English football’s nearly men.
The Irishman did so much good at Elland Road. For a start his side was wonderful to watch. He also gave supporters memories that will last a lifetime, particularly in Europe where United looked every bit at home in the magnificent football cathedrals of the San Siro and Bernabeu.
Even a 4-0 hammering in the Nou Camp was followed two or so months later by United knocking Barcelona out of the Champions League group stages.
Almost a generation on from those glory nights, however, and what do the club have to show for such an admittedly exciting time? No silverware, that’s for sure.
Reaching the last four in Europe two years running was laudable, but neither can be paraded from the top of an open top bus or shown off proudly in the boardroom. Nor will an anniversary dinner be held in their honour 25 years down the line.
Like Pochettino, there was a sense at Leeds under O’Leary that the domestic cups didn’t quite cut the mustard.
Get knocked out by Tranmere or Cardiff or Leicester and there were still bigger fish to fry elsewhere. United’s day would, instead, come in the Premier League or Champions League, competitions that truly mattered.
This ‘run before you can walk’ mentality ultimately ensured one of the most exciting teams to emerge in the Premier League era had to go elsewhere to win the medals their talents had promised at Elland Road. It would be a crying shame if the same is one day said about Harry Kane, Dele Alli et al.