Dick Advocaat brought the good times back at Glasgow Rangers following the demise of the legendary nine-in-a-row side.
The 1998 appointment of the Dutchman gave the Ibrox side a new lease of life, as they embarked on a trophy-laden two-year spell, winning five out of the six domestic trophies available to them.
It all started to unravel in season 2000/2001 however, with Celtic, having appointed Martin O’Neil as their new manager, sweeping the board, and leaving Rangers to lick their wounds.
The Dutchman’s transfer business was also poor that season, with one particular signing proving to be a giant waste of money…
Rangers signed Gayle from Wimbledon for a fee of £1m, a decent sum for a 30-year-old approaching the end of his career.
His arrival in March 2001 meant he only had a few matches left of the season to prove his worth to Advocaat, but the Englishman didn’t exactly get much of a chance.
As quick as he arrived at the club, the striker was departing, with Watford sealing a deal to bring the Jamaican international back to England for £900k and playing for another 6 years.
It was a strange transfer and there is no doubt if he had been given longer, Gayle would have showcased his goalscoring abilities.
The 52-year-old looks back fondly at his time in Glasgow however, saying:
“I could probably have done with that move two years previously but I cherished the experience I had.”
Who knows what might have happened had he moved while at the peak of his powers back in 1999, but Advocaat made a big howler by bringing him to the club.