DICK Advocaat will take on one of the biggest challenges of his career this week when Russell Latapy puts pen to paper on a two-year contract with Rangers.
Throughout his career Rangers' Dutch boss has revelled in his reputation as a tough disciplinarian and stories of his uncompromising ways are legendary among former players. His arrival at Rangers dovetailed neatly with the departures of a team full of 'characters' whose time keeping and other habits stretched their new manager's tolerance to the limit.
Neither Andy Goram nor Ally McCoist could be described as punctual but those little blemishes didn't prevent either of them from leaving Ibrox with a sackful of honours and international caps.
Charlie Miller didn't last much more than a year under Advocaat and only now, three years down the line, is he finally finding the form that earned him rave reviews as a teenager.
At the end of last season Jorg Albertz kissed an emotional good bye to the Rangers supporters, but the popular German never saw eye- to-eye with his gaffer.
To put it bluntly, it takes a certain type to find favour with the Rangers boss and on all known current form Latapy and Rangers appears to be a marriage made in hell.
Whether Latapy will reform or Advocaat will relent in order to indulge the midfielder's undoubted talents is the burning question as Rangers kick off one of the most vital season's in their recent history.
The former Trinidad and Tobago captain tested the patience of Alex McLeish to the limit during his three seasons at Easter Road, before big Eck finally ditched his problematic playmaker.
McLeish could have tolerated a drink-driving charge, a lot of bosses know the feeling, but a night on the town three days before a local derby finally snapped the Hibs' manager's patience.
Latapy gambled that Hibs couldn't do without his influential presence in the Scottish Cup Final against Celtic, but he badly misjudged McLeish's mood.
Tellingly, McLeish was already contemplating going into the final without his 'star' turn after becoming increasingly concerned by the 32-year-old's fitness and attitude.
"I was a little worried about Russell's overall fitness and I told him about it," the Hibs boss said at the time.
"He's obviously pressed the self-destruct button but I did say to him in a meeting before the incident that I thought his level of fitness was lower than the rest of the players.
"He assured me it would be okay come the final, but I said that I couldn't take that chance and that he had to be ready for our League match against Hearts.
"Russell is a super confident guy and he was adamant that he would be alright for the final. I don't think he thought that he wouldn't be involved, he just got caught up in something that he knows now he shouldn't have."
Accommodating the unorthodox within a team pattern is a massive test of management and one that most bosses decide to steer well clear of.
McLeish, only half joking, referred to one of Latapy's best friends putting in a claim for the axed midfielder's Cup Final tickets shortly after he had been jettisoned from Hibs' plans.
Latapy and his bosom buddy, Manchester United striker Dwight Yorke, have regularly been allowed to indulge on international duty before new national coach Rene Simoes decided to crack down.
In a move that Advocaat would probably admire, Simoes axed Latapy and Yorke from his side to meet Jamaica yesterday in a World Cup qualifier after the pair missed yet another training session.
Both players reported for back the following day but after a brief discussion with Simoes they announced their retirements from international football, citing a commitment to their club careers that hasn't always been evident.
Latapy and Yorke's wordy resignation letter, in which Latapy already considered himself to be a Rangers player read: "We wish to express our thanks and appreciation for the opportunity provided and the support rendered by members of the technical committee and the administrative personnel throughout our tenure on the national senior football team.
"It is thus with heavy hearts that we advised the technical director today of our decision to resign from the senior team with immediate effect.
"This decision, which we believe is in the mutual interest of all concerned, is due primarily to our personal commitments as well as the increasing and conflicting demands of our clubs, Manchester United and Rangers FC, and the national team.
"Special thanks are extended to the people of Trinidad and Tobago who have supported and inspired us throughout our careers.
"We wish to express our sincere gratitude to the soccer fraternity, and fans in particular and give our full support to the national team in all their endeavours."
Popping up in a Rangers shirt this week will certainly be an amazing turnaround for Latapy after falling foul of both his old club and country within the last two months.
Repeatedly linked with a move to Celtic before opting for Rangers, it remains to be seen whether the Bhoys have missed out on a bargain - or had a lucky escape.