Former lead principal of Jamaican investment house Stocks & Securities Limited (SSL), Hugh Croskery, has found himself in a bit of a pickle.

Wanting to do the right thing finds him in contention with a number of parties who were once very close to him

What road does he now take? Which will prove the less bumpy and be a path to redemption?

He owes his former partner George Chai and agreed to hand over a property in Discovery Bay in lieu of not settling the debt.

Croskery’s home in Norbrook has already been sized up.

Chai was a major shareholder of SSL and it appears lent Croskery the money when the company’s position became dire.

Clarifying the situation, Chai’s lawyer said: “George negotiated with Mr Hugh Croskery to settle some private debts and obligations including the settlement of a mortgage over one of the same homes that Mr Croskery agreed to transfer to George in settlement of those debts.

“It had nothing to do with the accounts at SSL or anything else.”

George will want his money and Hugh will have to find a way to give it to him.

Things went from bad to worse when a J$3 billion fraud (including US$12 million of Usain Bolt’s money went missing) was discovered, leading to the FSC and auditors swarming in only to find out SSL was mismanaged.

It’s a situation that Hugh Croskery will no doubt want to rectify. He will not want that stain on his name.

Croskery will also want to bequeath his children some of his assets most particularly his real estate holdings. All parents want to leave something for their children.

But not only that, it will be a source of sorrow to see both Mark and Sarah dragged into the SSL fraud imbroglio.

Mark has built a reputation as a financial operator now heading his own investment house. He is also a broadcaster, hosting his own show. The blowback from all this will impact his reputation – at least for the short term.

No father wants to see his children unduly suffer.

The fallout from all this must be unbearable for two young professionals who have promising careers – on a small island.

Both have moved to extricate themselves from this sad situation.

Hugh Croskery could never have imagined that he would see the day when he would have to face off in court with a good friend, neighbour and family member’s children through the management entity Coral Cove Management Limited (CCML).

For years his Discovery Bay property lay beside that of a close family friend so much so that the cove was impractical to separate – a metaphor for their bond.

Heidi Clarke and George Lopez may well have played with Hugh Croskery’s children on those long summer days before a new millennium.

A time of innocence, unaware that one day things would get ugly and they would do battle in court.

With Heidi and Bruce’s parents now passed, their claim is legitimate and Hugh Croskery cannot begrudge them. The Right of First Refusal (ROFR) here is not unreasonable.

Croskery would remember the good times and through the mist of time recall the children holidaying there, turning into fine and accomplished adults who made their parents proud. He would take an avuncular interest in their development and progress.

The prospect of facing them in court is something both he and their parents could never have fathomed.

Their birthright is under threat here and they have to protect it. Croskery will understand that having two children himself.

Come July 7, 2023, the Supreme Court will decide whether George Chai will have to wait until the CCML trial resolves the ROFR issue.

It is a quandary for Croskery.

Does he do the right thing by Usain Bolt and the others who were defrauded by his investment house?

Does he honour his debt obligations to his friend and partner George Chai who threw him a life line and is now looking for restitution?

Does he do all he can to see that his children’s reputation and prospects are not sullied? Can he leave them something for their future – perhaps a home?

Does he ensure Heidi and Bruce whose parents he was close with and whom he has known since they were children can go on enjoying the Discovery Bay residence unencumbered? Perhaps they can see it expanded.

To face them in a court must be unthinkable given that Hugh is in the autumn of his years.

He must be thinking about how he will be remembered and these entanglements will diminish his legacy.

What does he do?

What would you do?