Hearts boss Gary Locke admits waving goodbye to 14 staff members made redundant by the stricken club's administrators was more painful than two devastating knee injuries.
The former Tynecastle skipper ruptured knee ligaments in the 1996 Scottish Cup final his side lost 5-1 to Rangers.
The same injury sustained in March 1998 denied him the chance to gain revenge on the Ibrox side as he missed their 2-1 victory in the 1998 final.
But the 38-year-old says the scars of two career-saving operations pale in comparison to the human cost of the Jambos' descent into administration.
BDO is now in charge of the club's operations but its first action was to lay off 14 of the club's backroom workforce.
Locke told Press Association Sport: "The last few days have been as bad as I've had in football.
"I've had a couple of cruciate injuries and they were devastating. But they just don't compare to anything I experienced on Thursday.
"To see so many great people lose their jobs was heartbreaking."
Hearts owe £25million to Lithuanian companies UBIG and Ukio Bankas.
Both firms were formerly controlled by ex-Hearts owner Vladimir Romanov but UBIG is now waiting to be put into administration after its assets were frozen, while Ukio Bankas will soon be liquidated after a Kaunas court declared it insolvent.
The bank, however, has a floating charge on Tynecastle and other club assets as security for the £15million it is due, leading to fears that the stadium could be sold off to repay its own debts.
It was the threat of court action over a partially-paid £100,000 tax bill, however, that sparked the decision to place the Edinburgh outfit into administration.
Locke was in Turkey on a family holiday when news broke of the club's perilous state but the manager admits he had no idea things had got so bad.
He said: "I was away on holiday and didn't see this coming. During the summer I've been trying to get things moving in terms of building a team that I thought could challenge at the right end of the table.
"But the last few days of my holiday I was being made aware constantly of what was going on by John Murray, the director of football.
"To come back to this has been very difficult. I was here on Thursday and saw everything unfolding.
"I met the administrators and it was a difficult day. I've certainly not had much sleep since.
"My thoughts are with the 14 people that have lost their jobs. They are great people. A few of them have been here a number of years and you get close to them."