Australian Olympic Committee chief John Coates said a female staff member should "get out in the real world", because he was not running a "sheltered workshop", internal emails from the embattled organisation have revealed.
At the time, the young woman had cancer and had been treated for some months with chemotherapy.
Mr Coates knew this, according to the woman's then boss, former AOC chief executive Fiona de Jong, because he had "sent flowers to the hospital".
Ms de Jong said that, during her treatment the woman had "rarely missed a day of work".
The email exchange from January last year was included in a letter sent by Ms de Jong to the AOC board on Wednesday morning, ahead of a meeting to discuss a rash of recent stories about financial dealings and bullying allegations.
The exchange appears to have started after the woman drew attention to a drafting or typographical error in the AOC constitution that may need to be changed.
The chief financial officer, Sue O'Donnell, drew the issue to Mr Coates' attention, and he responded with a scathing email sent to six people, including much of the senior management of the AOC.
"After [the staff member's] stuff-ups in taking and loosing [sic] uniform measurements, she'd be wise to worry about improving her general performance in the Sports Department before venturing again into the area of drafting in which she has previously shown herself incapable," Mr Coates wrote.
To Ms O'Donnell, Mr Coates wrote: "Please try to be more discerning before worrying me with crap like this again."
The email trail shows the young woman immediately drafted her resignation letter, but Ms de Jong, her manager, tried to stop her from quitting. Ms de Jong wrote to Mr Coates at the time saying the woman was "most upset" by Mr Coates' email and "the public manner in which your opinions were expressed".
"This was particularly so as she values your opinion and holds you in high esteem."
Ms de Jong also wrote that the woman was the only one qualified to help select the team for the Rio Olympics that year.
Mr Coates' reply was blunt: "Do not hold back on accepting [the woman's] resignation on my account. We have spoken about her poor performance on a number of occasions."
The reference to a "sheltered workshop" came from Mr Coates in an email the following day, which also went to a number of senior managers.
"[The woman] is a solicitor, hardly a junior member of staff. If she's offended it's probably time for her to get out in the real world. Ours is not a sheltered workshop. Kind regards, John."
The woman, like many other who have made allegations of bullying inside the AOC, resigned shortly afterwards.
A sheltered workshop is a place where people with disabilities work separately from a fully abled workforce. It's also used colloquially to disparage the work and abilities of a fully abled employee.
The AOC board is meeting later today after several rebel board members called for it to look into recent allegations.
Mr Coates faces a May 6 fight for re-election against former Hockeyroo Danni Roche, but has been plagued by allegations of a bullying culture inside the organisation.
Mr Coates wrote on Monday in a letter to the sports federations which will vote in the election that: "There is no place for bullying and I reject the suggestion of a culture of 'bullying' or a lack of action in response to allegations of it."
That statement prompted a furious letter sent by Ms de Jong to the board early on Wednesday.
In the letter, Ms de Jong outlines 12 different complaints of bullying, formal or informal, between 2004 and 2016. Some involved Mr Coates' media director and right hand man, Mike Tancred, but other, unnamed staff members were also the subject of complaints, she wrote.
"I'm not sure how many complaints are required in order for an organisation to be characterised as having a culture of bullying, but, on any analysis it is untrue for my complaint to be characterised as an isolated incident," Ms de Jong wrote.
She also complained to Mr Coates about "delays" when dealing with her own complaint against Mr Tancred, which was lodged in December.
Mr Coates wrote on Monday the board needed to decide on how to deal with her complaint.
But Ms de Jong responded in her letter to the board: "It is difficult to accept that 'due' process has been followed when, in fact, four months after the filing of a complaint no process has been determined, let alone followed 'duly' or otherwise."
Mr Coates has been approached for a response. Mr Tancred has previously denied bullying other AOC staff.
