Simon had served with the CAF for approximately nine and a half years from June 1980 to 23 October 1989, when he was medically discharged from the CAF for being HIV-positive. At the time of his discharge, Simon operated large weapons and electronic surveillance equipment on a variety of warships.
In 1986, Simon discovered that he was HIV-positive. From May 1986 until November 1987 the progression of his disease was uneventful, yet in the fall of 1986 he was removed from his final qualifying course to become a full Master Corporal and at the same time his security clearance was downgraded. It was only as a result of a tribunal hearing in 1992 that he discovered that this removal was a result of his sexual orientation and not his HIV-positive status.
In late October and during November of 1987, he began developing symptoms of HIV, including night sweats and a reduced T-cell count. In March 1988, military doctors conducted a "paper" medical assessment, at which time his medical category was downgraded. As a result, in November 1988 the CAF decided to release Simon, effective 23 October 1989.
In June 1993, after a lengthy inquiry, a human rights tribunal upheld Simon's complaint. It found that the CAF had an obligation to properly assess the risks involved in retaining Simon, including the risks of his going to sea, far from hospital facilities. The military was also required to consider various options other than outright release. These included, for example, using medical assistants on ships in conjunction with military doctors to assist Simon, as well as transferring him to another military occupation.
The Tribunal held that the military had discriminated against Simon as a result of his disability. It held that the military failed in its legal duty to accommodate Simon's disability and to individually assess his capabilities in the context of the risk that he potentially posed to himself and others. It also held that the increased risk posed by retaining a disabled person in the Forces had to be more than a minimal risk before the Forces could justify outright dismissal.
As part of its award, the Tribunal ordered the military to pay back wages as well as some future amounts that would have been owing to Simon had he been retained in the CAF. The Tribunal awarded the maximum amount possible for hurt feelings and its total compensation totalled more than $160,000. It also awarded his legal and actuarial expenses.
The military appealed this decision. It also applied to the Federal Court for an interim order allowing it to withhold payment to Simon pending the outcome of the appeal. In September 1993, the Federal Court refused to grant the interim order, saying that Simon "should be allowed to live his remaining days in dignity." In March 1994, the Federal Court dismissed the military's appeal in its entirety.