He entered Ontario's psychiatric system nearly 34 years ago as Vance Egglestone, whose criminal history involved choking and raping women in bars.

Today he is known as Shauna Taylor and aspires to a feminine life in a maximum-security wing of the Penetanguishene Mental Health Centre.

He wears makeup and women's clothing, but isn't much for orchids.

Taylor, 53, wants to undergo a procedure known as a double orchidectomy, the surgical removal of both testicles, to complete his transition to womanhood.

(The word "orchid" comes from the Greek word "orkhis," or testicle, which the plant's roots resemble.)

A central issue in the case, which comes before the Ontario Court of Appeal Wednesday, is whether Ontario's Ministry of the Attorney General should pick up the cost of a medical assessment to determine whether Taylor should have the surgery.

At a hearing in July 2007, the Ontario Review Board, which has jurisdiction over about 1,000 people found unfit to stand trial or not criminally responsible on account of mental disorder, was told by forensic psychiatrist Ron Langevin that Taylor suffers from "gender identity disorder."

Langevin, who recommended the surgery, believes it would improve Taylor's sense of well-being and reduce her risk of reoffending if released back into the community.

(Staff at the institution refer to Taylor using a feminine pronoun.)

But board members have been skeptical because some clinicians and consultants at the hospital suspect Taylor is faking the disorder to get moved to a less restrictive institution.

Since 1995, every time she has tried to get out of Penetanguishene's Oak Ridge division, she has failed.

Given Taylor's history of deceit, the board found in 2007 she can't be trusted to be honest about her alleged condition.

So the board ordered Taylor to be assessed by the gender identity clinic at the Centre for Addiction and Mental Health in Toronto, with costs to be borne by the attorney general's ministry.

The ministry appealed and a Superior Court judge overturned the decision, saying the board exceeded its jurisdiction.

The next year, at her annual detention review hearing, Taylor again pushed for the surgery.

The board ordered her to undergo a psychiatric assessment by Dr. Paul Federoff at the Royal Ottawa Mental Health Centre, with costs to be paid by the attorney general.

The attorney general's ministry, on appeal, got the costs order overturned.

In legal terms, the case is not only about who pays for the assessment, but a dispute about the scope of the Ontario Review Board's power, which will have implications for future hearings.

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And if Taylor gets the surgery, it could affect whether she ever gets out.

Both Langevin, who believes Taylor has gender identity disorder, and Dr. Stephen Hucker, a forensic psychiatrist who will only go as far as saying it "may" be a possibility, agreed that after an orchidectomy was performed, Taylor's risk to the public would have to be reassessed.

In 1998, the board noted, Taylor was heard saying that if her testosterone levels dropped to zero, the hospital would have no reason to hold her.