Two letters of a 1923 law will determine whether the YMCA of Toronto has to pay the taxes on four valuable properties it leases in the centre of the city.

It all depends on the meaning of the word “of.”

In May, the charity applied for an exemption from municipal property taxes for four properties. The city successfully opposed the move, arguing that because the YMCA leases from management companies and does not own the properties, it should be required to pay taxes.

That one small preposition is responsible for a 3,242-word judicial deconstruction and a case now before the Ontario Court of Appeal that will affect decisions in at least five other Ontario towns and cities: Mississauga, Markham, Uxbridge, Bolton and Port Perry.

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The 1923 provincial act that established the YMCA in Toronto exempts the organization from taxes on any “buildings, lands, equipment and undertaking of the said association,” as long as they are used for YMCA purposes.

The four leased properties at issue are not buildings, equipment or undertakings, Superior Court Justice Paul Perell concluded in his ruling in June.

They are “land,” at least for property law purposes, he wrote. But if the YMCA only leases these properties, and doesn’t own them, are they still tax-exempt as “land of the YMCA?”

Posing this question in his decision, Perell takes a grammatical detour several paragraphs long, exploring the use of the word “of” to indicate possession.

“And here it may be noted that prepositional phrases using ‘of’ are frequently used as substitute for the possessive ‘s’. One of the fundamental uses of ‘of’ is to indicate the relationship of ownership,” he wrote. “Thus, ‘the woman’s car’ becomes ‘the car of the woman.’”

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A person may use a property he or she leases, but the property still belongs to someone else, Perell concluded. So although the YMCA uses those four properties — as a youth shelter, administrative office, child-care centre and site of programs for at-risk young men — they are not technically the YMCA’s land or land “of” the YMCA, he ruled. Therefore the YMCA cannot claim a tax exemption.

The YMCA is appealing the ruling.