
Yesterday, the personal belongings of legendary singer-songwriter Gordon Lightfoot were sold off one by one in a six-hour live auction by A. H. Wilkens Auctions and Appraisals.

Among the objects for sale were a guitar strap made from real snakeskin, a taxidermied tiger rug ($4,404), a bound 59-page report on the SS Edmund Fitzgerald titled “What Really Did Happen” (unsold) and the red leather jacket Lightfoot wore on the cover of his album Endless Wire ($2,328).
While there were plenty of the usual items one would find at a celebrity auction—books, records, furniture, instruments—the closeout contained a borderline alarming number of deeply personal effects, including several of Lightfoot’s old high school yearbooks (which sold for $276) and childhood report cards ($432). One lot, containing a baby book issued by the Orillia hospital at the time of Lightfoot’s birth and a lock of the singer’s baby hair, was withdrawn at the request of the family (fair enough). Another lot containing autographed promotional photos from earlier in his career was partially withdrawn due to copyright concerns. (The two photos still sold for $456.)

While the auction may be over, we perused over 30 pages of items up for grabs and learned a few things in the process.

The auction contained several lots of leather boots worn by Lightfoot onstage, including a pointy pair of cream-coloured Cuban heel ankle boots made in Italy (size nine) and red leather cowboy boots by the brand Justin (size 8.5). Light foot, indeed.

One lot contained a handwritten note from Bob Dylan on Chartmaker Studios letterhead ($2,082), which read, “If you need me, Bob Dylan” followed by the singer’s phone number: 457-6823. (It’s probably changed since then.)

Why else would Lightfoot have owned this vintage Blue Jays jersey emblazoned with the number nine? We’re not exactly sure which player the jersey is repping, but our money is on Darrin Fletcher.

Lightfoot definitely preferred the mid-century modern aesthetic, if several lots in the auction are any indication. His office desk ($4,650) was this incredibly sleek teak number. He also had a great love for overstuffed brown leather pieces, including a sofa ($1,044) and an armchair with a matching ottoman. A futuristic egg-like “karate” chair designed by Michel Cadestin ($1,956) also displays refined modernist taste. (The strange rhino-shaped leather ottoman by Abercrombie and Fitch, not so much.)

While Lightfoot was obviously fascinated by the SS Edmund Fitzgerald shipwreck—to the point where he wrote one of his most beloved songs about it—the auction suggests that his interest went beyond mere background research. It contained multiple lots of SS Edmund Fitzgerald–related paraphernalia, including marine casualty reports ($732), coast guard manuscripts ($396), a funeral ceremony pamphlet in memory of the crew ($396), multiple art pieces ($732 and $396) and an unproduced movie script about the shipwreck (unsold). Compare that to a single photograph of Lightfoot in front of Carefree Highway ($918).
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A vintage golf bag bearing Lightfoot’s name and filled with an admirable selection of putters and drivers suggests a man who loved to get out on the green.

One lot (unsold) featured a horde of yellowed press clippings collected by Lightfoot himself, including a full copy of a Maclean’s magazine from 1978.

When Darwin, the “stylish but illegal” monkey, was found wandering alone inside the North York IKEA parking lot in 2012, observers rightfully took note of his impressive shearling coat. As it turns out, Gordon Lightfoot owned a vintage brown shearling coat ($456) almost identical to that of the IKEA monkey, drawing an interesting parallel between two of the country’s most beloved icons.
Isabel B. Slone is a fashion and culture journalist living in Toronto. She writes for Toronto Life, the New York Times, the Guardian, the Wall Street Journal, Architectural Digest and more. She has a master’s degree in journalism from Columbia Journalism School.