Francesco Pellizzi, 73, said his mother bought the 27-by-20-inch drawing for $8,800 in 1988 and gave it to him as a Christmas gift.
Pellizzi realized it went missing from a file drawer in which he kept it and notified police in 2000, said his lawyer, Peter Stern.
Pellizzi didn't see the drawing again until it showed up this year in a Christie's catalogue, the New York Daily News reported Saturday.
Pellizzi filed a lawsuit last month in Manhattan Supreme Court, asking for $520,000 of the proceeds from the auction.
The seller of the drawing, Chicago lawyer David Ruttenberg, said he and his art dealer, Jennifer Vorbach, bought the drawing in 2012 and researched its ownership as far back as a decade ago.
"It changed hands a number of times, but Vorbach and Ruttenberg are not able to trace it back to anyone who obtained it from Mr. Pellizzi," said Stern.
Ruttenberg and Vorbach's lawyer, Thomas Stauber, said Pellizzi's claim is "belated" and he expects the case to be dismissed.
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