This endlessly charming original illustration by Maurice Sendak, created in watercolor and ink as a December cover of a 1976 issue of Rolling Stone, depicts Sendak’s cheerfully game Wild Thing being decorated like a Christmas tree by a couple of human kids and a pup. Sendak’s lifelong obsession with children’s id-based adventures, sibling dynamics and the freedom we discover in unchecked imagination is epitomized in this picture. It is a wonderfully balanced composition that keeps the eye moving.

Maurice Sendak A Wild Thing Christmas, King of All the Wild Things

Rolling Stone cover, December 30, 1976
Watercolor and ink on paper
Estimate: $120,000-$180,000

Auction: November 4

One of three related bowls that were made by Gorham Mfg. Co. in 1884-1885, this partial gilt silver punch bowl-form yachting trophy was a special commission and features a multitude of elaborate sea motifs inspired by Japanese art, including a finely chased design of an artist with palette and brushes riding a dragon alongside serpents and fish, as well as handles in the form of dragon heads. The bowl, which comes out of the American Aesthetic Movement, rests on a circular ring of intertwined snakes, and its undulating rim features silver seashells, sand and seaweed.

A Gorham Mfg. Co. Partial Gilt Silver Punch Bowl-Form Yachting Trophy: Hera

Providence, Rhode Island, 1884
Estimate: $100,000-$150,000
Auction: November 15

Given a status of “Unique” in Campiglia and Wells’ The Official U.S. Casino Chip Price Guide, this rare and desirable poker chip is the only known surviving $100 chip from the Frontier Hotel dating from its opening in 1967 under new ownership of business mogul Howard Hughes. The chip easily stands on edge with no signs of use or wear. Once purchased, rare chips such as this one tend to remain embedded in top collections for a lifetime, so this is likely to be collectors’ only public opportunity to add this piece to their collection.

1st Issue, Rated “Unique,” $100 Frontier Hotel Poker Chip

Auction: December 3