Off the Cuff

Photo by Cathy Pinsky
Editorial assistance by Madeline Berg
Checkerboard hand-painted by Robin Weiss

Off to the Races

Horse and jockey in 14-karat gold (I. Reiss Collection) $1,800
LANDSBERG JEWELERS
Rye Brook
(914) 510-8920

Good Times Past

Authenticated mechanical watch movement from early- to mid-20th century set in sterling silver (Tokens & Icons) $140
R&M WOODROW JEWELERS
Rye (914) 967-0464

Jolly Rogers Jewelry

Skull-and-crossbones in sterling silver with enamel (Deakin and Francis) $325
WILSON & SON JEWELERS
Mount Kisco (914) 241-4500
Scarsdale (914) 723-0327

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Play Ball

Piece of actual MLB-certified baseball used in previous game
(Tokens & Icons) $140
R&M WOODROW JEWELERS
Rye (914) 967-0464

Cocktail Cufflinks

Sterling-silver martini glass with peridot olive (Robin Rotenier) $295
DESIRES BY MIKOLAY
Chappaqua
(914) 238-2223