It might take a while to win big during Monterey Car Week. You might spend years looking for a car that might turn heads. You can spend a small fortune building it and getting it restored. When it\u2019s finally ready, you haul it—carefully—to California, and park it on the grass, or the paddock, and polish the Borrani wire-spoke wheels with a microfiber towel in between track sessions. And if you\u2019re lucky, you\u2019ll get a trophy—and you\u2019ll also get a timepiece.Rolex is the official timekeeper at three of the most prestigious events during Monterey\u2019s famed Car Week: The Quail Motorsports Gathering, the Rolex Monterey Motorsports Reunion, and the big show on Sunday, the Pebble Beach Concours d\u2019Elegance. Each event winner is awarded a brand-new Rolex in its own felt-lined presentation box, engraved on the caseback with the stunning accomplishment: Winner, Spirit of Monterey Award. Winner, Best of Show. It\u2019s not just any watch. It\u2019s not just any Rolex, either: With the collectability and inherent specialness of a luxury Swiss timepiece, something so bestowed takes on much more significance. We wonder: What do you do with something this special? This personal? Do you wear it every day, or do you tuck it away? So we asked the fortunate few from all three events what they do with their prizes. Meet the WinnersThe Quail Motorsports Gathering, 2016Best In Show: 1953 Ferrari 375 MM Pinin Farina SpyderOwner: Andreas Mohringer, AustriaAustrian collector and pharmaceutical entrepreneur Andreas Mohringer won the 2016 Quail Motorsports Gathering with a Ferrari race car that was wonderfully rough around the edges. He had found the 1953 Ferrari 375 MM Pinin Farina Spider in a barn, where it had sat in storage for the past four decades; upon taking it home, he had it mechanically sorted but still left it as original as possible. It\u2019s lucky he did. Originally, this 375 MM was just one of nine ever built, in 1953. A year later, Phil Hill won the Sebring 24 Hours in it. Two decades of racing success followed before it went into retirement, but clearly Mohringer appreciated all of the imperfections and scratches, echoes of hard-fought victories, enough to leave them alone. The judges thought so too. For his Best In Show pick Mohringer took home a Rolex Oyster Perpetual Cosmograph Daytona. This is the first time the Quail has ever granted its highest honor to an unrestored car. \u201cMarks of time,\u201d the judges will call it, and it would be a shame to wipe away all of that history, all of those signifiers of greatness. Rolex Monterey Motorsports Reunion, 2015Spirit of Monterey Award: 1917 Hall-Scott \u201cThe Four\u201d A-7AOwner: Dick DeLuna, Woodside, CaliforniaIf the Rolex Monterey Motorsports Reunion\u2019s vaunted Spirit of Monterey Award is supposed to \u201cexemplify the spirit of Monterey,\u201d then that spirit is loud, shiny, and fast. In 2015, Dick DeLuna of Woodside, California brought to the hallowed grounds of Mazda Raceway Laguna Seca a great hulking beast from the Great War, powered by a 9.9-liter four-cylinder engine ripped from an airplane, with pistons that are practically the width of telephone poles. Its shiny hand-formed aluminum bodywork holds a leering black grille upfront and a torpedo tail in back. Its exhaust is five inches in diameter, sounding like an avenging angel when it storms down Turn 10. In the Pre-1940 Sports Racing and Touring Cars class, DeLuna may have finished tenth, but he stole the show—and took home a Rolex Oyster Perpetual Cosmograph Daytona, 18k yellow gold and stainless steel, alongside his trophy.Pebble Beach Concours d\u2019Elegance, 2016Best Of Show: 1936 Lancia Astura Pinin Farina CabrioletOwner: Richard Mattei, Paradise Valley, ArizonaLast year, Richard Mattei entered the Pebble Beach Concours d\u2019Elegance for the first time, hoping to place third, at least. Instead, he won Best Of Show. And in one afternoon, six years of restoration work for his 1936 Lancia Astura Pinin Farina Cabriolet—one of seven coachbuilt examples, a car once dragged from a British yard for \u00a315—paid off. It also helps that former owner Eric Clapton once called this exact Lancia \u201cthe most fun I\u2019ve had off stage and out of bed.\u201dAt his home outside Scottsdale, Mattei collects Alfa Romeos; with an appreciation for Italian style and craftsmanship, he ensured that the Lancia marque took its first victory at Pebble Beach. A trophy for a past Italian great, and a Rolex Oyster Perpetual Datejust in steel and Everose gold for the owner\u2019s wrist.Q&AR&T: Has owning the Rolex sparked a greater interest in timepiece collecting?Mohringer: Not particularly, as I already own a few vintage watches, which also means that the Daytona got a new and appreciative home.DeLuna: I have been collecting watches for years, bought my first stainless Daytona 12 years ago.Mattei: I have several timepieces and have enjoyed adding the Rolex award to my collection. R&T: 1994's 24 Hours of Daytona winner Steve Millen was once spotted working on a race car while wearing his Daytona. Do you wear yours, or do you keep it under lock and key?Mohringer: Both, so to speak. The Daytona is shared with and worn by my wife. We both believe that the Daytona suits both ladies and gentleman equally well—not always the case with the same watch.DeLuna: I wear mine three to four times a week.R&T: What does the watch represent to you?Mohringer: A symbol for craftmanship. Tradition, recognition, and long-lasting qualities.DeLuna: It represents a humbling honor to receive the Rolex Monterey Motorsports Reunion, ''The Spirit of Monterey,'' after 30- years of racing. To me, it\u2019s the best of the Rolexes—elegant, understated, and timeless in design.Mattei: This watch and its style perfectly complements the theme of the Pebble Beach Concours—\u201celegance." R&T: What do people say when they see it?DeLuna: Family says it's the best of the best—it's a Rolex. Friends say, "I have one just like yours." I'll respond, "Not exactly—take it off and look on the very special engraving from Rolex." Only a few have this. Makes me very proud. Thanks, Rolex.Mattei: The watch attracts attention when I wear it because of its elegance. It always leads to a discussion about the August event at Pebble.R&T: What are some memorable encounters you\u2019ve had while showing off your timepiece? DeLuna: My local jeweler, Kerns of Burlingame, a Rolex dealer, could not believe me until I brought it in with its special box and all.R&T: Do you see your Rolex as a family heirloom?DeLuna: We have five boys and one girl—you figure it out. It is one of the personal items treasured by all.Mattei: It will be handed down to my son.R&T: What do you enjoy most about the timepiece?DeLuna: It is immediately recognized without being overbearing. The fraternity of car people and racers appreciate its timeless design and worldwide recognition.Mattei: The watch will always bring me back to the 2016 event. With the engraving on the reverse it stands as a special item for me.