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   Chris Black Lives the Dream at Wimbledon
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   Two years after a rainy heartbreaker on the court.
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                   <p style="margin:0;font-size:15px;mso-line-height-alt:22.5px">
                    <span style="word-break: break-word; font-size: 15px;">
                     After celebrating America’s 250th birthday in
                     <a style="text-decoration: underline; color: #000000;">
                      Miami
                     </a>
                     , one of America’s best and most humid cities, I pulled a travel move that, from experience, is either a perfectly calculated maneuver or a stunning failure. We returned, sun-kissed and full of stone crab, to LaGuardia at 9 AM on Monday. I had most of the rainy day to complete my errands and menial tasks, repack, and be back at JFK,
                     <a style="text-decoration: underline; color: #000000;">
                      New York
                     </a>
                     ’s worst
                     <a style="text-decoration: underline; color: #000000;">
                      airport
                     </a>
                     , by 7:30 PM for a night flight to
                     <a style="text-decoration: underline; color: #000000;">
                      London
                     </a>
                     .
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                   </p>
                   <p style="margin:0;font-size:15px;mso-line-height-alt:22.5px">
                    <span style="word-break: break-word; font-size: 15px;">
                     After a mediocre four hours of interrupted sleep, I arrived at Heathrow, was greeted by my driver, and was whisked away in a new black Range Rover with the Wimbledon logo on the doors. I was off to Estelle Manor, a hotel and members' club on the edge of the Cotswolds in Oxfordshire, with a pristine pool, incredible landscaping, and a gym that was a little
                     <em>
                      too
                     </em>
                     good. I arrived relatively depleted, but after a post-travel pump at the aforementioned gym and a shower, I was a new man and able to grab a poolside seat, sandwiched between pasty Brits in Gymshark shorts who were sucking down afternoon Aperol Spritzes and pints like we were in
                     <a style="text-decoration: underline; color: #000000;">
                      Ibiza
                     </a>
                     .
                    </span>
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                   <p style="margin:0;font-size:15px;mso-line-height-alt:18px">
                   </p>
                   <p style="margin:0;font-size:15px;mso-line-height-alt:22.5px">
                    <span style="word-break: break-word; font-size: 15px;">
                     I had to be up early for a trip to
                     <a style="text-decoration: underline; color: #000000;">
                      Jaguar
                     </a>
                     Land Rover headquarters in Gaydon, Warwickshire, a city with a name so British I feel wrong saying it. My love of cars is non-existent; I’ve never seen an episode of
                     <em>
                      Top Gear
                     </em>
                     or
                     <em>
                      The Grand Tour
                     </em>
                     , but I am always happy to hear dedicated experts wax poetic about their passions. This shit was no joke; getting in felt like a visit to the White House. I even had to put my cellphone in a locker. Once we hit the design studio, a litany of high-level employees walked us through the ins and outs of the whole operation. My takeaway was that innovating in the auto space in 2026 takes very smart people and a lot of time; this shit is hard. I maintain that cars should only be offered in black, white, and silver, but I think I am in the minority on that opinion.
                    </span>
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                   </p>
                   <p style="margin:0;font-size:15px;mso-line-height-alt:22.5px">
                    <span style="word-break: break-word; font-size: 15px;">
                     We left the factory, climbed in our fleet of Chelsea tractors, and made a beeline for London proper. We checked in at The Chancery Rosewood in Mayfair, which is situated in a former U.S. Embassy building. (It was nice to see that they kept the giant eagle affixed to the roof, a warm welcome that felt personal.) The real point of this journey was to attend the women’s semi-final match at Wimbledon, something I have wanted to do since I was a child. Two years ago, I realized that we would be in London during the tournament, and thanks to some friends in the tennis business, I secured passes only to sit in the dining area for seven hours as God pissed down on us. We left with a nice big-boy logo umbrella but didn’t see any real action. The taste of strawberries and cream is the only good memory I have from that failed attempt. I was looking for redemption.
                    </span>
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                   </p>
                   <p style="margin:0;font-size:15px;mso-line-height-alt:22.5px">
                    <span style="word-break: break-word; font-size: 15px;">
                     Range Rover is a presenting sponsor of the tournament, so after hitting the hospitality suite for some ice-cold Evian and a surprisingly entertaining breakdown of the match between Coco Gauff and Karolina Muchová from Annabel Croft, a former British professional player and BBC talking head, I was off to my seat, which was mercifully located just inside the shaded stands on centre court. I wore a suit because it felt like the right thing to do, but with the heat and the much-talked-about lack of air conditioning, I felt overdressed. After the warm-up, my blue J. Mueser double-breasted jacket was folded in my lap, creating an unfortunate blanket-like situation. I was able to thug it out for a fantastic three-set match that ended in Gauff choking badly in a tiebreak.
                    </span>
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                   </p>
                   <p style="margin:0;font-size:15px;mso-line-height-alt:22.5px">
                    <span style="word-break: break-word; font-size: 15px;">
                     After the main event, I wandered the grounds and did some bench-sitting and people-watching. The ballot ticketing system they employ ensures anyone can get a ticket, and you can feel it. It’s not just rich people who can overspend on StubHub; it’s people who really want to be there because it’s a rich part of British culture. I didn’t see anyone with their camera suction-cupped to a pole, twirling around to film their Wimbledon outfit. After taking in some wheelchair matches and investigating the cavernous merchandise store, I was able to resist buying a cartoon plush strawberry bagcharm or a custom monogrammed Ralph Lauren towel. I decided to buy the small, more portable logo umbrella, a nice and useful reminder that the second time can be the charm.
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                        Related reading from
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                         The 76 Best Menswear Moments of Wimbledon 2026
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                          Andrew Garfield Won Wimbledon With a Can’t-Fail Summer Style Move
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                          Roger Federer's Rolex, Serena Williams's Comeback AP, and More of the Best Watches at Wimbledon
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