Chris Black Lives the Dream at Wimbledon

This is an edition of the newsletter Pulling Weeds With Chris Black, in which the columnist weighs in on hot topics in culture. Sign up here to get it in your inbox every Thursday.After celebrating America’s 250th birthday in Miami, 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, New York’s worst airport, by 7:30 PM for a night flight to London.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 too 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 Ibiza.I had to be up early for a trip to Jaguar 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 Top Gear or The Grand Tour, 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.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.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.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.