A Very Sportsish Well Played: Jordyn Woods’ Lucky Purse, Taylor Swift’s Stadium Wedding, and Prom in the NIL Era with Lily Shimbashi

While Caroline is honeymooning in the Dolomites, Lily Shimbashi, founder of Sportsish, joins us to break down the most important news in sports and pop culture. Madison Square Garden is on our minds this week – and it’s not just because the Knicks lost at home. Rumor has it that Taylor Swift’s wedding will take place at the iconic New York City arena on July 3. Are we buying it? No. What’s are people *actually* buying when it comes to the pop star? The literal chair she sat on during the Cav’s Game 3 of the Eastern Conference Finals. We hate it here too. In this episode of Well Played, we also cover: Serena Williams’ return to the grass – and why “mom brain” got the best of her  Breaking down the World Cup stages, and which teams to watch  Kim Kardashian re-entering the WAG world, thanks to Lewis Hamilton  The Hockey Canada 5, and why Lily thinks it’s been a hard Stanley Cup for female fans  Send Its: Serena v. mom brain: https://www.reddit.com/r/tennis/comments/1u05nx8/serena_forgetting_where_she_has_to_serve_and_it/?solution=6fade7a9855ac5106fade7a9855ac510&js_challenge=1&token=7afd7253fec22262ff1c52b1703fe9ecba37f2c27935c160fc00b397029b5e0f&jsc_orig_r=  Does Trey Jemison know he’s getting married?: https://www.instagram.com/p/DNEl36Nukmi/?img_index=1  Kim K re-enters her WAGdom: https://people.com/kim-kardashian-wears-low-back-dress-lewis-hamilton-f1-monaco-11993179 Plus: check out The Athletic's FIFA World Cup group stage breakdown: https://www.nytimes.com/athletic/interactive/world-cup-2026-group-stage-draw-live/ Follow Sportsish on Instagram: @sportsish  Subscribe to Sportsish on Substack: https://sportsish.substack.com/ Follow Well Played on Instagram: @wellplayedbytheskimm  Follow Blake on Instagram: @blaakkkke Learn more about your ad choices. Visit megaphone.fm/adchoices