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

General Sports

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

Well Played›
Jun 10, 202655:35

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Episode Notes

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

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How do I listen to this episode of Well Played?

"A Very Sportsish Well Played: Jordyn Woods’ Lucky Purse, Taylor Swift’s Stadium Wedding, and Prom in the NIL Era with Lily Shimbashi" is an episode of Well Played. Runtime 55 min. Published June 10, 2026. Hit play above to stream it here, or open the free Spot Sports app for background play and offline downloads.

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Quick FAQ

When was this episode published?
June 10, 2026.
How long is this episode?
55 min.
What podcast is this from?
Well Played. Browse the full back catalog on the show page.
What does this episode cover?
Well Played covers general sports. This episode runs on the show's regular cadence.

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