Post-Wimbledon Mega Mailbag (2025)

On the post-Wimbledon 2025 Mega Mailbag, Gill Gross responds to your comments, including: who will win the Career Grand Slam first between Carlos Alcaraz and Jannik Sinner, is there any precedent of Grigor Dimitrov’s potentially history-altering injury, is Sinner already good enough to win Roland Garros next year, why is tennis discourse so tribalistic, why were there so many upsets at Wimbledon, what improvements did Iga Swiatek make to win Wimbledon, where does Sinner’s ballstriking rank all-time, is Darren Cahill going to retire, is Novak Djokovic going after Federer and Connors title records, are Jack Draper and Ben Shelton Sincaraz’s biggest threats, a Fabio Fognini retirement tribute, Nick Kyrgios’s analysis on Amanda Anisimova, Roddick’s take that Sinner slides too much, coverage of women’s tennis on the show, Agassi’s comments on Fritz’s return and more. 0:00 Intro 1:40 Career Grand Slam 5:11 Dimitrov’s Injury 10:50 Re-Analyzing RG Final 13:57 Tennis Tribalism Discourse 21:58 So Many Upsets 25:15 Swiatek Improvements 31:40 Sinner Ballstriking All-Time 34:30 Cahill Retirement 37:33 Djokovic Titles Count 40:49 Shelton & Draper Contendership 45:35 Djokovic Current Mental 49:55 SIncaraz Closeness 52:43 Fognini Tribute 57:02 Fritz or Zverev Slam 59:48 Sinner’s Last 52 Weeks 1:02:55 Kyrgios on Anisimova 1:05:05 Chasing Sincaraz Mentality 1:09:55 Sabalenka Slam Issues 1:12:40 Sincaraz H2H 1:15:40 Sinner Grass sliding 1:18:13 Learning From Losing 1:21:30 Women’s Coverage 1:24:20 Slow 2nd Serves 1:26:20 Agassi On Fritz 1:30:04 Sinner Emotion IG: https://www.instagram.com/gillgross_/ TikTok: https://www.tiktok.com/@gill.gross 24/7 Tennis Community on Discord: https://discord.gg/wW3WPqFTFJ Twitter/X: https://twitter.com/Gill_Gross The Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribe Become a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/join Evans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffee IG: https://www.instagram.com/gillgross_/TikTok: https://www.tiktok.com/@gill.gross24/7 Tennis Community on Tribe: https://tribechat.com/gillTwitter/X: https://twitter.com/Gill_GrossThe Draw newsletter, your one-stop-shop for the best tennis content on the internet every week: https://www.thedraw.tennis/subscribeBecome a member to support the channel: https://www.youtube.com/channel/UCvERpLl9dXH09fuNdbyiLQQ/joinEvans Brothers Coffee Roasters, the Official Coffee Of Monday Match Analysis... use code GILLGROSS25 for 25% off your first order: https://evansbrotherscoffee.com/collections/coffeeAUDIO PODCAST FEEDSSpotify: https://open.spotify.com/show/5c3VXnLDVVgLfZuGk3yxIF?si=AQy9oRlZTACoGr5XS3s_ygItunes: https://itunes.apple.com/us/podcast/monday-match-analysis/id1432259450?mt=2 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.