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

IG: https://www.instagram.com/gillgross_/

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