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

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