John, Jack, Stevie, and Sam kick off the week by breaking down the biggest headlines in tennis.

The boys recap the big results from Washington D.C., discuss Venus Williams’ return to the court, and preview the tour’s upcoming stops in Canada.

The crew start an important debate, what are the ugliest swings in tennis history? And reveal what insurance looks like for pro tennis players.

Plus, they tease an exciting special guest joining Friday’s episode…

00:00 Intro

00:50 Weekend Recap

01:12 Washington DC Event Highlights

03:13 Men's Final Analysis: Thrills and Heartbreaks

05:34 First Titles and Player Reflections

10:10 Ben Shelton's Performance and Potential

16:23 Venus Williams' Comeback and Women's Highlights

21:29 Other Tournament Results and Cheap Points Debate

23:04 Insurance Talk and Retirement Benefits

23:42 Retirement Insurance Options

24:39 The Hassles of Dental Insurance

26:12 Booking Flights and Celebrity Tasks

27:27 Toronto vs. Montreal Tournaments

32:51 Debating Ugly Tennis Strokes

38:07 Heated Argument and Final Thoughts