When Gene Demby and I were planning this week’s sports discussion, we didn’t say, “We should sit down Monday to discuss the U.S. Open.” We’d planned to discuss Serena Williams, the most dominant player in women’s tennis, who was expected to complete a rare Grand Slam in Saturday’s final. (To win a Grand Slam, a player must win the Australian Open, the French Open, Wimbledon and the U.S. Open in a single calendar year. The last woman to accomplish the feat was Steffi Graf in 1988, though Williams had technically won all four majors in a row leading up to this year’s U.S. Open.)

But Williams ended up losing in a shocking upset Friday, falling to unranked Italian Roberta Vinci. This set up an all-Italian final match between Vinci and fellow underdog Flavia Pennetta, who’d shocked another dominant player, the No. 2-ranked Simona Halep, en route to the final. Suddenly, what looked like a history-making coronation was a battle of little-known underdogs — two women who’d known each other since childhood, and were at the tail-end of their careers. (Pennetta announced her retirement shortly after winning.)

So instead of talking about Serena Williams for an entire segment, Gene and I examine the double-edged sword that is rooting for an underdog, lament sports announcers’ insistence upon psychoanalyzing athletes, and try to unpack what makes us root for and against dynasties in sports. Along the way, we take on the myth of athletes winning because they believe in themselves — when Vinci was asked when she realized she might actually beat Williams, Vinci replied, “Never” — and even spend a minute or two acknowledging Sunday’s gripping men’s final between top-ranked powerhouses Novak Djokovic and Roger Federer.