Connors, who won 109 titles including eight singles majors, turned 39 during the 1991 US Open, which he entered as a wild card due to a ranking of No. 174. Embraced by the sensation-loving New York crowd, he powered to the semifinals—working the fans with his bombastic antics, flabbergasting opponents, and entwining a global audience in his bid to record a rare win over father time.
But Connors wasn’t the only hero to leave the stage with a mic drop. The ultimate example was provided by that other stoic, Pete Sampras. In 2002, at just 31 years old, the most prolific of all male Grand Slam singles champions (13 titles, at the time) was clearly slipping.
Sampras had dropped to No. 17 by the US Open. But driven by the undeclared inner conviction that he still had a big win in him, he mastered his own doubts and those of others and unexpectedly won the tournament—and never swung a racquet in anger again.
The man from whom Sampras took his pound of flesh in that final was Andre Agassi, who would soon stage a spectacular farewell of his own. He was ranked No. 39 when he played his final match at the 2006 US Open. Anyone who witnessed his fourth-round loss to Benjamin Becker—or the ensuing, pitch-perfect retirement speech he then made, on-court—will never forget that emotional, inspirational moment.
