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Why Tom Brady Was the Best (And Also the Worst)

Revisiting 23 years of great sports writing about the legendary quarterback—by those who loved and loathed watching him play.

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Tom Brady is retiring and this time it seems like he really means it. The 45-year-old quarterback announced this week that his football playing days are over “for good”, ending one of the most storied careers in sports history. To many football fans, he’s the greatest of all time. For others, he’s absolutely infuriating. And for some tortured souls—it’s both. Either way, the legend of Tom Brady has produced a lot of great sports writing over the decades. We’ve rounded up some of the best articles written about Brady during his 23 years in the NFL, from early coverage of the New England Patriots dynasty to his age-defying campaign with the Tampa Bay Buccaneers.

Image by Justin K. Aller / Stringer

Tom Brady Retires: The Revised Edition [2023]

Ben Shpigel
The New York Times

One year ago, on Feb. 1, 2022, Tom Brady announced his retirement. On Wednesday, he announced his retirement again. To keep things simple, we took last year’s article and made a few small edits. Here is the article from a year ago, with some deletions and insertions.

Brady, Manning and the Rivalry [2011]

Bill Simmons

Webster’s defines a rivalry as “competition for the same objective or for superiority in the same field.” That means Tom Brady and Peyton Manning have a rivalry. A phenomenal one, actually. And yet, it doesn’t feel like one.

The Comeback: Tom Brady [2009]

Adam Rapoport

Admit it—for a while there, you thought Tom Brady was done. He blew out his knee, got all soft and mushy and married Gisele, couldn't hit Randy Moss to save his ass. But as the Tennessee Titans secondary can testify, Captain America doesn't go down that easy.