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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.

Alex Dalenberg

Read when you’ve got time to spare.

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]

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.

Tom Brady Is Retiring a Year Too Late, but Now Has No Lingering Questions [2023]

Brady’s year of unretirement was a spectacular failure on the field and off, but now the NFL’s GOAT can officially walk away from his football career knowing the time was right.

For Tom Brady, the Cost of Greatness Finally Became Too Great [2023]

Throughout his legendary career, Tom Brady gave all of himself to football. There was a price.

A Secret Plan, a Bombshell Lawsuit, and a Soccer Match: Inside Tom Brady’s Un-Retirement [2022]

If Brady had his way, he would have been running — and potentially quarterbacking — a Patriots division rival. Instead, a series of unforeseen events led him back to Tampa.

Is Tom Brady The GOATiest Of All The GOATs? [2022]

With legendary quarterback Tom Brady officially retiring (yes, we really mean it now), the accolades are pouring in.

Tom Brady Is Just F***ing Impossible [2021]

“In the end, there is always Brady, smiling that idiot smile of his while a soft monsoon of confetti envelops him. He’s been doing this for so long that I can barely grasp it.”

The Story Behind the Split of Tom Brady, Bill Belichick and the Patriots [2020]

It’s finally official: Tom Brady will not be forever a Patriot. But in reality, the quarterback's split with New England can be traced back much further than this offseason.

Why We Love to Hate Tom Brady [2018]

The Gwyneth Paltrow of the NFL must be stopped.

Tom Brady’s Most Dangerous Game [2017]

The Patriots legend thinks he can play until he’s 45 without sacrificing body, mind or integrity. But his future is not just in his hands.

Tom Brady Has Never Eaten a Strawberry in His Entire Life [2016]

And he doesn’t plan on trying one now.

Tom Brady Cannot Stop [2015]

A season in the charmed, cutthroat life of the N.F.L.’s most enigmatic quarterback.

Fortunately for Patriots, Tom Brady Chose Football [2015]

John Hughes has been laughing about the possibility for a decade. He was the man tasked with ruining it all: Tom Brady’s football career, the Patriots’ future dynasty and, really, the entire American sports landscape.

Brady, Manning and the Rivalry [2011]

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]

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.

The Ultimate Teammate [2005]

The Super Bowl rings are nice, but his greatest achievement grows out of a generosity of spirit that makes him a leader in the toughest times.