In the endless web of NFL “what ifs,” few stories are as jaw-dropping as the true origin of how the New England Patriots landed Tom Brady — and believe it or not, we have the New York Jets to thank for it.
Pablo Torre, on his podcast Pablo Torre Finds Out, recently uncovered a chain of events that sounds like something straight out of a sports-themed multiverse. We’ve always known that Brady was famously picked 199th overall in the 2000 NFL Draft — the ultimate underdog story. But what we didn’t know was how that pick came to be in the Patriots’ hands in the first place.
It turns out, that #199 pick wasn’t just a regular selection — it was a compensatory pick awarded by the NFL. These picks are given to teams that lose valuable players in free agency, but the actual formula for awarding them has always been secretive.
So, who did the Patriots lose to earn that golden compensatory pick?
A guy named Tom Tupa — a name most casual fans probably wouldn’t even recognize. But his story? It’s legendary.
Tupa was a rare breed: a punter and a quarterback. Back in his Cleveland Browns days, head coach Bill Belichick signed him not as a QB, but as a holder for field goals. In that role, Tupa made history as the first player to ever score a 2-point conversion — faking a field goal attempt and taking it in himself. That moment earned him the nickname “2-point Tupa.”
When Belichick moved to New England, Tupa followed. But in 1999, Tupa signed with the Jets — where Belichick, ironically, was then an assistant under Bill Parcells. The Jets made him the highest-paid punter in the NFL, and Tupa delivered with an All-Pro season.
Then came the twist.
In one game, injuries forced the Jets to play Tupa at quarterback — and he lit it up for three quarters. But then Parcells bizarrely benched him in the 4th, put in a backup QB who threw two interceptions, and the Jets lost by two. That loss ended up costing the Jets a playoff spot, finishing 8-8 and missing out by just one game.
That one failure was enough for Parcells to step down. Belichick was then briefly named Jets head coach — for all of one day — before quitting and jumping ship to New England instead.
Here’s the kicker: because the Jets gave Tupa a big payday in 1999, and because the Patriots lost him that same year, New England was granted a compensatory 6th-round pick in 2000.