I’m a Super Bowl-winning QB and No.1 pick who was once NFL’s best-paid player, now I own three wineries
Drew Bledsoe will forever be known as the man who passed the baton to Tom Brady. But the former New England Patriots quarterback was a star in his own right, and without the foundations he laid, Bill Belichick may not have been able to establish the iconic dynasty. GettyBledsoe helped prepare the ground for Brady’s dynasty[/caption] Bledsoe was picked first overall in the 1993 NFL Draft and started for the Patriots until 2001 when, fresh off signing a 10-year deal worth $103 million that made him the league’s highest-paid player, he was injured in Week 2. Brady took over and won the first of seven rings — it would not have been possible if the man he replaced hadn’t taken over from him in the AFC Championship game after the GOAT himself was hobbled. Bledsoe was traded to the AFC East rival Buffalo Bills and retired as a Dallas Cowboy in 2007 with $80 million in career earnings after seeing Tony Romo take over as starter. At the time, he was fifth in NFL history for pass attempts (6,717) and completions (3,839), seventh in passing yards (44,611), and thirteenth in touchdown passes (251). Success has continued off the field as Bledsoe went into winemaking — a decision that he felt forced to defend. “It’s interesting, when we broke into the business, one of the things that we had to overcome was this stigma about athletes getting into wine,” he told Forbes in 2024. “I knew from the very beginning, that we wanted to have a real wine project, not an endorsement deal, not some c***** wine we’re going to sell to football fans. “We wanted to actually have something that was rooted in the earth’s and so when we started, it was really important to me that we started with a bare piece of dirt.” In 2007, Bledsoe founded his first winery, Doubleback, in his hometown of Walla Walla, Washington — a state which is becoming a real hotspot for vineyards. It was a family affair with his wife, Maura, and four children all getting dirt on their hands. Patriots owner Robert Kraft visited Bledsoe for a sampleNew England Patriots YouTube GettyThe former No.1 pick ended up playing for the Bills[/caption] “We started in the real way; we started with dirt. Got out with our kids, put vines in the ground with our own hands, in my hometown of Walla Walla,” he told Paste Magazine. “I grew up there, got to go live out my childhood dream in the NFL and then doubled back and came back home. That’s where the Doubleback name comes from.” Doubleback specializes in Cabernet Sauvignon. The retired quarterback’s second offering, The Bledsoe Family Winery, targets wines at an ‘accessible’ price point. His third, Bledsoe McDaniels, with business partner Josh McDaniels (no relation to the former Pats coach) focuses on Pinot Noir. Pro Bowl wide receiver Sidney Rice has also got into the wine game and joined Bledsoe for a roundtable on the industry. NFL's Greatest...... Ranking the top 10...... Quarterbacks of all-time – Can anyone better Tom Brady? Wide receivers of all-time – Does Randy Moss or Jerry Rice come out on top? Running backs of all-time – Stacking Jim Brown, Barrie Sanders, Walter Payton, Emmett Smith and more Tight ends of all-time – How does Travis Kelce compare? “As it pertains to the roundtable and what’s going on in the wine world right now, it’s really exciting to me, because there are more guys like Sidney coming into the business that are serious about the wine,” Bledsoe explained to Forbes. “They’re serious about what’s inside all of that and just not just putting their name on something and putting that out to the world. “It’s great for me just personally and selfishly because now I think the stigma is being flipped a little bit, where people aren’t going to look down their nose and they’re going to see these athletes are serious about making good juice. “More athletes are getting back into wine now than they were back in the day. A lot more that are serious about it too. Both of those things are great.” Bledsoe’s company had 75 employees as of 2024 and he has managed to build a successful life for himself off the field. If the 53-year-old ever wonders what may have been if Brady hadn’t taken his job all those years ago, he hasn’t let on. He did, however, get revenge in Netflix’s now-infamous special ‘The Roast of Tom Brady.’ “So I’ve got to admit, I’m a little bit nervous tonight. I truly am,” he began. “Because the last time I was up on stage before Tom Brady, I ended up in the hospital for five days and I lost my damn job.” Bledsoe then managed to get a couple of adverts in for his new venture. “You know, when most people lose their jobs, they start drinking. I started a winery. It’s called Doubleback. It’s named after what Tom does every time he walks past a mirror,” he joked. “My favorite wine
Drew Bledsoe will forever be known as the man who passed the baton to Tom Brady.
But the former New England Patriots quarterback was a star in his own right, and without the foundations he laid, Bill Belichick may not have been able to establish the iconic dynasty.
Bledsoe was picked first overall in the 1993 NFL Draft and started for the Patriots until 2001 when, fresh off signing a 10-year deal worth $103 million that made him the league’s highest-paid player, he was injured in Week 2.
Brady took over and won the first of seven rings — it would not have been possible if the man he replaced hadn’t taken over from him in the AFC Championship game after the GOAT himself was hobbled.
Bledsoe was traded to the AFC East rival Buffalo Bills and retired as a Dallas Cowboy in 2007 with $80 million in career earnings after seeing Tony Romo take over as starter.
At the time, he was fifth in NFL history for pass attempts (6,717) and completions (3,839), seventh in passing yards (44,611), and thirteenth in touchdown passes (251).
Success has continued off the field as Bledsoe went into winemaking — a decision that he felt forced to defend.
“It’s interesting, when we broke into the business, one of the things that we had to overcome was this stigma about athletes getting into wine,” he told Forbes in 2024.
“I knew from the very beginning, that we wanted to have a real wine project, not an endorsement deal, not some c***** wine we’re going to sell to football fans.
“We wanted to actually have something that was rooted in the earth’s and so when we started, it was really important to me that we started with a bare piece of dirt.”
In 2007, Bledsoe founded his first winery, Doubleback, in his hometown of Walla Walla, Washington — a state which is becoming a real hotspot for vineyards.
It was a family affair with his wife, Maura, and four children all getting dirt on their hands.
“We started in the real way; we started with dirt. Got out with our kids, put vines in the ground with our own hands, in my hometown of Walla Walla,” he told Paste Magazine.
“I grew up there, got to go live out my childhood dream in the NFL and then doubled back and came back home. That’s where the Doubleback name comes from.”
Doubleback specializes in Cabernet Sauvignon.
The retired quarterback’s second offering, The Bledsoe Family Winery, targets wines at an ‘accessible’ price point.
His third, Bledsoe McDaniels, with business partner Josh McDaniels (no relation to the former Pats coach) focuses on Pinot Noir.
Pro Bowl wide receiver Sidney Rice has also got into the wine game and joined Bledsoe for a roundtable on the industry.
NFL's Greatest......
Ranking the top 10......
Quarterbacks of all-time – Can anyone better Tom Brady?
Wide receivers of all-time – Does Randy Moss or Jerry Rice come out on top?
Running backs of all-time – Stacking Jim Brown, Barrie Sanders, Walter Payton, Emmett Smith and more
Tight ends of all-time – How does Travis Kelce compare?
“As it pertains to the roundtable and what’s going on in the wine world right now, it’s really exciting to me, because there are more guys like Sidney coming into the business that are serious about the wine,” Bledsoe explained to Forbes.
“They’re serious about what’s inside all of that and just not just putting their name on something and putting that out to the world.
“It’s great for me just personally and selfishly because now I think the stigma is being flipped a little bit, where people aren’t going to look down their nose and they’re going to see these athletes are serious about making good juice.
“More athletes are getting back into wine now than they were back in the day. A lot more that are serious about it too. Both of those things are great.”
Bledsoe’s company had 75 employees as of 2024 and he has managed to build a successful life for himself off the field.
If the 53-year-old ever wonders what may have been if Brady hadn’t taken his job all those years ago, he hasn’t let on.
He did, however, get revenge in Netflix’s now-infamous special ‘The Roast of Tom Brady.’
“So I’ve got to admit, I’m a little bit nervous tonight. I truly am,” he began. “Because the last time I was up on stage before Tom Brady, I ended up in the hospital for five days and I lost my damn job.”
Bledsoe then managed to get a couple of adverts in for his new venture.
“You know, when most people lose their jobs, they start drinking. I started a winery. It’s called Doubleback. It’s named after what Tom does every time he walks past a mirror,” he joked.
“My favorite wine is our world-class cabernet. Tom’s favorite wine is, ‘Where’s the flag?’”
The most controversial joke came with a jibe poking fun at the breakdown of Brady’s marriage with Gisele Bundchen in 2022.
“Look, buddy, you have more rings than I do, but I’ve experienced a couple of things you’ll never experience,” he continued. “The feeling of being the number one overall draft pick in the NFL, and a 28th wedding anniversary, it was yesterday.”
Bledsoe may not have a $375 million contract with Fox Sports, he didn’t start the Super Bowl which earned him his only ring, but he has plenty of things to raise a toast to — and plenty of wine to put in the glass.
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