NOTE: This story originally ran on on Jan. 25. For more on Drew Bledsoe’s life after football, watch the full feature, reported by Jeremy Schaap and produced by Max Brodsky, Sunday night on E:60 at 9 ET on ESPN.
DREW BLEDSOE PULLS a sip of red wine into his mouth. He makes a swooshing sound, like he’s trying to imitate a vacuum cleaner. “The one on the right, the ‘B,’ has a little harder edges,” he says. “‘D’ still has structure, but it also has more balance.”
He’s sitting at the head of a long wooden table in the tasting room at Doubleback, the winery he owns in Walla Walla, Washington. Samples of three pinot noirs from Oregon’s Willamette Valley have been poured into glasses in front of him. The wine in two of them has been made from grapes grown in specific vineyards. The third wine is a blend of the two.
One of these samples will be bottled by Bledsoe/McDaniels, the former NFL quarterback’s third wine project. Josh McDaniels, no relation to the Patriots offensive coordinator of the same name, is a trained enologist who does the actual winemaking for all of Bledsoe’s labels. But Bledsoe’s opinions carry at least equal weight.
Bledsoe tastes the wines again. “‘D’ is the most purely pleasurable right now,” he announces. “‘B’ is pretty structured. And it just seems to me that, for what we’re trying to accomplish with this blend, we want a little more of that friendly ‘wow’ factor. We want people to drink it and smile.”
Bledsoe finished his NFL career in 2007 after 14 years, 44,611 passing yards, 251 touchdowns and two Super Bowls. But his tenures as the starting quarterback for the Patriots, Bills and Cowboys all ended abruptly, and with bitterness. At 35, he was being offered backup positions on NFL rosters. Compared with that, starting a second career in wine seemed too enticing to put off.
Bledsoe was seduced by wine’s magic about five years into his career, as a 25-year-old living outside Boston. From there, he set out to learn everything he could about it — or, at least, more than his teammates knew. “It would be this whole kind of discussion about the texture, and how it tastes in your mouth, and what was the best food to eat with it,” says Ted Johnson, who played with Bledsoe in New England. “We’d go out to dinners, and you knew he was going to order the wine and it was going to be this whole process.”
Plenty of big names in sports were already dabbling in wine, from Tom Seaver to Ernie Els to Mario Andretti. Nearly all of them considered it a hobby. Bledsoe was looking for more. “This isn’t just ‘dumb jock throws money at a winery,'” he says. He smiles. “Or even ‘smart jock.'” If it was merely a hobby, he wouldn’t have bothered to get involved. “I wanted to learn,” he says. “And if you come into it with that attitude, with true humility, it’s amazing what people will tell you.”
Since he’d left Walla Walla for fame and NFL fortune, the unprepossessing farming and manufacturing town on the Oregon border had developed into one of the better places in America to grow wine grapes. It made sense for Bledsoe to start his business there, rather than in California’s Napa Valley, which tends to attract most of wine’s wealthy amateurs. Not everybody was thrilled to see him. “My first thought was, ‘Yeah, just what we need,'” says Greg Harrington, a New York transplant whose Gramercy Cellars is one of Walla Walla’s most respected wineries. “‘Some former pro athlete who knows nothing about wine.'”
Thirteen years on, Bledsoe’s Doubleback cabernet sauvignons have earned a reputation as some of the region’s best. They’re also among the most coveted. He launched a second project, Bledsoe Family Winery, so he could use other grape varieties, such as syrah and chardonnay, and also sell some wine for less than the $90 to $120 a bottle that Doubleback commands. The Bledsoe/McDaniels label is designed for small lots of geeky wines, such as three Walla Walla syrahs that are each made from fruit grown in different types of soil. “He’s truly into learning and tasting,” an admiring Harrington says now about Bledsoe. “Not just the wines you’re ‘supposed to’ appreciate but esoteric stuff. Sommelier stuff.”
Merely starting a wine business helped ease Bledsoe out of the locker room. He admits it would have been difficult otherwise; the sport he’d built his life around since childhood had left a football-sized hole. But Bledsoe is also preternaturally competitive. Only when the critical and commercial success of his wines was assured was he able to put his playing career, the business finished and unfinished, safely in the past.
AS LATE AS 1990, the year that Bledsoe graduated from Walla Walla High School, tumbleweeds still blew down Main Street on windy afternoons. The town of some 27,000 was known for its euphonious name, the state penitentiary and the quality of its sweet onions. High school sports brought a measure of pride. “It’s the kind of place where the stores close on Friday nights and everybody goes to the football game,” says Adam Bledsoe, Drew’s younger brother.
But like many of the former processing and manufacturing centers of eastern Washington, it was slowly dying. “We lost two canneries, two lumber mills, a can manufacturing plant,” says Chris Figgins, who grew up on the same street as Bledsoe and made his Doubleback wines until 2014. The wine industry hadn’t yet emerged to take their place. At least 120 commercial wineries are operating in Walla Walla today, but only five were producing wine as of 1990. Few of the wines they made ever left the state.
One of those was owned and run by Gary Figgins, Chris’ father. He’d started making his Leonetti wines with an Army Reserve buddy as a glorified home ec project. He did it in Walla Walla only because he happened to live there; the grapes came from many miles west. By the time Bledsoe, who’d played three seasons at Washington State, became the first player chosen in the 1993 NFL draft, Leonetti merlot and cabernet had started to develop a cult following. The mailing list had a waiting list.
The Leonetti name meant little to Bledsoe. And once he started to care about what he was drinking, he gravitated toward the juicy, unsubtle Napa cabernets that earned the highest scores from the critics and, not so incidentally, cost the most. Those were wines that seemed appropriate for an All-Pro quarterback. As his interest deepened, he’d invite teammates to his house — Mike Vrabel, Bruce Armstrong, Damon Huard, others — and ask each to bring a bottle. They’d taste all the wines without knowing which was which. Eventually, Bledsoe noticed that when a Washington wine was included, the bottle nearly always ranked the highest. And emptied first.
Soon he was scouring wine shops in greater Boston in search of Leonetti and some of the other emerging Walla Walla labels. One day, he called Chris Figgins, who’d started working with his father. Chris was two years younger than Bledsoe. They’d hung out together a bit in high school, at opposite ends of the same social group, but hadn’t crossed paths in years. With a laugh at his own brazenness, Bledsoe remembers the conversation like this: “Hey, Chris, it’s Drew. We haven’t talked in a long time. Listen, do you think you can move me up on the list so I can buy some of your wine?”
After he retired, Bledsoe flew to Walla Walla to figure out how to start a winery. He’d been among the best at what he did since he was 13, reaching the highest echelons of his sport. With wine, for the first time, he was an unheralded rookie. He relished the challenge. “I was successful as a football player,” he says. “Can I start over at something totally different and become successful at that too?”
By then, Chris Figgins was making the wine at Leonetti. “He’d become this winemaking rock star while I was off playing football,” Bledsoe says. Bledsoe called, explained what he was hoping to do and asked whether Figgins would be open to a partnership. One afternoon, they jumped into Figgins’ truck and went for a drive. Ostensibly, they were scouting vineyard sites. But Figgins also wanted to make sure that Bledsoe was the same benevolent neighbor he used to know. “Fame and fortune changes people,” he says. “I wanted to see what kind of guy he was.”
Figgins didn’t want to work with anyone, famous neighbor or not, whose ambition was merely to see his name on a label. “I call it ‘just add wine,'” he says. “If all he wanted me to do is make some wine that he can slap ‘Bledsoe’ on, I wasn’t interested.” Bledsoe remembers sitting at a traffic light, not far from what would later become the site of Doubleback. Figgins turned to him and asked a question. “He tried to just slide it in,” Bledsoe says, “but I knew that my answer would be really important. He goes, ‘So, what kind of wines are you into?'”
Rather than naming one of the upscale brands of Napa cabernet, the answer that Figgins expected, Bledsoe explained that his favorite wines came from the Barolo area in northern Italy. “He kind of looked over at me, like ‘maybe this could work.'”
That test was the first of many indications to Bledsoe that his status as a football star wasn’t always going to be relevant in his new surroundings. Soon after, Figgins brought him to a national wine conference in Reno, Nevada. After the program ended, they visited a local wine bar.
Bledsoe stepped forward and made the introductions to the owner. “I’m Drew Bledsoe,” he said. “And this is Chris Figgins.” Instantly, the owner knew he had a celebrity in the house.
“Chris Figgins?” he said. “Really? Would you sign some bottles for me?”
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ONE SNOWY NIGHT in January, Bledsoe sits sprawled across a restaurant banquette in downtown Walla Walla. “Haven’t seen you in a while,” the manager says with a laugh as he passes the table. It turns out that Bledsoe was there the previous night.
Bledsoe has a bottle of one of his own syrahs in front of him and a 2005 Barolo that someone has given him. He pours some of the Barolo and moves his nose close. A whiff makes him rhapsodize: “I love this. It’s just so different than anything else.” He takes a sip. “It’s not obvious,” he says. “It’s intricate. It’s layered. It’s complex.”
McDaniels arrives and sits down across the table. Bledsoe slides him two glasses. As he pours, he reminds McDaniels that the best wine he’d ever had was a Barolo. It was made by the producer Giacomo Conterno from grapes harvested in 1961, which means it was about half a century old by the time Bledsoe tasted it. “It was this ethereal, magical sensory overload experience,” he says. McDaniels nods vigorously, his eyes wide.
After the 2014 vintage, Figgins handed off Doubleback to McDaniels, his protégé. These days, Bledsoe and McDaniels talk daily. And though Bledsoe has raised his three sons and a daughter in Bend, Oregon, where his wife, Maura, has family ties, he travels to Walla Walla nearly every week, sometimes multiple times. That much travel is unsustainable, he knows. When the youngest of his children leaves for college in a year and a half, he and Maura will move their primary residence to Washington.
On the big screen above them, and lots of little screens around the room, Clemson and LSU are playing for the national championship. Since his retirement, Bledsoe has stayed close to the game. In Bend, he served as the offensive coordinator for all three of his boys’ high school teams. (One of his sons, John, is now a quarterback at Washington State.) That’s over now, but Bledsoe still likes to throw the football when he can. “It just takes a little while to get warmed up,” he says.
He also follows football as a fan. “He’s the real thing — he’s going to be terrific” he says, watching Trevor Lawrence complete a pass. “I like watching good quarterbacks. I do wish they’d pull back the camera angle more often so you can see the whole field.” He wants to see where the receivers are and whether the quarterback makes the right decision. “Timing,” he says. “Accuracy. Going to the right place at the right time. That’s what makes a quarterback. Not the strength of your arm. There weren’t many balls that I threw as hard as I could.”
Dabo Swinney appears on the screen, nodding hard and clapping his hands. Watching him, Bledsoe can’t help but compare him with Alabama coach Nick Saban. “If you have the chance to go anywhere and play for any of the top programs,” he says, “you want to play for Dabo or you want to play for Saban? Dabo actually looks like he’s having fun out there.” Saban, meanwhile, brings to mind his former coach in New England, Bill Belichick. “Just a machine,” Bledsoe says.
During the Patriots’ 2001 championship season, Belichick made the controversial decision to keep Tom Brady as the team’s quarterback once Bledsoe, who had been the starter, recovered from a gruesome chest injury. At the time, Brady seemed like an unpolished striver who already had exceeded expectations. Belichick had a career losing record in the NFL. Eight more Super Bowl appearances later, they’re both considered the best ever at what they do.
Bledsoe has watched their ascent from a unique perspective. He finds it difficult to assess Belichick’s achievements because they’ve all happened with Brady as his quarterback and Robert Kraft as his owner. “It would be really hard for him to do what he does without those two bracketing him,” he says. “He’s got Kraft, who supplies the heart and soul. He really loves his players. And then he’s got Tommy, who still has an underdog’s chip on his shoulder 20 years in.”
That attitude, more than the way Brady plays on Sunday afternoons, is what Bledsoe believes sets the Pats star apart from every other quarterback. “It’s the example he sets for everyone else in the building,” he says. That’s far from unconventional wisdom, but coming from the man who lost his job to Brady, it’s easy to wonder whether there are layers of emotions coloring his perceptions.
Bledsoe denies it. “Tommy’s a great friend, and I have more respect for him than anybody,” he says. “He’s always kind of been a mid- to low-tier talent, but he’s at the pinnacle of leadership, and example, and work ethic. I mean, here’s Tom Brady, married to Gisele, these kids have grown up watching him. And you show up as part of the Patriots organization, and that dude’s working harder than you? You’re like, ‘I’d better get here earlier tomorrow. I’d better make sure my stuff is all done.'”
Asked to compare making wine with playing football, Bledsoe pauses and considers. “There’s nothing that could ever match the thrill of playing quarterback in the NFL,” he says. “Seventy thousand people screaming. Or even more fun, 70,000 opposing fans going quiet.” He seems wistful for a moment, as if the highlight reel of his pro career is spooling somewhere inside his head.
Then the young Drew Bledsoe fades back into the past and a middle-aged businessman takes his place. “But there is an equal feeling of accomplishment in wine,” he says firmly. “And it feels a lot better on a Monday morning.”
RUNNING A WINERY is farming and chemistry, marketing and customer service. Bledsoe knew he’d love the wine part of the wine business. What he couldn’t predict was how easily he’d take to the business part.
How could he? His father was a football coach; his mother was a teacher. It wasn’t as if he had entrepreneurship in his blood. But he taught himself how to run his company just like he learned how to appreciate wine, not by reading books about it but by doing it. “As a person now, I see him as a business guy,” Maura says. “He’s got a brilliant, brilliant business mind.”
“I think the thing that I enjoy the most about the business is that it’s so multifaceted,” he says. “You’re a farmer first … and then you’re into production, winemaking, and there’s so much to learn there. And then marketing and distribution and fulfillment and customer service. And I’ve had to learn way more about accounting than I ever thought I would ever learn in my life.”
He shows off the unconventional design of his Bledsoe/McDaniels bottles, which are designed to make a consumer look at the label on the back to get information about the wine. “If you pick up a bottle,” he says, “you buy that bottle 87% of the time.”
“Drew is a very smart guy,” Figgins says. “He dove into the business side of things with a lot of time and effort.” Bledsoe remains the most famous athlete in the history of his hometown and probably will be for a while. But slowly, he’s becoming known as more than just an ex-quarterback.
He was sitting outside a restaurant the other day when a couple walked past. The man stopped and stared hard. “I think that’s Bledsoe,” he said.
The woman with him grew excited. “You mean the wine guy?”
Telling the story, Bledsoe breaks out in a grin. “And that,” he says, “is super friggin’ flattering.”