At a tasting event for Doubleback, the Walla Walla, Washington, winery that former quarterback Drew Bledsoe started after retiring from the NFL in 2007, the founder is easy to spot. At 6-foot-5, he is the tallest one in the room, and unlike just about everyone else in attendance, he isn’t dressed in blue-and-Ecto-Cooler-green garb. He laughs when he gets ribbed for holding a Seattle-area preview for his latest vintages on the same day as a Seahawks playoff game. "We scheduled it for a Saturday just so this wouldn’t happen!" he says in mock protest to a woman in a Russell Wilson jersey who, earlier, had been raving to a friend about how much she was enjoying the rosé, her go-to "porch wine." Luckily, the event’s location, Passing Time, a winery in Woodinville, Washington, that fellow retired quarterbacks Dan Marino and Damon Huard own, has a television over the bar.

"There are a million wonderful, amazing things about playing professional football," Bledsoe says while sitting at a big, beautiful wooden table in the center of the room that was crafted by another former quarterback from Washington, Jake Locker. Bledsoe pauses to shake his head in mild frustration at the Seahawks, who are not looking too good. (Seattle’s Pete Carroll was Bledsoe’s coach in New England in the late ’90s, and Bledsoe still roots for his success.) "It’s every kid’s childhood dream — at least, it’s what I grew up with. But one of the downsides is just, you know, it generally doesn’t end in storybook fashion."

The Seahawks will lose the game to the Falcons, 36–20, and later that night the New England Patriots will send the Houston Texans packing, 34–16. Both the Falcons and the Patriots will go on to win their conference title games. And on February 5, Atlanta and New England will face off in Super Bowl LI. For the Patriots, it will be the seventh Super Bowl appearance since the 2001 season, one of the most remarkable eras of dominance in all of sports. It will be vindication for Tom Brady, who was forced to sit out four games at the start of the season due to the league’s Deflategate investigation. Brady has won three Super Bowl MVPs in his career and hoisted the Lombardi Trophy four times. He is the leader of a for-the-ages dynasty and arguably the GOAT at his position. And he got his big break thanks to one of the worst days of Bledsoe’s life.

Early in training camp before the 2001 season, Bledsoe stood in the Pats huddle, looked around at his offensive line, and was struck by how optimistic he felt. "We have a chance," he told his guys, who were playing for a team that had won just five games the season prior. He was right, but not in the way that he had hoped. In the fourth quarter of the second game of the season, against the New York Jets, Bledsoe scrambled out of the pocket, ran the ball toward the first-down marker on the right sideline, and was leveled by Mo Lewis just as he was heading out of bounds.

Brady, then Bledsoe’s backup, would later describe the collision as "the loudest hit I could ever remember hearing," and Bledsoe’s face mask as "smashed." Before the season, Bledsoe had signed a 10-year, $103 million contract designed to make him the highest-paid player in NFL history and a Patriot for life. By the end of the season, though, it was Brady standing on the Super Bowl podium, accepting the MVP prize. For Bledsoe, knowing that his preseason prediction had been right was little solace. Those childhood dreams had included winning a Super Bowl, but not being stuck on the sideline when it happened. And while his NFL career would continue for another five seasons, he would not suit up for the New England Patriots again.

So many former professional athletes, absent the pursuits that for so long dominated their worlds, spend the rest of their lifetimes chasing memories, relitigating pasts, and dearly missing their primes. But if anyone has been able to gracefully shelve one truncated storybook and start scribbling page after page in a new one, it’s Bledsoe. He is simply too busy to be bitter, too distracted to be disillusioned, too immersed in his favorite places — from Walla Walla; to Bend, Oregon; to Whitefish, Montana — to have much time to think back on what might have been in New England.

It’s been 15 years since that first Patriots Super Bowl win, and 10 years since Bledsoe retired from football. Since then, he has helped buddies launch businesses — a custom-ski company here, a coffee enterprise there — and started one of his own: the highly respected Doubleback, whose name references his own boomerang exit and return back to the Pacific Northwest. He has coached his three sons’ high school football team in Bend, where his family now lives, and has organized ski trips in areas of British Columbia that are only accessible via private helicopter. (Sometimes he even marries his interests, bringing mini-kegs of his wine onto the slopes.) After living his dreams, he’s living the dream.

Since retiring, he says, "I haven’t had any days where I’ve gotten out of bed and wondered what I was going to do." He has successfully built a life outside of football in part because, even while he was in football, the game never consumed him entirely.

It was during Drew’s sophomore year at Walla Walla High School that his father, Mac, realized he couldn’t fully trust his teenage son. The revelation didn’t stem from any sort of adolescent drama; Drew had a good head on his shoulders and an arm that had tossed impressive spirals ever since he was a little kid hanging around the football clinics his dad ran in the summer. Drew’s work ethic and clear talent on the football field helped shield Mac, an English teacher and the offensive coordinator at Drew’s school, from most charges of nepotism, even though the coach’s boy was starting at quarterback. Drew was a good student and an even better skier — Mac Bledsoe’s dream boy.

But early that football season, Drew took an ugly hit. He finished the game, then later wound up in the hospital with a badly bruised liver. "Maybe one of the hardest things about coaching him," says Mac, who is now 71 and lives in Montana with Drew’s mother, Barbara, "was that it made me very vigilant that he wasn’t going to tell me he was hurt. He was going to go back in. After he had that bruised liver, it just made me say, ‘I’ve got to watch him.’"

Mac never wound up having to intervene while Drew was at Walla Walla, but he kept a closer eye on his son nonetheless. He watched Drew throw for a state-record 509 yards in a game during his senior year of high school. He watched Drew go off to Washington State and earn the starting quarterback job partway through his true freshman season, set a number of school records in his three years, and win a Copper Bowl. (His 476 yards in that bowl game may not have lived up to his record high school night, but it was still the best single-game total in school history to that point.) And he watched Drew declare for the 1993 NFL draft after his junior year, go first overall to the struggling New England Patriots, become (at 22) the youngest quarterback in NFL history to make a Pro Bowl, pose with his contemporary Brett Favre in a milk ad promoting Super Bowl XXXI, and eventually sign that 10-year Patriots contract in March 2001.

Then, in September 2001, he watched his son’s career change completely. After being leveled by Lewis, Bledsoe took the field for the next series, but he had trouble remembering the two-minute-drill plays. He walked off the field toward the trainers, figuring he’d "gotten his bell rung," which is how he almost always puts it in the retelling. He had gotten his bell rung, yes, but the impact had also sheared off part of a blood vessel near his ribs, causing internal bleeding. After the team medical staff insisted he go to the hospital, doctors removed between three and four liters of blood from his chest.

When Mac arrived at Drew’s hospital room, he says, his son’s first comments didn’t have to do with his freak injury or future prognosis — not directly, at least. "The world’s going to get to see what a good quarterback Tom Brady is," Mac remembers Drew saying about his backup, who had been drafted out of Michigan in the sixth round in 2000. "He’s gonna be able to sign a free-agent contract with any team he wants."

Mac chuckles at how that sounds now. "Drew just didn’t ever think," he says, "it would be with the Pats."

In winemaking, the word terroir refers to the unique set of natural variables — the interplay of things like soil, climate, and topography — that manifest in the grape and, eventually, on the palate. One of Doubleback’s estate vineyards in Walla Walla, called McQueen in honor of Drew’s great-grandfather’s middle name, which Drew shares, sits on top of a breezy ridge. The wind beats on the grapes as they grow, and all the banging around thickens their skin. The resulting product is rich in color and complexity and character.

Bledsoe, too, is the product of his environment, the kind of person with a strong terroir. He descends from cowboys, and he grew up roaming the ranches and the mountain ranges of the American Northwest. (When his entire family piled into a plane in 1993 to fly to New York for the NFL draft, he described it as "like the Waltons go to New York.") His grandfather, Stu Bledsoe, had a World War II Naval squadron mate who had grown up on a cattle ranch "and made it sound really romantic," Drew says. "So when he got out of the military, he decided to be a rancher." Stu moved his family from California to Washington in pursuit of the lifestyle. "Turns out it wasn’t super romantic," says Drew, "it was just a lot of brutally hard work." But Stu studied animal husbandry at Washington State, and all that hard labor created a lasting set of family values: an appreciation for the land, a respect for industriousness, and a willingness to strike out on one’s own (even if doing so sometimes means striking out).

When Drew was about 2 years old, as soon as his toddler feet were big enough to be reasonably strapped into a pair of skis, Mac started taking him skiing around Washington’s Cascade mountain region, the same way Stu had done with Mac. When Barbara Bledsoe became pregnant with Adam, Drew’s younger brother, and cut back her time on the slopes, "Drew became my ski partner," Mac says. Drew was 6 at the time. Mac had friends who worked on ski patrol at the nearby mountains Alpental and Stevens Pass, and they had a deal: If Mac showed up at the mountain super-early — say 6 a.m. — and helped them shovel out lift towers while they detonated avalanche control explosives, he could tool around on the mountain before it opened to the public for the day.

"And I’d show up with this little guy in these red coveralls," Mac says, "and they’d say, ‘Uh, what are you gonna do about him?’ And I’d say, ‘Worry about yourselves; he’s great.’ We’d go down these incredibly steep mountains, such deep snow, and he went everywhere."

Years later, after Drew’s second season in the NFL, he surprised his father with a Christmas present: a heli-skiing trip to British Columbia. It was the first time either of them had gotten to the top of a run via helicopter. "It’s like, he’s a schoolteacher and a football coach," Drew says. "[Heli]-skiing was never going to be in the budget. Dad’s a big cowboy — big ol’ mustache, the whole deal — and I just remember sitting across from him, lifting off for the first time, and a big tear was just running down his face."

Mac says the trip is "up there in the top 10 of my life’s experiences." They were lucky with weather and were able to ski areas that their guide said hadn’t enjoyed such ideal conditions in nearly a decade. "And doing that with my son — that multiplied the experience times 10," Mac says. "Because in my mind, every day, when we would be loading up in the helicopter, or getting off on top of a mountain — I’d be replaying, in my mind, those pictures of him in his little red snow suit, up there on with the ski patrol."

The only problem came when Drew referenced the trip during a conversation with New England owner Robert Kraft. "The second contract I signed with the Patriots," he says, "they wrote in all this language for how much I had to pay them back if I got hurt skiing. But I wasn’t gonna not ski, so I was able to find an insurance underwriter that would insure me just for the days that I ski — like, 25, 30 days of insurance a year."

It rarely snows in Walla Walla, and a recent freak storm that dropped snow and, a few days later, a slick sheet of ice, briefly shut down schools and businesses. It also made the Doubleback staff worry that one of their company vehicles — an old tan hand-me-down Suburban that Drew used to haul his family’s ski stuff in, and that his brother Adam drove for years — might not be able to make it over the rolling hills leading up to the production facility Doubleback leases. (It did, but barely.)

As the Doubleback team put together its first vintage, a 2007 Cabernet Sauvignon, it ran business operations out of a small condo and used the production facilities at another local winery, Leonetti. Now Doubleback has two estate vineyards, McQueen and Bob Healy. (The latter was cheekily named in honor of Drew’s late father-in-law, who liked to tease Drew that there was no real difference between fancy-schmancy wine and Two Buck Chuck.) There is also a big, airy tasting room on a downtown Walla Walla street corner, and the leased production facility a short drive from downtown. This spring, Doubleback will begin work on a 48.5-acre vineyard called Flying B, where they will also build a production space of their own as well as an on-site tasting room. The hope is that it will be a space worthy of the wine — like the flagship Cabernet Sauvignon — the label produces.

Walla Walla was struggling when Bledsoe was in high school, with the storefronts of its main drag — conveying a part–Wild West, part-midcentury feel — half-empty. These days, even under a rare coating of snow that glitters in the frigid January cold-front air, the area looks a whole lot like Sonoma: tasting rooms, farm-to-table restaurants, decor stores that sell antique furniture alongside bar stools fashioned out of wine barrels. Walla Walla has turned into a legitimate destination for wine enthusiasts, thanks in large part to Francesco and Rosa Leonetti.

Decades before Stu relocated from California to Washington to try his hand at raising cattle, the Leonettis emigrated from Italy and settled in Walla Walla, where they established a homestead farm in 1906 that featured chickens, hogs, a vegetable garden, and some grapevines. Their grandson, Gary Figgins, became fascinated by the winemaking process and began planting grapes of his own. When Figgins launched Leonetti Cellar in 1977, he put Walla Walla on the oenophile’s map. (You know a vineyard is good when its website states: "Leonetti Cellar does not a have a public tasting room and we do not accept appointments or offer tours" and touts a waiting list of three to four years just to get on the wine distribution list.)

Josh McDaniels (no relation!) says that he basically grew up on one side of the Leonetti land, and Bledsoe, who is close in age to Gary Figgins’s son Chris, grew up on the other. McDaniels, 28, is now Bledsoe’s chief winemaker at Doubleback, but he vividly remembers being just a fan as a kid. McDaniels also played football at Walla Walla High, and says that everything from the locker room to the tunnel out to the field featured reminders of Bledsoe. "He was basically a mythological figure," says McDaniels, who as a child stood in line at the Walla Walla Balloon Stampede to get Bledsoe, who had just been drafted by the Patriots, to sign his Washington State Cougars hat. But while Bledsoe was the mythological figure in McDaniels’s young life, Chris Figgins was the influential one. McDaniels knew Figgins from church, where the well-known winemaker, who had learned the craft from his father, Gary, was his youth-group leader. McDaniels routinely pestered Figgins with questions about everything from farming to fermenting to bottling. By the time Bledsoe returned to Walla Walla, McDaniels was quickly becoming Figgins’s protégé.

As Bledsoe had transitioned from young stud to seasoned vet in the NFL, he had also started to appreciate wine more than beer or whiskey, and he made two fun discoveries: Not only could he find bottles of Leonetti all the way in Massachusetts, but whenever he brought it to a dinner it was always the biggest hit. A trip to Napa Valley in the late ’90s made him appreciate all the facets of the process; he loved that it included farming and agriculture elements, but also involved marketing and business. When he retired in 2007 and decided to embark on a winemaking venture back in Walla Walla, he didn’t imagine that someone as high profile in the industry as Figgins would be available to help him out. But Figgins served as Doubleback’s initial consulting winemaker, producing the wine out of Leonetti Cellar. He also put into place an impressive succession plan. If the NFL has coaching trees, the wine industry has winemaker vines, and Figgins groomed McDaniels, who had been working with him at Leonetti in various capacities since he was a teen, to eventually take his place at Doubleback in 2015.

"What if this guy is an asshole?" McDaniels admits to initially wondering when he heard that Bledsoe would be starting his venture. (They do say that your heroes will only disappoint you.) Instead, upon his introduction to Bledsoe at Leonetti Cellar, McDaniels found that not only was he serious about the industry — this was not just some celebrity vanity side hustle — he was a really nice guy, and one with a surprisingly good palate.

Now, despite being several decades the junior of so many of his industry peers, McDaniels is in charge of Bledsoe’s winery operations. Wine Enthusiast named him one of "Washington’s game-changing winemakers." He oversees a growing array of Doubleback offerings that include the signature Cab, but also a Syrah, a rosé, and a juicy table red known as the Bledsoe Family Wine that got its start when Drew and his wife, Maura, would bottle excess wine at the production facilities and bring it home to drink with dinner.

McDaniels has the calm, assured air of someone who knows what he’s doing, and the rare gift of being able to explain nitty-gritty wine stuff in an accessible, understandable way, pulling basters of wine out of various barrels in the production facility to illustrate how certain variables, from time on the vine to the brand of barrel wood, impact the taste. The production facility has a room of barrels as well as a room of more newfangled equipment, from stainless steel vaults to concrete containers that look like giant eggs. It’s McDaniels’s job to do the research and development, to see which methods work and which blends taste best. "He’s young in years," Bledsoe says. "But he’s not young in experience. In some ways, there are similarities to my deal in New England: Chris [Figgins] is the renowned ‘rock star’ and Josh is the young kid getting in underneath him."

Bledsoe has two proudest wine moments: the first time he and Maura sat down for dinner, opened a bottle of Doubleback Cab, and liked it; and the time Doubleback cracked Wine Spectator’s 2010 Top 100 list. ("In the wine world you love to hate the critics," he laughs, "but when they give you a good score, it’s pretty cool.") Ask him about his proudest football moments, and he doesn’t mention his Pro Bowl seasons, or the way he turned the Patriots franchise around, or even the AFC championship game in Pittsburgh during that bittersweet Super Bowl–winning run, when Brady got injured in the second quarter and Bledsoe subbed in, threw a TD pass, and happily hoisted the Lamar Hunt Trophy. (He later said that his role in that win enabled him to wear his Super Bowl ring with pride.) Instead, he says: "I’m pretty proud that I never stayed down on the field, not ever. They never had to come and get me. Even the hit that ultimately allowed Tommy in the game — I got up and went back in the game the next series."

In interviews, Bledsoe sometimes points out that he’s not exactly Wally Pipp — who, the apocryphal story goes, sat out a baseball game with a headache, was replaced by some young pup named Lou Gehrig, and then became a punchline. Bledsoe’s career didn’t end when Brady replaced him; he went on to appear in another Pro Bowl after being traded to the Buffalo Bills in 2002 and later brought repeated late-game magic to the Dallas Cowboys in 2005. He remains friendly with Brady and maintains a great relationship with the Patriots, who inducted him into their team Hall of Fame in 2011.

But that narrative is hard to shake. His time in Dallas was also cut short by a young backup quarterback, Tony Romo. And this season, with Romo losing his starting job to Dak Prescott, the Patriots being the Patriots, and this being the 15-year anniversary of Bledsoe’s injury and Brady’s first Super Bowl win, Bledsoe has found himself fielding lots of questions about what it’s like: for Romo to watch Prescott, and for Bledsoe to watch Brady. He answers thoughtfully and patiently; he seems more reflective than resentful. He’s honest about how hard it was to lose his franchise quarterback status in New England, but he also seems to be at peace.

It helps that he barely has a free moment to overthink it. There’s lots of planning to be done regarding the groundbreaking of the new vineyard. Doubleback is a serious business for Bledsoe, and one of the things that makes him happiest is the way it’s really starting to come into its own, both financially and reputationally. This chapter of his life is still being written. Bledsoe is also a father of four, and his children have been slowly leaving the nest: His son John will play quarterback at Washington State in the fall, and another son, Stuart, is studying viticulture and playing lacrosse at Cal Poly.

What’s more, a series of winter storms has allowed Bledsoe to rack up the ski days this season. (He swears, by the way, that he didn’t start dating Maura, whom he first met at Washington State, just because her uncle Bill Healy — a former ski-trooper in the Army’s famous 10th Mountain Division — founded the ski mountain Mount Bachelor.) Recently, Mac joined his son and grandchildren in Montana to go skiing, and saw a familiar powderhound gleam in their eyes when they caught a glimpse of the fields of steep, untouched snow. He told them he’d meet them at the bottom. "I didn’t want to hold them back," Mac says, laughing. "I don’t want that to be my legacy."

There’s another story that Mac tells about a moment that transpired after the Patriots capped the 2001 season with a Super Bowl win but has its roots in that same high school sophomore season in which Drew bruised his liver. That year, an assistant coach, Mark Thompson, had tasked Drew and his Walla Walla teammates with coming up with a mantra that could define them. According to Mac, they took a few days to think about it and came back with the poem "The Guy in the Glass." Bledsoe hung a copy of it in his locker throughout his high school, collegiate, and professional career. A snippet of it reads:

For it isn’t your Father, or Mother, or Wife,

Who judgment upon you must pass.

The feller whose verdict counts most in your life

Is the guy staring back from the glass.

After Brady and the Pats upset the Rams to win that Super Bowl, Bledsoe went out to Montana, where he has a cabin. The next morning, Mac met up with him for a ski. He found Drew sitting outside, next to a fire pit, wearing his ski gear and drinking coffee and looking out at a nearby lake. "And I sat down," Mac says, "and said, ‘Son, you’ve been on a real roller coaster.’ And he said something very enlightening, and probably one of the things that I admired him most for, in his entire career."

Drew told his dad that he had showered that morning, and brushed his teeth, and stood in front of the mirror readying to shave. Retelling the story, Mac’s voice breaks. "I get a little emotional talking about it," he says. "But he said: ‘Dad, I looked in the mirror today and said, Ya know, I think I like that guy.’"