The Prisoner is one of Napa’s most popular wines. It also glamorizes something ugly: incarceration

There is no winery in Napa Valley like the Prisoner Wine Co. Amid all the

There is no winery in Napa Valley like the Prisoner Wine Co.

Amid all the valley’s visually redundant wineries, the Prisoner stands out as starkly modern — a sleek, horizontal monolith on Highway 29 in St. Helena. The surrounding Tuscan villas, faux chateaux and palatial farmhouses feel prudish by comparison. Inside the Prisoner’s tasting room, one wall is covered in long, dangling shackles. Customers sip flights of wine while surrounded by metal bookshelves held up by prison cell-like bars.

It’s one of Napa Valley’s most prosperous attractions, and its products, the various Prisoner Wine Co. bottles, are among the country’s best-selling wines. Since the first Prisoner red blend debuted 21 years ago, it has enjoyed an unparalleled level of success. It’s the third-best-selling wine over $25 in the U.S., according to data analytics firm Information Resources Inc., and the top-selling red blend in that price range.

The Prisoner is arguably one of the most influential wines in modern history: It has spawned a generation of copycat brands, lining grocery shelves with gothic-looking red blends such as 19 Crimes and Bodyguard. What this winery does matters — its choices and successes reverberate throughout the industry.

The Prisoner Wine Co. tasting room in St. Helena, which opened in 2018, two years after the corporation Constellation purchased the brand.

Preston Gannaway/Special to The Chronicle

Yet one of the brand’s core elements has taken on a new gravity within the context of a growing conversation around race and criminal justice: its use of imprisonment as a marketing aesthetic.

The wine itself has always depicted captivity; the flagship red blend’s label shows a twisting, tortured figure constricted by bars and chains. Since a new owner, Constellation Brands, acquired the company in 2016, and especially since opening the tasting room in 2018, the brand has leaned further into that imagery. The tasting room decor has featured metal skeletons, ball-and-chain sets and braided ropes hanging from the ceiling.

Those symbols connect the Prisoner to the national conversation around mass incarceration and systemic racism, in ways that have become difficult to ignore. Those may sound like bigger concerns than any winery should have to contend with, yet during the last year and a half, many California wineries have faced complicated issues courageously, attempting to address the fact that the wine industry has historically excluded people of color from positions of power, and alienated them as customers.

The winery is aware of this dynamic. Its new general manager, Bukola “Bukky” Ekundayo, who joined in August, said she wants to use the winery’s platform to advocate for prison reform; the company has made some donations to the cause already.

The question now is whether Ekundayo and her colleagues can pull off this big ask: transforming the Prisoner from a wine that appears to fetishize incarceration into one that takes a stand against it.


Left: Bukola "Bukky" Ekundayo, who became the Prisoner Wine Co.'s general manager in August, says there are plans to invest more in the brand's social-justice activities. Right: One of the Prisoner's spin-off brands, Unshackled.

Left: Bukola “Bukky” Ekundayo, who became the Prisoner Wine Co.’s general manager in August, says there are plans to invest more in the brand’s social-justice activities. Right: One of the Prisoner’s spin-off brands, Unshackled.

Preston Gannaway/Special to The Chronicle

The Prisoner wine first emerged during a crucial, transitional moment in Napa Valley — and in many ways, defined a new era.

In 2000, a young Napa winemaker, Dave Phinney, was working on a label he’d started two years earlier called Orin Swift. At the end of harvest, he had some inconvenient leftovers on his hands. There was some Cabernet Sauvignon that he decided wasn’t good enough for it. And there was some Zinfandel that, no matter how hard he tried, just wouldn’t ferment all the way — it still had some unfermented sugar left in it.

“To me, any (residual sugar) was essentially a flawed wine,” Phinney said. Then he had an idea: blend the sweet Zinfandel with the dry Cabernet to lessen the overall sugar level. It was a weird thing to do, according to conventional winemaking wisdom. Wines, back then, were blended according to templates established by European wine regions centuries ago. You could make a Bordeaux blend (Cabernet Sauvignon, Merlot, Cabernet Franc). You could make a Rhone blend (Grenache, Syrah, Mourvedre). But to mix and match felt sacrilegious.

Still, Phinney figured, what the heck.

There had been some precedent for freeform red blends decades earlier, with jug wines like Gallo Hearty Burgundy. But that was cheap plonk. When Phinney released the Prisoner, he sold it for $25 — audaciously expensive back then for a wine that couldn’t summon the cachet of Cabernet Sauvignon.

When it came time to give this kitchen-sink blend a name, Phinney was sitting at his desk, he said, staring into space, hoping for inspiration. Hanging on the wall was an etching by the Spanish artist Francisco de Goya, a treasured gift from his parents for his 13th birthday. It showed a man in shackles, his face obscured by shadows. The wrenching, emotional image had always spoken to him, he said. Phinney reproduced that image for the wine’s label and called it the Prisoner.

Almost immediately, the wine was a sensation.

“There was nothing like it at the time,” said Bill Hayes, the wine buyer for BevMo. “It was allocated. We couldn’t keep it in stock.” The moody label stood out on the shelves — today, they’d call it “disruptive” — among bottles that mostly just depicted a winemaking family’s name in cursive.

The wine was such a force that it singlehandedly created a new genre in the U.S. wine market: the red blend. “People started addressing it as if it was its own varietal,” said Kimberly Jones, a Napa wine seller who sold the Prisoner from 2003 to 2014. “There’s Cab, there’s Merlot, there’s the Prisoner.”

It also instantly engendered intense debate. Those who loved it really loved it: The Prisoner was luscious, velvety, gratifying, just sweet enough, a masterful execution. Wine snobs loved to hate it, objecting to its ultra-ripe flavors, writing it off as saccharine.

“It was so polarizing,” Jones said. “You’d hear one person say it’s the best wine they’ve ever tasted, then the next would say they won’t drink it.”

Phinney made only 385 cases in 2000, and so had to ramp up quickly. He took advantage of the fact that the other winemakers in Napa were competing to get ever-more-desirable Cabernet Sauvignon grapes. He went in the opposite direction. Growers with fields of Merlot, Zinfandel, Petite Sirah, Charbono and other less popular red grapes were eager for buyers, and Phinney could get their fruit for cheap. He wasn’t tied to any particular formula, so the Prisoner blend could change every year depending on what was available.

Big wine conglomerates took notice. Many of them rushed to bring their own ripe-tasting red blend with an edgy label to market. Today, popular red blends like 19 Crimes, Bodyguard, Tall Dark Stranger and Freakshow “are all here because of what the Prisoner started 20 years ago,” said BevMo’s Hayes.

By 2010, when Phinney sold the Prisoner to Huneeus Vintners, the powerful Napa dynasty that owns Quintessa, Faust, Flowers and other wineries, production had grown to 85,000 cases. The $40 million price tag may have seemed like a lot, but it would pale in comparison to the $285 million that Constellation would pay Huneeus for it six years later.

A wine tasting at the Prisoner Wine Co., featuring a bottle holder made from chains.

A wine tasting at the Prisoner Wine Co., featuring a bottle holder made from chains.

Preston Gannaway/Special to The Chronicle

Under Constellation’s ownership, the Prisoner has transformed from wunderkind to behemoth, with a near-constant churn of new product lines. In addition to the original red blend, which now sells for $50, there’s a Cabernet Sauvignon, a Pinot Noir and a Chardonnay. In September, the company announced it would build out a new brand around its Saldo Zinfandel, releasing what Ekundayo described as “less-popular, discoverable varieties” like Chenin Blanc.

Sales have grown by 550{2099cc1b97d4d5af6b378c51833a8c0e04bb5da587377bd6b2cb473fa3104767} since Constellation purchased the Prisoner in 2016, according to Ekundayo. The wine itself is more visible than ever, its bottles a frequent accessory in artsy influencers’ sponsored posts. Within the last year, “Saturday Night Live” star Chloe Fineman has promoted the Prisoner’s availability on the delivery app Drizly. Industry analysts point to it as the rare tasting room in Napa Valley that’s actually attracting Millennial customers, a demographic many wineries are failing to reach.

Annual case production is in the ballpark of 250,000, Constellation confirms, and the tasting room was drawing 2,500 visitors per month pre-pandemic. (The average Napa tasting room saw 1,372 per month in 2019, per Statista.) Current visitation rates are almost back to that peak.

Indeed, during a trip to the tasting room this fall, it was swarming with groups of well-dressed people in their 30s and 40s, swirling glasses of Saldo Zinfandel and Headlock Charbono. Many piled into limousines in the parking lot to head to their next tasting.

There seems to be nothing that can stop the Prisoner from its astronomical climb. The brand is a cornerstone of Constellation’s overall strategy around reorienting toward higher-end wine. Earlier this year, it sold off 30 of its lower-priced brands to Gallo, for $810 million, in order to invest more in its expensive wines like the Prisoner.

But when it comes to branding, the visual metaphors of imprisonment feel more potent than ever. It has continued to play up the theme with new labels like Unshackled, Derange, Eternally Silenced and Blindfold. A Chardonnay called the Snitch depicts a mugshot with most of the person’s face torn out. The tasting room’s gift shop sells souvenirs like a bottle holder made from chains and pottery with decorations that suggest punishment tools.

Its original winemaker never intended for the Prisoner to be so deeply invested in the imagery of imprisonment — nor, indeed, is that what Francisco de Goya intended in his etching.

The title of the artwork, Ekundayo said, was “The Captivity is as Barbarous as the Crime.” It’s sometimes translated slightly differently, but the gist is correct. “The label itself is a commentary on the injustice of war and imprisonment,” she said.

Whatever the intention, the end result of the decorative shackles behind the bar is unnerving: One of Napa Valley’s most popular exports — and one that speaks to the very identity of California wine — hinges on glamorizing the incarceration aesthetic.


The Prisoner is one of Napa Valley's most popular tasting rooms. Pre-pandemic, it saw about 2,500 visitors per month; the average tasting room in the area sees closer to 1,400. Here, wine educator Roberto Cromeyer talks to Colin Herold (from left), Charles Robin and Kathryn Robin.

The Prisoner is one of Napa Valley’s most popular tasting rooms. Pre-pandemic, it saw about 2,500 visitors per month; the average tasting room in the area sees closer to 1,400. Here, wine educator Roberto Cromeyer talks to Colin Herold (from left), Charles Robin and Kathryn Robin.

Preston Gannaway/Special to The Chronicle

At the same time as Constellation has emphasized the Prisoner’s lurid imagery, the national debate around mass incarceration has grown more urgent. More people are in prison in the U.S. than in any other country, and people of color — particularly Black men, by a factor of 5, and Latino men, by a factor of 1.3 — are disproportionately represented in the prison population, according to the Sentencing Project. Despite laws requiring basic rights for inmates, conditions at many jails and prisons remain inhumane.

Though these issues aren’t new, there’s more widespread awareness of them. Those who visit the Prisoner’s tasting room or see it promoted on Instagram, though, aren’t being prompted to consider any of these serious implications. They’re not reminded that at one point last year, people in California prisons died of COVID-19 at twice the rate of the general population due to overcrowding, and they’re not reminded that conditions were once so bad that suicide rates were 80{2099cc1b97d4d5af6b378c51833a8c0e04bb5da587377bd6b2cb473fa3104767} higher in state prisons here than elsewhere in the country.

A $100 wine called Derange does little to signal to drinkers that incarcerated people often don’t receive appropriate mental health care. Just in August, the federal government found that the Central Coast’s San Luis Obispo County Jail violated the constitutional rights of its inmates, including the Eighth Amendment’s prohibition of “cruel and unusual” punishment. There, the Justice Department found, the jail was subjecting some to “excessive uses of force” and “failing to provide adequate medical and mental care.”

For people advocating for change in the prison system, imagery like the Prisoner’s impacts the work they’re able to do. “Titles like ‘the Prisoner,’ we feel, hinder our ability to create sound policy,” said James King, campaign manager for Oakland’s Ella Baker Center for Human Rights, which advocates for prison reform. “Anything that reduces a person to their incarceration status or uses tropes like shackles or razor wire is harmful to a community that is struggling to be seen. That really creates a subconscious othering of people and leads to ideas like, ‘We have to be tough on crime.’”

It’s possible to be a consumer with a conscience these days, King said, checking the values of businesses we patronize. The apparent obliviousness of the Prisoner’s many customers to its imagery underscores the wine industry’s deep racial disparities. Only 11{2099cc1b97d4d5af6b378c51833a8c0e04bb5da587377bd6b2cb473fa3104767} of U.S. wine drinkers are Black, according to Nielsen Spectra data, while 70{2099cc1b97d4d5af6b378c51833a8c0e04bb5da587377bd6b2cb473fa3104767} are white, ratios that echo the racial disparities in the prison population

“If you are drinking a wine called the Prisoner, the burden falls upon you to take the time to know what it is you are supporting,” said King. “What are you doing to understand imprisonment, to see who’s actually being imprisoned in our state, and to look to see what harm is being caused?”

Even Phinney objects to the way Constellation has emphasized the prison theme so literally. “It’s the exact opposite of what we were doing,” he said. “To me it was a story about the gift from my parents.” The etching still hangs in his living room.

Clockwise from top left: Pottery by Napa artist Amanda Wright for sale at the Prisoner's gift shop; a coaster shows a mugshot with a man's face erased, the same image that appears on the company's Snitch Chardonnay; bottles of Prisoner wines, including the original flagship red blend, second from right.

Clockwise from top left: Pottery by Napa artist Amanda Wright for sale at the Prisoner’s gift shop; a coaster shows a mugshot with a man’s face erased, the same image that appears on the company’s Snitch Chardonnay; bottles of Prisoner wines, including the original flagship red blend, second from right.

Preston Gannaway/Special to The Chronicle

Ekundayo is cognizant of these optics — and said the winery is working toward human rights goals, not against them. Although she would not disclose a total dollar amount, Ekundayo said that the Prisoner has donated to social justice organizations, including a joint $10,000 donation with Miami Heat player Moe Harkless to the Equal Justice Initiative, Bryan Stevenson’s nonprofit that provides legal counsel to the underprivileged.

A more robust set of commitments is in the works, she said. She plans to announce the company’s involvement in “much bigger programs” related to human rights within the next few months.

Ekundayo also wants to emphasize the viticultural significance of Prisoner. “When you look at the early history of Napa,” she said, “the Prisoner is really tapping into that.” In the 19th century, many vineyards were scattershot plantings of Zinfandel, Charbono, Petite Sirah and other grapes, beloved by the immigrants who planted them but largely dismissed by the contemporary wine establishment. The Prisoner, Ekundayo pointed out, is still one of the few wineries that produces a Charbono.

In fact, in the process of creating the wine, and using those unloved grape varieties, Phinney probably kept a lot of old-time farmers in business who might have otherwise struggled.

“He was rescuing a lot of vineyards — buying grapes that no one else wanted to buy,” said Jones, the wine seller. “He would see an abandoned vineyard and go try to find the owner. No one else had the guts to make a Zin-Petite Sirah blend from neglected vineyards.”

Ekundayo said that portraying the Prisoner as fetishizing imprisonment is misguided. The key to understanding it, she said, lies with the story behind the label’s original artwork. Visitors to the winery, however, are probably more likely to focus on the shackles hanging in its tasting room.