PlumpJack Winery's story began in 1992 with the opening of a modest wine store in San Francisco's Cow Hollow/Marina neighborhood, known as PlumpJack Wine & Spirits. Founded by Gavin Newsom, the store was designed to create a welcoming space where people could explore and discover wines in a friendly, approachable setting.

The name "PlumpJack" was inspired by one of Shakespeare's most memorable characters, Sir John "PlumpJack" Falstaff, a fun-loving, irreverent figure known for his unbreakable bond of loyalty with Prince Hal (Henry V), shared over many goblets of wine at the local tavern. Embracing this spirit of camaraderie and enjoyment, Newsom, along with acclaimed composer and philanthropist Gordon Getty, envisioned a winery that would embody the essence of Falstaff's character. This vision came to life when they acquired a historic 42-acre estate in the heart of Napa Valley, an area renowned for producing dynamic, long-lived wines that capture the essence of Oakville, with a history dating back to 1881.

The property had changed hands over the years, eventually being acquired by James and Anne McWilliams in 1974. In 1995, the McWilliams received a proposal to revive winemaking at the historic estate, leading to the creation of PlumpJack Estate Winery. The winery was founded with a commitment to crafting high-quality wines that celebrated the land while remaining approachable.

A pivotal moment in PlumpJack's history came in the 1990s when the wine industry faced the growing problem of cork taint, or trichloroanisole (TCA), which caused undesirable flavors in bottled wines. Unwilling to compromise on quality, Getty and General Manager John Conover took a bold step toward innovation. PlumpJack Estate Winery pioneered the use of alternative closures for luxury wines, introducing screw caps with the flagship 1997 Reserve Cabernet Sauvignon. This move eliminated the risk of TCA while ensuring bottle consistency and longevity. To this day, PlumpJack bottles its Estate and Reserve Cabernet Sauvignons 50% under screw cap and 50% under cork as part of a long-term experiment.

In 2012, Winemaker Aaron Miller joined the team, continuing the legacy of producing elegant wines that honor the Oakville Estate Vineyard. Under Miller's leadership, PlumpJack achieved significant milestones, with the 2013, 2015, and 2016 Reserve Cabernet Sauvignons earning perfect 100-point scores from Robert Parker’s Wine Advocate—a testament to the winery's dedication to quality and approachability.