Drew Bledsoe and Wife Maura Have Been Married 28 Years and Make Award Winning Wine

“You have more rings than I do, but I’ve experienced a couple of things that you will never experience,” joked Drew Bledsoe.

Brandon Charles - Author
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Published May 6 2024, 4:50 p.m. ET

Early in The Greatest Roast of All Time former New England Patriots quarterback Drew Bledsoe got in one of the best jokes about his successor, Tom Brady. Not necessarily attacking but just pointing out two basic facts, Drew had a poignant observation about two of very few things Tom never had and will never have.

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“Hey look, buddy, you have more rings than I do, but I’ve experienced a couple of things that you will never experience,” began Drew, “The feeling of being the number one overall draft pick in the NFL and a 28th wedding anniversary. It was yesterday.”

Tom Brady and Drew Bledsoe in 2024
Source: Getty Images
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Drew Bledsoe and his wife have been married for 28 years

The best jokes are the realest. Drew was drafted number one overall in the 1993 NFL Draft, and he and his wife Maura Healy have been married since 1996. The two met while both were students at Washington State in the early 1990s. 30 years after college, the couple now reside back in Washington state.

Source: Instagram @drewbledsoe
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Living well is the best revenge. But wine is also nice.

While Drew only has one Super Bowl ring, largely due to Tom Brady's play, the former QB had a pretty great career after the Pats, playing for both the Bills and Cowboys. Once he got off the gridiron he got in the grape fields. After retiring from the NFL in 2007, Drew and wife Maura opened the Doubleback Winery along with Chris Figgins. The place is still in operation and doing quite well. The About page on the Doubleback site explains how the winery came about.

“Upon his retirement from the NFL in 2007, Drew Bledsoe 'doubled back' to his hometown of Walla Walla, Washington to realize a long-held dream. Drew and his wife, Maura, purchased a piece of property on the southern edge of the Walla Walla Valley AVA and subsequently launched Doubleback as an estate-focused winery with the goal of crafting America's best Cabernet Sauvignon in an elegant, true-to-varietal way."

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Drew and Maura Bledsoe
Source: Bledsoe Family Winery

Unlike a lot of professional athletes, Drew saw past his playing career when thinking about life without wearing a helmet. "Drew had long been planning for this moment during his years playing football and success came immediately as the very first vintage earned a spot in Wine Spectator's Top 100 List.”

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In addition to Doubleback, the family also has the Bledsoe Family Winery and Bledsoe|McDaniels. From the Bledsoe Family Estates about page, “The nationally acclaimed Cabernet Sauvignon of Doubleback, accessible varietals of Bledsoe Family Winery, and boundary-pushing Pinot Noir and Syrah of Bledsoe|McDaniels all showcase our commitment to exploring the full potential of our land to produce authentically representative American luxury wines.”

In addition to making wines, the Bledsoes have made sons John Bledsoe, Stuart McQueen Bledsoe, Henry Bledsoe, and daughter Healy. According to Drew’s Instagram, son Stuart recently got engaged to girlfriend Shelby Collins.

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Source: Instagram @drewbledsoe

All of the boys followed in dad's football steps, played football at Summit High in Oregon. Daughter Healy is also an athlete, currently playing basketball for Colorado College.

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