Dennis Drinkwater Net Worth | Celebrity Net Worth

What is Dennis Drinkwater’s net worth?

Dennis Drinkwater is an American businessman who has a net worth of $10 million. Dennis Drinkwater is an American entrepreneur best known as the co-founder of Giant Glass, a leading auto-glass repair business in New England, and as an iconic Boston Red Sox superfan. Over a career spanning decades, Drinkwater built Giant Glass into Massachusetts’ top auto-glass company through savvy marketing and customer service, while also becoming a fixture at Fenway Park thanks to his unwavering support for the Red Sox. With his signature presence in seats directly behind home plate at every home game since the early 2000s, Drinkwater has achieved local fame for never flinching at foul balls and for his enthusiastic yet humble fandom.

Early Life and Education

Dennis Drinkwater was born and raised in Massachusetts. He developed an early passion for baseball and the Red Sox, recalling that “I was hooked very early on the Red Sox.” In his youth, he not only cheered for the game but also played it: Drinkwater was a talented player at Wakefield Memorial High School and at Salem State University, captaining both teams during his tenure. He graduated from Salem State in 1967, earning a degree that helped equip him for his future business endeavors. Decades later, Salem State recognized his achievements by awarding him an honorary Doctor of Humane Letters in 2012. This honor underscored his contributions as an alumnus and business leader in the community.

Giant Glass

In the late 1970s, Dennis Drinkwater co-founded Giant Glass (along with business partner Lance Cramer) and set out to fill a niche in fast, reliable auto glass repair and replacement. Starting as a single local shop, Giant Glass steadily expanded under Drinkwater’s leadership.

By the 2000s, it had grown to multiple locations across Massachusetts and had become the state’s largest and most successful auto-glass repair company.

Drinkwater’s marketing strategy was a key to this success. Giant Glass became a household name in New England thanks to its memorable jingle and telephone number – 1-800-54-GIANT – prominently featured in its advertisements. This catchy number, which spelled out the company name, proved hugely effective. It was even said to be “the most recognizable jingle in the history of New England media,” reflecting how deeply it penetrated the local consciousness.

The company’s aggressive advertising included billboards, radio spots, and sponsorships that kept the Giant Glass name highly visible. Notably, Giant Glass became a prominent advertiser at Boston’s Fenway Park, with its logo and name appearing on signage and broadcasts during Red Sox games. This close association with the beloved baseball team not only boosted the company’s profile but also foreshadowed Drinkwater’s own deepening connection to the Red Sox.

Safelite Acquisition

After over three decades at the helm of Giant Glass, in late 2012, Drinkwater and his partner Lance Cramer agreed to sell Giant Glass to the national chain Safelite for an undisclosed sum. The deal closed in early 2013. At the time of the sale, Giant Glass had 54 employees, five locations around the Boston area and a fleet of 30 mobile service vans.

Drinkwater and his partner continued to oversee operations post-acquisition, ensuring a smooth transition. The sale marked the culmination of Drinkwater’s business career – transforming a small startup into an industry leader that attracted a major acquisition – while allowing him to focus more on his other passions and community engagements.

Boston Red Sox Superfan

Beyond business, Dennis Drinkwater is celebrated for his role as one of the Red Sox’s most dedicated fans. In fact, many consider him the team’s number-one fan – a title he humbly downplays. (“I appreciate that thought, but I don’t know about that,” he said when asked about the moniker.)

Starting in 2003, Drinkwater made it a personal mission to attend virtually every Red Sox home game at Fenway Park. He is known for sitting in what is arguably the best seat in the stadium: a front-row spot directly behind home plate.

One of the most famous aspects of his persona is his unflinching reaction to foul balls. Although a protective net is in place, most spectators reflexively duck or flinch when a foul ball rockets back toward the seats. Not Dennis Drinkwater – he sits serenely, often barely blinking as balls hit the screen in front of him. A montage of these moments, showing his “zen-like focus and calm” in the face of screaming line drives, went viral among Red Sox fans.

It’s all part of what makes Drinkwater an endearing figure at Fenway. Fans seated nearby have reported that he’s friendly and approachable, and he often greets those around him while remaining intensely focused on the game.

Personal Life & Real Estate

Dennis and his wife Jacqueline split their time between Ipswich, Massachusetts, and Miromar Lakes, Florida. They paid $1.1 million for their home in Ipswich in January 2004. They have listed this home for sale a number of times over the years and have not sold it as of this writing. They bought their Florida home in January 2024 for $2.6 million.