BOSTON — When it comes to being a sports fan, few, if any, have put money where their mouth is more than Dennis Drinkwater.

Super Bowls? The upcoming one in February will be his 50th … straight!

The Final Four? Almost all of them in the 1980s, mixed in with a few others.

The New York Giants? Didn’t miss a game — 250 straight, home and away — from 1986 to 2001.

The Masters, NBA Championships, Stanley Cup Finals and Kentucky Derby. Been there.

Of course, Drinkwater has the means to support his sports passions.

The businessman started with a local auto glass repair company in 1969, Giant Glass, and built it into a huge New England-based company headquartered in North Andover, later selling it to a national company, Safelite Auto Glass, in 2012.

But there is one particular sports passion, really one local team, that goes beyond “having means.”

Drinkwater might be the Red Sox’ No. 1 fan.

"There are Red Sox fans and there is Dennis Drinkwater," said Red Sox president Sam Kennedy. "He’s been part of Red Sox Nation going back to Teddy Ballgame and truly part of our family since the winter of 2001. We love him and consider him the karma king.  There is just no one better than 'The Drinks.'"

Drinkwater shot back.

“I appreciate that thought," he said about his place among fans. "But I don’t know about that."

True Red Sox fans sure do.

They couldn’t miss him if they tried. He’s the colorful guy with big hair who sits in the front row just to the left of the umpire.

He only misses a few games early each year, usually due to his Florida residency requirement.

But he never misses opening day, a streak started in 1960.

“There was one home opener when I was at the Final Four in Seattle, then went to Las Vegas. I remember sitting at the baccarat table telling the dealer, ‘I gotta go and catch a flight to Boston. I’ve got the opener in a few hours.’”

“I remember being at that game falling asleep with my head down and waking up,” said Drinkwater. “Those days are over for me.”

Drinkwater’s other big passion, the New York Giants, was a family thing. Growing up in Wakefield, Massachusetts, his family had connections as a distributor for Ballentine & Sons Brewing Co. in the New York/New Jersey area, a sponsor with the Giants. Drinkwater’s father was a big Giants fan and son soon followed.

“People always ask why I’m not a Patriots fan,” said Drinkwater. “I like the Patriots. I respect them. But I was a Giants fan before the Patriots were even created. People that know me know I don’t jump ship. I’m always committed.”

Drinkwater said the first game he ever attended was with his mom in 1951. But it was one player in Boston, Ted Williams, that caught his attention.

“Teddy Ballgame was the best,” said Drinkwater. “How could I not love him and the Red Sox. I was hooked very early on the Red Sox.”

He was hooked on the sport, too, playing in Wakefield High and Salem State University, both teams which he captained. and then for nearly two more decades in the famed Inter-City League.

Then he started and managed a semi-pro team, the Lawrence Giants.

“There is something about baseball for Drinks,” said retired former North Andover police officer Jack McEvoy, who attended Tuesday night’s controversial Game 4 at Fenway Park with Drinkwater. “He played the sport for so long. He knows so much about it. and then you add in the Red Sox and it’s a special connection.”

Drinkwater’s first season tickets were in the bleachers in 1978. He was in the bleachers for the Red Sox’ one-game playoff with the Yankees to make the postseason.

“Boy, that was a tough loss. Tough,” said Drinkwater. “That one still hurts, believe it or not.”

As his business boomed his ticket selection improved, getting four seats in the eighth row behind the Red Sox dugout.

Soon after the new Red Sox ownership group, headlined by John Henry, took over the team in December 2001, Drinkwater met with them about sponsorship.

He not only paid for a huge “Giant Glass” sign in the outfield and signs in other parts of Fenway Park, but he upgraded his seats, to where they are today.

“I’ll never forget it,’’ said Drinkwater. “It was a snowy day in February. I was one of the first sponsors with the new group. Sam Kennedy said ‘Pick out your seats.’ I took right behind home plate. I chose the four right there, in the front row. and they haven’t gotten rid of me since.”

Kennedy confirms most of Drinkwater's memory of that day.

"First of all, I grew up in Boston. But when I met Dennis he had a Boston accent I hadn't really heard before," said Kennedy. "Probably a North Shore thing.

"He told he he was interested in premium seats, and as luck would have it, we were expanding Fenway with the new dugout seats," noted Kennedy. "We started walking down the third base line and I went toward the dugout. And he said, 'No big boy, right here.' He was pointing behind home plate. We got there and he said, 'I want these four seats.' I told him, 'They're yours.'"

One of the highlights of watching a Red Sox game from Fenway is every few weeks a familiar face sits next to him.

Former Giants punter Sean Landetta, former Patriots and Giants assistant Charlie Weis, Giants vice president Chris Mara, Larry Lucchino, Lenny Clarke and famed comedian Greg Hoyt who portrays a “bad” Boston accent in the Sam Adams commercials are just a few of the names.

But there are two “Bobs” that drew a lot of publicity.

Former WBZ sportscaster Bob Lobel and an actor by the name of Robert “Bob” Redford.

“Bob Lobel has been to several games, one I’ll never forget,” recalled Drinkwater. “People were yelling his name between innings and he turns around and waves to them with both arms in the air. Next thing you know the reliever from the other team throws a pitch about 100 miles per hour over the catcher. and the ball hits the net, but also hit Bob in the back. He ended up having indentations of the net in his back it was so hard. I felt bad.”

Redford’s appearance at the Salem State Speakers Bureau, which Drinkwater sponsored, led to him agreeing to see a Red Sox-Yankees game in 2005 when the rivalry was red-hot.

“He just loved everything,” said Drinkwater. “We walked around the park, everywhere. He wanted to see it. He sent me a nice note and I put it in a picture frame. The funny thing is he wanted to be called ‘Bob.’ So that’s what I called him.”

While the championships and the championship runs have been memorable — including his traveling to St. Louis in 2004 and Colorado in 2007 — he said it’s been the relationships he’s forged the last two decades in particular that make this experience even better.

Two of his favorite players, on and off the field, have been David Ortiz and Josh Beckett.

“David’s funny,” said Drinkwater. “He said one day, ‘How do you come to all the games?’ I said, ‘Because I love it! That’s why.’”

Most recently, his guests in the Drinkwater seats have been close friends and family, including his wife Jacqueline, son Dean, Dean’s kids Grant Drinkwater, 16, and Chase Drinkwater, and daughter Nicole Lewis, and her kids Jake, 11, and Celia, 14, at Bishop Fenwick.

“Family is everything to me. Everything,” said Drinkwater. “I honestly have the most fun with them. They love it. My granddaughter is a maniacal fan. She’s driving down with me on Sunday to see the Giants in East Rutherford (N.J.).”

As for the 2021 Red Sox, which play Friday night in Game 6 after two tough defeats, Drinkwater said: “Relax!”

“Don’t you dare give up on them,” said Drinkwater. “They have bounced back all year. I love this team. I really do. They have given me so much joy. I believe they win game six and who knows about game seven?

“What makes me happiest this year is seeing the Red Sox fan base,” said Drinkwater. “It hasn’t been covered enough. The Red Sox fans are back more than ever. The Wild Card game against the Yankees was the loudest I’ve ever heard here. I’m serious. They are all ages, women, kids, old people like me. Red Sox fans are the best.”

It takes one to know one.

You can email Bill Burt at

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