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Former Heisman Trophy winner Doug Flutie fondly remembers late Red Sox pitcher Tim Wakefield

Flutie spoke during the Travelers Celebrity Pro-Am Wednesday in Connecticut, an event that Wakefield frequented.
Credit: FOX61
Late Red Sox All-Star Tim Wakefield is remembered fondly by former Patriot Doug Flutie

CROMWELL, Conn. — Former Heisman Trophy-winning quarterback Doug Flutie fondly remembered his late friend Tim Wakefield during the Travelers Celebrity Pro-Am at TPC River Highlands in Cromwell, Conn. on June 19.

Wakefield, the former All-Star pitcher and two-time World Series champion who spent 17 seasons with the Boston Red Sox, passed away on Oct. 1, 2023, at age 57 after battling brain cancer. Wakefield often came to Connecticut for the celebrity pro-am, and Flutie donned a #49 Red Sox jersey and hat in honor of his friend as he teed off on Wednesday.

RELATED: Tim Wakefield, who revived his career and Red Sox trophy case with knuckleball, has died at 57

Flutie spoke highly of the knuckleballer in between rounds. He said Wakefield introduced him to the Travelers Championship.

“Coming to this tournament, I miss seeing Tim and hanging out for the week. He was special to everyone he met. I’ve never heard a bad word about him from anybody,” Flutie said. “Just hand in hand, he was a first-class individual.”

Flutie recalled playing many rounds of golf with Wakefield and sportscaster Chris Berman. Flutie and Wakefield spent many days together as they lived near each other in Florida. He considered Wakefield and his wife Stacy close friends; Stacy lost her battle with pancreatic cancer in late February.

RELATED: Stacy Wakefield dies less than 5 months after her husband, World Series champion Tim Wakefield

“The things he did with the Red Sox were absolutely amazing. The things he did off the field are even more amazing. We really miss Tim and Stacy both,” Flutie said.

Flutie commended Wakefield for contributing to the Doug Flutie Jr. Foundation for Autism, named for Flutie's son. Wakefield was also involved with several charities during and after his career. 

Flutie and Wakefield each enjoyed long careers as professional athletes. After rising to fame at Boston College and winning the Heisman Trophy in 1984, Flutie got his start in the U.S. Football League in 1985 before spending four seasons in the National Football League split between the Chicago Bears and New England Patriots.

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In 1990, Flutie traveled north of the border, where he starred in the Canadian Football League for multiple teams, becoming a champion and one of the league’s greatest players. In 1998, he returned to the NFL and made a Pro Bowl appearance with the Buffalo Bills. Flutie’s NFL career lasted through 2005; he retired with the New England Patriots, one of the teams he started his pro career with.

Known for his knuckleball, Wakefield was a converted first baseman who made his Major League Baseball debut with the Pittsburg Pirates in 1992. After several up and down seasons, Wakefield was released by the Pirates and signed with the Red Sox for the 1995 season, after which he was named the American League’s Comeback Player of the Year.

Wakefield became a legend and fan favorite with the Red Sox during his 17 seasons in Boston, winning two World Series championships. He made an All-Star appearance in 2009 before retiring after the 2012 season. While Wakefield was known as a starter, Flutie remembered his time spent in the bullpen winning fans over.

“Tim’s special,” Flutie said. “He won the hearts of Red Sox fans with what he did out of the bullpen more, winning the World Series (twice) and being part of those teams, and off the field all the things he’s done locally were just amazing.”

Flutie recalled how Wakefield was the “glue” guy at all the tournaments and events they did together. When Flutie was unfamiliar with those around him, Wakefield always made him feel at home.

“It’s like I always felt on the outside because it was mostly Red Sox guys, and I always felt like an outsider with that group, but Tim would text, get everybody (coordinated), and he was that guy that brought everyone together all the time and made me comfortable around all the former Red Sox guys and all the current guys too,” Flutie said.

When asked about his Wakefield jersey and hat, Flutie said wearing them were a no-brainer. It was just a matter of which Wakefield jersey to wear.

“It was just which one,” Flutie said. “There was a commemorative jersey that is black, but I didn’t know if people would recognize it, so I wore the white, but I don’t think I’ve taken this 49 hat off since (he passed).”

In Cromwell, the Travelers Championship is right around the corner as some of the top golfers in the world compete on the PGA Tour event for a $20 million purse. The action begins bright and early on Thursday morning.

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Dalton Zbierski is a digital content producer and writer at FOX61 News. He can be reached at dzbierski@FOX61.com

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