Kenny Chesney Pays Tribute To Beloved Red Sox Pitcher, Tim Wakefield: ‘I’m Sure Gonna Miss Him’

Chesney remembered his “pal” and recalled the time that Wakefield threw battling practice to him in 2004.


Lauren Jo Black

| Posted on

October 3, 2023


1:33 pm

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Tim Wakefield, Kenny Chesney; Photo Courtesy Facebook

Kenny Chesney is mourning the loss of his friend, Tim Wakefield, a former right-handed knuckleball pitcher who played for the Boston Red Sox. 

The country superstar shared a touching tribute to Wakefield, who passed away on Sunday, October 1, 2023, after a brief battle with brain cancer.

“Rest In Peace Pal”

“A very tough time for Red Sox Nation and @noshoesnation. Goodbye to my friend Tim Wakefield who I shared a lot of laughs with,” Kenny Chesney wrote on social media alongside photos of him with Wakefield and other Red Sox players. “Tim threw batting practice to me and a few friends at @fenwaypark in 2004. He came to countless shows over the years and I’m sure gonna miss him. Rest in peace pal.” 

Kenny Chesney shares a deep connection with the city of Boston, where Wakefield played. He has not only visited Fenway Park several times, but Chesney has also headlined Gillette Stadium in Foxboro, Mass. a whopping 21 times. 

Passed Away On Oct. 1

Tim Wakefield was just 57 at the time of his passing. According to ESPN, Wakefield’s former teammate Curt Schilling disclosed his illness without consent during a podcast days before his passing. While the Red Sox has mentioned Wakefield was ill, the organization did not elaborate in an effort to provide Wakefield and his family with privacy. 

According to, Wakefield underwent surgery “a couple of weeks ago” to attempt the fight the “aggressive cancer” he was battling. 

“Hearts Are Broken”

The Red Sox announced his death on Sunday.

“Our hearts are broken with the loss of Tim Wakefield. Wake embodied true goodness; a devoted husband, father, and teammate, beloved broadcaster, and the ultimate community leader,” a social media from the team reads. “He gave so much to the game and all of Red Sox Nation. Our deepest love and thoughts are with Stacy, Trevor, Brianna, and the Wakefield family.”

His death shook the sports community and the team. 

Boston Red Sox Tribute Tim Wakefield; Photo Courtesy Twitter
Boston Red Sox Tribute Tim Wakefield; Photo Courtesy Twitter

He Was Remember As An Athlete And Friend

“It’s one thing to be an outstanding athlete; it’s another to be an extraordinary human being. Tim was both,” Tom Werner, Red Sox chairman, shared in a statement from the team. “I know the world was made better because he was in it.”

“We lost a brother, a teammate, a family member. One of the best teammates I ever had. … Of all the guys I played with, nobody wore his jersey with more pride than Tim Wakefield,” Alex Cora, Wakefield’s ex-teammate and Red Sox Manager.  

Following his passing, tributes to the knuckleballer continued to pour in. 

“We are deeply saddened by the loss of Tim Wakefield, one of the most unique pitchers of his generation and a key part of the most successful era in the history of the Boston Red Sox,” Rob Manfred, MLB Commissioner,  said in a statement. “Tim’s knuckleball allowed him to excel as a rookie with the Pittsburgh Pirates in 1992. In 1995, he began a 17-year tenure in Boston, where he made a mark that will be remembered forever. Tim was more than just a versatile and reliable All-Star pitcher, a highly respected teammate, and a two-time World Series Champion. In 2010, Tim was named the Roberto Clemente Award winner for the dedicated work he and his family did serving the communities of New England.

“On behalf of Major League Baseball, I extend my deepest condolences to Tim’s family, his friends and teammates across the game, and Red Sox fans everywhere. We will continue to support our partners at Stand Up To Cancer in the memory of Tim and all those who are in the fight against this disease.”

Leaves Family Behind

Survived by his wife Stacy, son Trevor, and daughter Brianna, Wakefield, a key member of two Boston World Series championship teams, recorded 200 Major League wins, with 186 of those coming in a Red Sox uniform, ranking him just below Cy Young and Roger Clemens, both with 192 wins for the team.

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Lauren Jo Black

Written by

Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.