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.

By

Lauren Jo Black

| Posted on

October 3, 2023

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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 MLB.com, 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 is a longtime country music journalist, editor, host, and media personality whose work has helped shape the conversation around country music for nearly two decades. As the current Editor-in-Chief of Country Now, she has become one of the genre’s most respected voices, interviewing hundreds of country music’s biggest stars, including Dolly Parton, Garth Brooks, Reba McEntire, Shania Twain, Randy Travis, Luke Bryan, Carrie Underwood, Blake Shelton, Luke Combs, and countless others. Over the course of her career, Black’s written work and interviews have reached billions of country music fans worldwide. A 2009 graduate of the University of Central Florida, Black began her career by founding Country Music Is Love, one of country music’s earliest independent digital publications, which she later sold to a major record label in 2015 before it was rebranded as Sounds Like Nashville. She then served as the publication’s Editor-in-Chief for more than two years. Her work has also appeared in Forbes, and she previously served as the Country Music Expert for Answers.com. Widely recognized for her expertise, Black has appeared as a featured guest on The Bobby Bones Show, BobbyCast, and Scripps News Morning Rush, providing insight on country music’s biggest moments. She has also hosted Country Now Live, a concert series featuring performances from artists including Lady A, Dierks Bentley, Riley Green, Jordan Davis, Dustin Lynch, Gabby Barrett, Brett Young, Jon Pardi, Kip Moore, Chris Young, and more. The series has welcomed thousands of fans in person while reaching millions more online. In addition, she hosted Connect With Country Now, a weekly interview series featuring conversations with rising country stars. Throughout her career, Black has earned a reputation for discovering and championing artists long before they become household names. She has covered Luke Bryan since the early days of his career, beginning when he was writing songs for other artists, including Billy Currington’s No. 1 hit “Good Directions,” before stepping into the spotlight with his debut single, “All My Friends Say” and eventually becoming one of biggest names in music. She also gave Megan Moroney her first opportunity to walk a major red carpet as Country Now’s official guest correspondent at the 2022 CMA Awards. An interview she conducted in 2018 for Forbes.com with Luke Combs that inspired his multi-week No. 1 hit, “Doin’ This.” She has also hosted stages at CMA Fest, moderated an industry panel at Country Radio Seminar, and helped lead important conversations about the evolving landscape of country music media. Beyond journalism, Black has also used her platform to support charitable causes and highlight organizations making an impact. Through Country Now Live, she has helped raise awareness and support for St. Jude Children’s Research Hospital, while also advocating for animal rescue through Country Now’s Pupdate series, spotlighting organizations including MuttNation Foundation, Wags & Walks, and Proverbs 12:10 Animal Rescue. Black has been recognized as one of Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. She is a longtime member of both the Country Music Association (CMA) and the Academy of Country Music (ACM). After nearly 20 years covering country music, Lauren Jo Black has spent her career telling the stories behind the artists, songs, and moments that have shaped the genre. Her first-ever book, Country Music Forever: An A-to-Z Celebration of Icons, Songs and Stories, brings that same passion and firsthand knowledge to the page, celebrating not only the legendary artists and timeless songs that have become the soundtrack to generations of fans, but also the places, traditions, and cultural moments that have made country music one of the most beloved genres around the world.