Heroes come in all forms, makes, models, and in this case, pitching velocities. Tim Wakefield was a knuckleballing Steel City phenom-turned-bust who came to Boston as a last resort and became top three all-time for the Red Sox in wins, games, strikeouts, innings pitched and starts.
He became a Boston icon, seamlessly transitioning from a 19-year playing career to a stellar position as a Red Sox analyst on NESN. Throughout his journey, Wakefield was involved in numerous charities and community outreach endeavors. Sadly, this journey ended on October 1, 2023, when Wakefield passed away at age 57 after a battle with brain cancer.
Wakefield’s career as a major league pitcher was a series of ups and downs. A converted first baseman, he burst onto the scene with an 8-1 record down the stretch becoming a postseason hero for the 1992 Pittsburgh Pirates. When things soured in Pittsburgh, he joined the Red Sox in 1995 and went 16-8.
Wakefield would remain in Boston for 17 seasons as a starter, reliever, and closer, the longest-tenured pitcher in team history. He won more games as a Red Sox than anyone not named Cy Young or Roger Clemens, but still had to fight for a spot on the club each spring.
Wakefield surrendered a home run to the Yankees’ Aaron Boone that lost the 2003 A.L. pennant but was a leader on the 2004 team’s surge to an historic championship. He had ERA’s as low as 2.81 and as high as 5.48. He had double digit wins 11 times and single digit wins 6 times. His career truly was a profile in determination.
I spoke to Wakefield in a 2016 interview and he talked about his career. “I never in my wildest dreams envisioned that I would be the longest tenured pitcher in the history of the Boston Red Sox. I was called up in August of 1992 with Pittsburgh and really was running on the fear of failure.
“I didn’t have any mentors at the time. I enjoyed playing for (Pirates’ manager) Jim Leyland, but he really didn’t like rookies or pitchers. People thought it was lightning in a bottle or that I was just a flash in the pan.”
Wakefield’s post-1992 career in Pittsburgh upheld that notion. Having worn out his welcome with the Pirates, Wakefield was brought to Boston by then-Red Sox GM Dan Duquette. Team scout Eddie Haas suggested that he work with knuckleball legends Phil and Joe Niekro.
It worked. In Boston, Wakefield was effective as a starter, middle reliever, setup man, and closer, but even with the wins piling up, he never felt a sense of career serenity. “I was pretty much in survival mode in Boston from day one,” he related.
“I was always scared to lose my job and I just grinded it out for 17 years. Even after six or seven years with the team, I never felt confident with the Red Sox. I could never relax.”
The high point of Wakefield’s career was that 2004 title. He told me, “In 2004, I really saw the concept of Red Sox Nation come to fruition. Winning the championship was most special because of the generations and generations of Red Sox fans, people going to the cemetery after we won it. It was all pretty amazing.”
Wakefield would win another title in 2007 and retired after the 2011 season. While a career in television was not on his planned retirement agenda, he jumped at the opportunity when it presented itself.
“(Red Sox owner) Tom Werner asked if I’d be interested in joining NESN,” Wakefield explained. “I didn’t want to get into anything full-time, so I did five or six games to see if I liked it. It’s a great way to stay in the game.”
As an analyst, Wakefield was adept at pinpointing pitchers’ issues with mechanics, location, and confidence. He could also analyze hitters, fielders, and specialists due to his years in the game. His style was laid back and calm, and his analysis was always on point and enlightening.
In the aftermath of his passing, several media personalities expressed their sadness on social media. NESN’s Tom Caron stated, “Worked with him for 12 years. Covered his career for 17 years. Don’t think I’ll ever meet someone who meant so much to Red Sox Nation and did so much for so many.”
Former teammate and current MLB Network personality Kevin Millar posted words of friendship, memories, competition, and family stating, “I will miss you and never forget you. I thank you, and may you rest in peace my friend.”
NBC’s Kathryn Tappen, a former NESN reporter, added, “Tim was pure goodness. I will cherish the memories we shared over the years. Heartbroken for all who knew him. Heaven gained a special angel. We love you, Tim.”
As a pitcher, broadcaster, and philanthropist, Wakefield always remained true to his reputation as one of the really good guys in sports, a trait I experienced first-hand for that 2016 interview.
I was writing a column for a Boston baseball magazine and wanted to interview Wakefield for a story. I worked through the media relations staff at NESN to secure a telephone interview with him.
At the time of the interview, he was driving to an event, so we had about a half hour to chat. We talked about that phenomenal start in Pittsburgh, some down years, his arrival in Boston, and his yearly challenge to be part of the Red Sox rotation.
In the course of our conversation, it became clear that Wakefield was also a tremendous golfer. In fact, he had played such hallowed golf grounds as St. Andrews, Kingsbarns, Castle Stuart, Royal Dornoch, and Augusta.
As he neared his destination, and what was supposed to be the end of our interview, I asked him if we could maybe chat another time so that I could also feature him in my column for a regional golf magazine.
Instead of giving me the brush off or telling me to give NESN a call back, he parked his car at his event and said he could talk with me as long as I needed to get the second interview done.
It was a grand gesture from a man who had something to do that was obviously more important than an interview with a writer whom he had never met. We ended up talking for another 20 minutes about his golf game, favorite courses, and his passion for both sports.
When I asked Wakefield about his 2004 Red Sox World Series experience, he was predictably unselfish, saying, “I thought about ex-Red Sox players who never had the chance to win a championship like Johnny Pesky, Luis Tiant, Carl Yastrzemski, and Dwight Evans.”
Tim Wakefield was smart, engaging, interesting, and as friendly a media personality as I have ever interviewed. He was not only a terrific pitcher and commentator, but a giving man whose grace, perseverance, and impact will be sorely missed.
John Molori is a weekly columnist for Barrett Sports Media. He has previously contributed to ESPNW, Patriots Football Weekly, Golf Content Network, Methuen Life Magazine, and wrote a syndicated Media Blitz column in the New England region, which was published by numerous outlets including The Boston Metro, Providence Journal, Lowell Sun, and the Eagle-Tribune. His career also includes fourteen years in television as a News and Sports Reporter, Host, Producer working for Continental Cablevision, MediaOne, and AT&T. He can be reached on Twitter @MoloriMedia.
