Tony La Russa’s Bet Leads Dave Stewart to Debut Singing Career

Tony La Russa has taken a playful bet with longtime friend and former player Dave Stewart, resulting in Stewart’s first public singing performance scheduled for next Saturday. The event will be part of La Russa’s annual fundraiser at the Lesher Center for the Arts in Walnut Creek, California, benefiting his nonprofit organization focused on animal welfare.

La Russa and Stewart’s friendship began in 1986 when La Russa first managed the Oakland Athletics. He brought Stewart, a right-handed reliever, into the game against Roger Clemens. Stewart not only won that match but went on to secure three World Series championships during his career. Over the years, La Russa discovered Stewart’s hidden talent for singing, a skill he typically showcased only in private settings or after a few drinks.

Stewart, now 68, will perform two songs by Chris Stapleton and one classic by Bill Withers. La Russa fondly recalls how Stewart often sang Motown lyrics at social events, noting, “When he gets excited, he sounds like the Bee Gees.” This performance marks a significant milestone as Stewart has never before shared his vocal abilities on stage with a band.

The inspiration for this unexpected debut came during a golf outing in Phoenix last spring. La Russa, now 81 and a senior advisor for the White Sox, and Stewart made a friendly wager. The consequence for the loser was to sing at the fundraiser. La Russa initially suggested that they could forgo the bet, but Stewart insisted on honoring the agreement.

La Russa humorously added, “I would have had to kiss his (expletive) at home plate before the first pitch” had he lost. This anecdote highlights the camaraderie between the two, showcasing their light-hearted approach to their long-standing friendship.

The fundraiser will also feature notable attendees, including Dusty Baker, Jose Canseco, and Dennis Eckersley, along with musical performances by Tony Lindsay of Santana and Phantom of the Opera singer Franc D’Ambrosio. A panel discussion reflecting on pivotal moments in Stewart’s career will further enrich the event.

La Russa has hosted this fundraiser for many years, often involving Stewart in various capacities. The current gathering is particularly poignant, as it coincides with La Russa’s reflection on his extensive career, which spans over seven decades. He debuted in baseball at just 18 years old with the Kansas City Athletics and returned to manage the Oakland team in 1986, leading them during the iconic “Bash Brothers” era.

As the Athletics prepare to transition to Las Vegas, La Russa expressed disappointment over the team’s departure from Oakland. He noted, “There was all that talk about going to San Jose. I wish that had happened… Now it’s Las Vegas, and I can’t say that we’re not disappointed.”

In addition to his ongoing support for the Athletics, La Russa has faced personal challenges in recent years. He retired midway through the 2022 season due to health issues, including heart problems and cancer treatment. After surgery in January 2023, he began a new chapter as an advisor for the White Sox, a role he embraces as he remains connected to the game he loves.

Looking ahead, La Russa plans to attend spring training in Arizona next February. His passion for baseball remains unwavering, as he continues to engage with the sport and its community. “It’s been my life forever,” La Russa stated, reflecting on his deep-rooted connection to baseball and the friendships he has forged over the years.

As Stewart prepares to take the stage, fans eagerly anticipate this unique performance that intertwines friendship, nostalgia, and a shared love for music and baseball.