Tony La Russa is a Hall-of-Famer, a four-time manager of the year, a three-time World Series champion and the winningest manager in baseball in the last 75 years.

But when the Chicago White Sox named La Russa their new manager on Thursday, hiring him to guide a young, talented roster that this year earned the franchise its first playoff appearance since 2008, it was as risky a managerial move as any in recent memory.

La Russa is 76, having last managed in 2011, when he guided the St. Louis Cardinals to the World Series title. He retired shortly afterward, ending (or so it appeared) a 33-year managerial career in which he won 2,728 games, the third-most in history behind only Connie Mack and John McGraw. He was elected to the National Baseball Hall of Fame in 2013.

The move appears to be White Sox owner Jerry Reinsdorf’s attempt at correcting what he considers one of the biggest mistakes of his tenure there — firing La Russa as manager in 1986 after seven seasons on the White Sox’s bench. Since then, La Russa went on to win one World Series title with the Oakland A’s and two with the Cardinals, gaining a reputation for being ahead of the curve in strategic deployments such as bullpen specialization.

Since retiring in 2011, he had worked in the front office of MLB, as well as for the Boston Red Sox, Arizona Diamondbacks and most recently the Los Angeles Angels.

“As everyone in baseball is well aware, I have always respected Tony and am proud to have maintained a great friendship with him over the decades in the game,” Reinsdorf said in a statement. “But his hiring is not based on friendship or on what happened years ago, but on the fact that we have the opportunity to have one of the greatest managers in the game’s history in our dugout at a time when we believe our team is poised for great accomplishments.”

The White Sox fired Rick Renteria as manager shortly after this season, which saw the White Sox go 35-25 and finish tied for second in the American League Central. The White Sox lost in three games to the Oakland A’s in the first round of the playoffs. They have been considered a rising power for several years now, and appear poised to build off this year’s success in the coming years.

The White Sox, however, haven’t made back-to-back playoff appearances in their 120-year history.

“We are extremely excited about the future of this team,” general manager Rick Hahn said in a statement. “As we showed in 2020, this is a young, talented club that we expect to only grow better and better in the coming years. Adding in a Hall of Fame manager who is recognized as being one of the best in the history of the game, we are a step closer to our goal of bringing White Sox fans another championship.”

The White Sox are not known to have interviewed other candidates for the job besides La Russa. In hiring him, they may have been swayed at least in part by the success this season of 71-year-old Dusty Baker, who was hired to guide the Houson Astros beyond the sign-stealing scandal of this winter and who took the team to the American League Championship Series before losing to the Tampa Bay Rays.

“While I have had other inquiries about managing since retiring, this opportunity with the White Sox brings together a number of important factors that make this the right time and the right place,” La Russa said in a statement. “The on-field talent is amazing, and the front office … has done everything necessary to create an atmosphere of long-term success. All of those factors aligned to make this a tremendous opportunity, and I am excited to get going as soon as possible by building a coaching staff and getting to work.”

But it isn’t only La Russa age — only Mack and Jack McKeon were older — that makes his hiring a risky move. He has also been outspoken against athletes kneeling during the national anthem, saying in an interview with Sports Illustrated in 2016 that it is “disrespectful” and questioning the “sincerity” of quarterback Colin Kaepernick.

“Even if he was sincere,” La Russa said of Kaepernick, “there are other ways of showing your concern. Disrespecting our flag is not the way to do it.”

One of the White Sox’s team leaders, shortstop Tim Anderson, serves on the board of the Players’ Alliance, a nonprofit made up of current and former Black baseball players that formed out of the swell of protests for social justice this summer following the death of George Floyd. Its mission, according to its website, is “To create an inclusive culture within baseball and the community, where differences are leveraged to elevate racial equality and provide greater opportunities for the Black community.”

Before the White Sox’s Opening Day of 2020, Anderson and teammates Jose Abreu, Eloy Jimenez, Luis Robert and Lucas Giolito — who form the core of the White Sox’s young and talented roster — all knelt during the anthem.

Before La Russa ever sets foot in the White Sox’s dugout, he will need to initiate honest discussions with those players and others about his stance on those matters. Baseball in 2020 is different from it was the last time La Russa managed, and so for that matter is America.

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