Proceeds from the sale have financed much of the Yawkey Foundation’s philanthropy, but Yawkey’s role in resisting integration has attracted renewed scrutiny recently in a city where a quarter of residents are black, and the long-held perception has been that it is an unwelcoming place for minorities generally — the comedian Michael Che referred to Boston earlier this year as “the most racist city I’ve ever been to” — and for black athletes specifically.

The Red Sox were the last major league team to integrate, when they promoted infielder Pumpsie Green in 1959, a dozen years after Jackie Robinson broke baseball’s color barrier with the Brooklyn Dodgers. Yawkey had owned the team for more than two decades by then, and he would continue to control it for 17 more.

African-American ballplayers have spoken for years about the difficulty of playing in Boston. Just last winter, the Red Sox pitcher David Price — the team’s highest-paid player — told The Boston Globe that racial taunts were directed at him while he warmed up in the Fenway bullpen last season. And this season, Adam Jones, the center fielder for the Baltimore Orioles, said that a fan in the Fenway bleachers had yelled racial epithets at him.

City officials and Red Sox leaders apologized profusely to Jones, and he received a standing ovation from the Fenway crowd when he came to bat the next day. But the episode fed a narrative that the city and its fans — sensitive to the stain it carries — have long tried to change.

“For me, personally, the street name has always been a consistent reminder that it is our job to ensure the Red Sox are not just multicultural, but stand for as many of the right things in our community as we can,” Henry wrote Thursday in an email to the Herald. While the makeup of the team’s roster changed long ago, Henry said he was “haunted” by the team’s complicated racial past.

Yet Henry’s mere suggestion that the team would press for the renaming of the street made the Red Sox the latest organization or figure in sports to enter the kind of polarizing political discussion that athletes and teams have long avoided.

LeBron James and Martina Navratilova, among others, have used Twitter to strongly criticize Trump’s shifting comments about the protests in Charlottesville, and another N.B.A. star, Kevin Durant, said he would skip a possible visit by the league champion Golden State Warriors to the White House because “I don’t respect who’s in office right now.”