Stephen A. Smith explains that the Red Sox's initiative to distance themselves from former owner Tom Yawkey could change others' negative perception of Boston. (1:35)

Boston Red Sox owner John Henry has wanted the city to change the name of Yawkey Way for a while, and the current political climate might provide the right timing.

Henry told the Boston Herald that he is "haunted" by the racist legacy of previous owner Tom Yawkey, who led the team from 1933 to 1976. Although Yawkey is in the Baseball Hall of Fame, he also owned the last team in Major League Baseball to integrate -- 12 years after Jackie Robinson broke the color barrier. Even after integrating, Boston was known as an uncomfortable place for players of color to play.

Yawkey Way is a gathering spot for fans before and after Red Sox games. AP Photo/Michael Dwyer

Henry wants to put that past behind the team, without diminishing the good work that the Yawkey Trust has done. Funded in large part by the $700 million sale of the team to Henry, the trust has helped many worthy causes over the years.

"I discussed this a number of times with the previous mayoral administration and they did not want to open what they saw as a can of worms," Henry told the Herald in an email. "There are a number of buildings and institutions that bear the same name. The sale of the Red Sox by John Harrington helped to fund a number of very good works in the city done by the Yawkey Foundation (we had no control over where any monies were spent). The Yawkey Foundation has done a lot of great things over the years that have nothing to do with our history."

On Thursday, a spokesperson for current Boston Mayor Marty Walsh told the Boston Herald that the mayor is supportive of renaming Yawkey Way.

Henry said he'd like to rename the street that runs alongside the ballpark "David Ortiz Way" or "Big Papi Way," after the retired Red Sox slugger, but Henry doesn't run the process.

"The Red Sox don't control the naming or renaming of streets," Henry said to the Herald. "But 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 multi-cultural, but stand for as many of the right things in our community as we can -- particularly in our African-American community and in the Dominican community that has embraced us so fully.

"The Red Sox Foundation and other organizations the Sox created such as Home Base have accomplished a lot over the last 15 years, but I am still haunted by what went on here a long time before we arrived."

As other teams abandoned the color barrier, the Red Sox held out, giving Robinson a tryout and scouting Willie Mays but opting to sign neither. The club eventually signed Pumpsie Green as its first black player in 1959 -- more than a decade after Robinson debuted for the Brooklyn Dodgers and even after Willie O'Ree took the ice for the Boston Bruins as the first black player in the NHL.

"When we got here in 2002, one of the first things (Henry) did was acknowledge the shameful past in terms of race relations and inclusion,'' Red Sox president Sam Kennedy told The Associated Press.

Still, the team has struggled to accomplish its goal of making Fenway more welcoming to minorities.

In May, Orioles outfielder Adam Jones said a fan called him a racist slur; Kennedy apologized. The same week, a fan was banned from the ballpark for life for using a variant of the N-word while speaking to another fan about the national anthem singer.

The Red Sox also distanced themselves from their flagship radio broadcaster, WEEI, when hosts doubted Jones' version of the events; former Red Sox pitcher Curt Schilling also said Jones was lying.

The country, meanwhile, also is currently reassessing symbols that evoke racism. The Charlottesville, Virginia, riots and subsequent death of a woman protesting white supremacists were fueled in part by calls to take down a statue of Confederate Gen. Robert E. Lee.

Hall of Fame NFL coach Tony Dungy is spearheading an initiative to move a Confederate statue from in front of a courthouse in Tampa, Florida, and he has received the support of the local professional teams, the Rays, Buccaneers and Lightning.