The best interpretation of Tom Yawkey's history of race with the Red Sox is "unfortunate." The team was the last to integrate, they passed on numerous African America megastars, and he let well-known bigot Joe Cronin run the organization during integration, and Cronin's bigotry was a factor in how he evaluated players.
So even if we somehow knew Tom Yawkey personally wasn't racist, as the owner he failed the organization and it will forever be a stain on the Red Sox as a result. It doesn't matter if it was because of economics or animosity or whatever, the Sox ****ed up under his watch. It reflects poorly on the team and the city.
That's why for some fans seeing him honored by both the team and the city with a street named after him isn't about him, it's a constant reminder of an indefensible time period in this city's history. I don't break down in tears or get angry, but it bothers me and has for awhile now. I didn't use to care at all, but the older I get and the more I hear from other people with dramatically different life experiences, the more I understand why that name carries so much baggage, and why that street being named for him can feel so unwelcoming.
If anything changing the street name isn't just about taking away an honor from him, it's a way to let some people stop only thinking about this one issue when they think of him. "Yawkey" at Fenway comes with a very unfortunate, indefensible race policy that did real damage, to real people and to the team's standing. "Yawkey" at a hospital is about saving lives. I would bet more people think about him negatively when they see "Yawkey Way" than they would normally.
It's a small thing, but it will carry a lot of meaning for fans who feel like the Red Sox have never stopped ignoring an ugly time in the team's history.
Tom Yawkey and his memory isn't going anywhere any time soon. But it will be nice not to think about him when I walk into Fenway.