Gore did win that election, but SCOTUS illegally decided it instead of a fair ruling requiring Florida to recount ballots using the same methods in all districts. Americans should have done general strikes and rioting.
I don't know about 9/11, but I doubt Gore's SCOTUS appointees would have made the incorrect decision on Citizens United. America would be in a better place today.
The Supreme Court did require Florida recounts of ballots using the same methods in all districts, and remanded the case to Florida Courts to figure out if there was a legal way to extended the deadline for recounts, to get it done, but they never heard the case, because Gore conceded soon after.
I don't know about 9/11, but I doubt Gore's SCOTUS appointees would have made the incorrect decision on Citizens United. America would be in a better place today.