Many may be so weary of talk about negotiations on the territorial dispute between Tokyo and Moscow as nothing more than a broken record that they will be tempted to skip this article. To catch their attention, I am starting with three bold statements. First, the talks made considerable progress, especially in 2000-2001 under Putin, and came closer to reaching the point of testing whether a breakthrough was in sight than most realize. There were multiple windows of opportunity during that time, and afterwards, that were closed by diplomatic stumbles, but they should have been left open to see what was possible. Second, the international images of Abe and Putin as driven by national identity extremism and, thus, even more unlikely than other leaders of their countries to reach a pragmatic compromise on a sensitive territorial dispute, misjudge their views on this particular dispute and the signals they have been sending. They are bold leaders, who at this time are in a better position to deal with this dispute than in the past. Third, the geopolitical and domestic contexts in each nation for reaching a deal are decidedly more favorable than ever. These assertions are explained below.