1. Truman is viewed as a great President by historians, not simply as an average President. And even if Iraq becomes a permanent democracy and causes a domino effect throughout the Middle East causing the other dictatorships there to collapse as well, Bush would still be regarded as a miserable failure due to the financial crisis.
2. Jeb certainly doesn't have a political future. Maybe George P. or some other younger Bush does, but probably not for 20-30 years. Many young people still remember Bush pretty well and view him as a horrible President, and they are still going to be a large voting bloc for 20-30 more years.
If that happens (bolded) GWB would go down in history as a military and diplomatic genius, although still as a failure on the economic front.