1. For the United States to develop into the nation we are today, was it inevitable that native Americans had to be subjugated, their lands taken away, and their culture destroyed?
Not like we can have a do over, but even if we could I don't see another way to get here.
2. Was it legal and Constitutional for the southern states to secede from the United States in 1860 and 1861?
No. But whether that was settled in 1861 or 1865
3. Was FDR's New Deal good for the United States?
Of course. If nothing else it bought off the threat of an attempt at a communist revolution.
4. Were the atomic bombs dropped on Hiroshima and Nagasaki a justifiable act of war?
Yes, but I don't think they achieved any real WWII objective that wasn't going to happen anyway - no invasion necessary. Cold war objectives on the other hand,
5. Was the Vietnam War winnable for the United States?
Nope.
6. Do you give President Reagan credit for helping to win the Cold War?
Sure. Reagan legitimized the "moral high ground" policies that were ridiculed under the previous administration that resulted in providing the much needed moral support for the growing dissident movements. However, the "offensive" military build up probably delayed the actual end.
7. Did George W. Bush fairly win the Presidential election of 2000?
Gore most likely received the most votes in Florida, but Gore would have lost each and every of the recounts he requested. (I think he only wins under one recount scenario - the "intent of the voter" for the entire state.) So with the results as close as they were and with the various screw ups I think it easy enough to see Gore losing most "fair" recounts anyway. However, neither supreme court did anyone any favors here. So that would seem fair to me,
Now if you asked about 2004 Ohio....
8. Could our government reasonably have prevented the events of September 11, 2001?
Sure, but I don't think the one intelligence briefing would have been enough. And I'm not sure that I would find the means to know enough, do enough to thwart it would be acceptable.
9. Was the invasion of Iraq in 2003 a good decision?
Candidate Bush provided a list of conditions that had to be met to justify placing our military in harms way. The invasion did not even satisfy those requirements. As for the stuff that we knew we would
However, except for needing to staying forever because of the power vacuum created I'm not so sure how this deployment was all that different from the Clinton era usage of the military force. Since that power vacuum had only handcuffed the two previous administration's options for the previous dozen years, how important could it have been?
10. Was the withdrawal of American troops from Iraq in 2009/10 a good decision?
It was the only available decision.
11. Was TARP and the stimulus package necessary for saving our economy?
The economy would have recovered on its own and arguably would be stronger for it. That being said I assume you mean that were they necessary to avoid a great deal more economic pain. Of course.
12. Should the middle class and wealthy pay more in taxes so that poor people have better access to health insurance?
I'm not sure. I'd argue that the working poor, lower middle class
is paying more in taxes today to provide better access to health insurance to seniors and those with good paying jobs and employer provided health care. And as a result are driving costs out of reach for their own health care. This being offset somewhat by the upper middle class and wealthy providing the crappiest health care of them all - Medicaid to the poor. Especially those lazy good for nothing kids.
So is undoing this a Yes?
13. Should the middle class and wealthy pay more in taxes so that poor people have access to welfare and food stamps?
We shouldn't have need based welfare or food stamps. We should send all Americans a monthly check instead. So this would be a yes.
14. Is gay marriage a federal right under the 14th Amendment?
I wouldn't word it that way, but we are well beyond the point of seriously thinking otherwise.
15. Would universal background checks on gun purchases or universal gun registration violate the 2nd Amendment?
No
16. Was Roe vs. Wade good law, in terms of it's interpretation of the Constitution?
As in finding that the constitution provides a "right to privacy"? If so yes. Beyond that it might get messy.
17. Are the employment and legal woes of so many African-Americans in this country, today, due mostly to lingering racism?
If you mean largely due to racism being exercised in 2014 then I'd say no. If you mean by the impact of racism exercised the past 400 years then absolutely.
18. Should the United States continue it's close relationship with the State of Israel?
It is time to make friends with Iran and wipe Israel off the map. Sorry couldn't resist. Israel is a huge pain in the

for us, but ultimately this where our values survive and thrive in that region. So yes,
19. Is the mass collection of private emails and phone records, justified by collective warrants, a violation of the 4th Amendment of the Constitution?
There is no justification for this, but I assume I will always lose to those that are too afraid.
20. Should illegal immigrants already living in this country eventually be given legal status and a means to become citizens?
Of course. We should value those that take such initiative. Why would we want more people willing to queue up and wait in lines?
(I mean other than the fact that it is probably easier to compete with the latter.)