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 Yes, and as I said, it is a cruel irony that the political success of his party requires the failure of his policies - regardless of whether or not he wants them to succeed.
Your "irony" has no consequences whatsoever, because it could apply to almost any situation. By the same logic, it is beneficial for any politician who rallies around any policy to fail in his or her endeavors. For example, I could argue that it is beneficial for the Republicans to never pass an amendment criminalizing abortion, or an amendment banning gay marriage.

In fact, I'd go as far as to say that your point is incredibly disingenuous. By saying "Democrats are better off as long as they fail at their policies," you're really implying "Democrats intentionally fail at their policies."

 Is it better? The Democratic party exists by convincing people they are incapable of supporting themselves.
This is pure opinion.

 They are. See, that's the point you and the Democratic party as a whole are missing - even though you've seen the data. The Republican party has had a stranglehold on national politics for 25 years because people believe in the American Dream and with them in power, the American Dream has been happening for more and more people. They believe that if I try hard enough, I can succeed and I don't need a government handout to do it. And you know what? They are right. Naked capitalism is what drives the US's economy and is the reason why odds are you'll have a bigger house than your parents did.
First of all, do you really believe that the Republicans are for naked capitalism? They may not be for social welfare, but they're all about the corporate welfare. Just go back and look at the Republican Congress' voting record. For God's sake, they extended the copyright term by 20 years solely for the benefit of Disney, one of the world's largest corporations. Most Republicans are also for putting caps on medical malpractice judgments, even though the experts have determined that malpractice insurance accounts for less than 1% of the total health care costs (yes, that includes "defensive medicine"). Tell that to the widow of a man who died in routine surgery because his multimillionaire surgeon had a few too many at lunch.

Secondly, the American Dream® is simply not possible for everyone. It's easy for you or me to think so, growing up at least somewhat intelligent, but tell that to the poor kid with an IQ of 80, or to the single mother who works two jobs just to feed her kids. I guarantee you that you do not work as hard as millions of people who are significantly worse off than you (though it is very easy for someone to delude themselves into thinking otherwise).

 And yet, people vote for them. Why? Unless the Democratic party accepts the reality that people are interested in fairness and the American Dream (and naked capitalism is the primary component of both), they will never understand why a party who (in their minds) only cares about 5% can get 55% of the vote. They're not even trying to understand(or, perhaps, simply cannot accept) where those other 50% come from. And if they won't - they have no hope of ever convincing that 50% of the population to vote for them.
They get 55% of the vote for three reasons. First, they're funded better, mainly because they're typically richer to begin with. Believe it or not, statistics have shown that the more money you spend on a campaign, the better you do. Now, I guess you could make the argument that the richer you are, the smarter and therefore more qualified you are to have the job, but I don't think you want to go down that road.

Secondly, they've shown themselves to be better at universally using easily-digestable labels (e.g., flip-flopper, liberal, East Coast Liberal, West Coast Liberal, tax-and-spender, womanizer, soft on defense, soft on crime, cut-and-runner, etc.) I'm not saying that these labels mean anything; rather, they're just fodder for the more easily brainwashed among us.

Finally, Republicans are better at getting out the vote from the Religious Right by playing up such "issues" as gay marriage near election time. Is it a coincidence that the last time I heard the words "gay marriage" in the press was in November 2004? (Speaking of the religious right, the Republican party has completely controlled the government for almost two years now. If they really care about abortion so much, why haven't they even attempted to pass a Constitutional amendment banning it?)

Actually, in retrospect, I forgot about two other sources of votes for the Republican party. One is from people whose parents were staunch Republicans, and would never change their beliefs no matter what evidence was presented, because they have been ingrained from birth. (To be fair, Dems also have these votes.) The other is from people who were or are in the military. The Republicans have shown a willingness to fund them far beyond what is necessary, and have even made baseless wars to keep them employed.

 Again, what you and your party just plain don't/refuse to see is that the Republican simply have a different (and, as history and economics show, better) way of dealing with the problem of poverty.
This assertion is completely baseless. Sure, the Republicans may have controlled the government during a period of economic growth, but so have the Democrats. I would like to see some statistics backing up your argument that their way of dealing with poverty is "better." From what I've heard, the number of people in this country under the poverty line has increased by 4 million people in the last six years.

 Democratic policies toward the rich are putative to the point they can be considered nothing else.
Do you know how our tax system is supposed to work? Across the board, everyone is (in theory) supposed to pay the same percentage of their income as taxes. While income tax may favor the poor in lieu of the rich, other taxes, such as sales tax, greatly favor the rich. (Someone making $20,000 a year is going to spend a much greater fraction of their income on consumables, and pay more sales tax, than someone making$200,000 a year.) Moreover, richer people typically get the benefit of the corporate subsidies. This is how the system's supposed to work in theory. If you decide to go and give major tax cuts to the rich, assuming that the correct balance had been established before, you've effectively placed a greater burden on the poor. You're mischaracterizing the balancing act as a punishment, which shows a misunderstanding of basic economics.