FDR and Obama appointments to the Supreme Court were very far left if not socialists. Hugo Black gained confirmation despite being a member of the Ku Klux Klan (ironically African-Americans began to shift primarily from supporting Republican candidates to Democratic candidates during the FDR years). Frankfurter was confirmed despite a huge upheaval by Jews (The era of Nazi Germany). Republicans gave little fight against leftist Obama appointees – Elena Kagan and Sonia Sotomayor.
Over time, the many socialists in the FDR administration ventured further right. After seeing Stalin as a genocidal tyrant during WWII they felt betrayed by Russia. And after seeing FDR failures in socialism they ventured right. For instance, Rex Tugwell saw his socialism community experiments created in the RA fail and realized that socialism may not be a better option over capitalism. In the Obama administration former loyal servants such as Robert Gibb and Robert Gates have been highly critical of Obama policies.
Probably the biggest personal problem plaguing both Obama and FDR is their indecision. In a time of national security and the economy tinkering on the brink of collapse both men showed a tendency to be uncommitted, flip flopping, and suffering from indecision. FDR openly admitted his opinion on something can change from hour to hour. Obama is so unwilling to make tough decisions he holds far fewer press conferences than any president in the modern era. Obama can give great speeches when reading from a teleprompter, but he does not think very fast on his feet during impromptu situations.
Well, how could such bad Presidents win reelection (FDR – three times and Obama once)? That is an easy question to answer, they bought their votes. The so called liberal forgotten man under Obama is now over 50% of the population. Welfare payrolls have exploded under Obama – Food Stamps, ObamaCare, disability, prolonged unemployment benefits, ObamaCare, housing subsidies and so forth. What’s worse, Obama even removed the work requirement for people to earn welfare. FDR handed out millions of jobs in his social programs, passed unemployment, social security and other handouts. There are other less obvious reasons for their successful reelections such as the Republican candidates were not very strong; massive propaganda programs with people in the arts; and attacks against “bigness”, the wealthy, and corporations – they both were masterful at the art of pitting groups of American citizens against each other. Before the days of FDR, liberalism was defined as the fight for rights for individuals; today liberalism is the fight for rights for groups of people by demonizing other groups of people. For instance, both Obama and FDR expanded the size of the IRS and used them to go after enemy groups. Obama also used the EPA to do this and used the DOJ and NSA to go after conservative journalists. In fact, Obama and FDR spend more time trying to demonize their enemies than trying to end the recession and depression. Keep in mind, much of the Obama and FDR agenda was not always widely accepted. For FDR and Obama it took congressional supermajorities to get their agenda through. And when those supermajorities were no longer there, they used gimmicks like riding their legislation on other bills and using executive orders to get their agenda introduced. It is important to remember that the Democrats had some miserable midterms during the FDR and Obama years not only giving Republicans advantages in Washington, but also on the state level. This proved to be important in the Obama administration because states continually fought his bad and failing legislation.