Neither of these policies are particularly popular, and this presents a significant obstacle to Mr. Obama's re-election. Polls have consistently shown lukewarm support at best for the stimulus package, with a clear minority of Americans believing that Mr. Obama's policies have actually helped the job situation.
Similarly, Americans have consistently favoured the repeal of Obamacare by a significant majority. The individual mandate in particular is dangerously unpopular from a political perspective:
Americans overwhelmingly believe the "individual mandate", as it is often called, is unconstitutional, by a margin of 72% to 20%.
Even a majority of Democrats, and a majority of those who think the healthcare law is a good thing, believe that provision is unconstitutional.
The Supreme Court this week heard oral arguments over the constitutionality of the health care law, with a decision to be handed down by the nine justices prior to the presidential election in November.
Day two of arguments was concerned solely with the individual mandate, and by all accounts proceedings went horribly wrong for the law's defenders. Solicitor General Donald Verrilli was peppered with questions by the justices, and he often lacked satisfactory answers.
Importantly, Justice Anthony Kennedy, the so called 'swing voter' of the court, seemed to be disposed against the government's arguments.
It is almost certain that Justices Ruth Bader Ginsberg, Stephen G. Breyer, Sonia Sotomayor and Elena Kagan will rule that the mandate is constitutional.
Meanwhile, Justices Samuel Alito, Clarence Thomas, Antonin Scalia and John Roberts are equally likely to side with the challengers. This leaves Justice Kennedy with the deciding vote.
Thus there does seem to be a tangible risk that the individual mandate, if not the entire law, will be deemed unconstitutional by the Supreme Court. What would this mean for the President and his chances of re-election?
Wall Street Journal columnist Peggy Noonan captures what the sentiments of the American people would likely be, given a hostile decision by the court:
The constitutional law professor from the University of Chicago didn't notice the centrepiece of his agenda was not constitutional? How did that happen?
Maybe a stinging decision is coming, maybe not, but in a purely political sense this is how it looks: We were in crisis in 2009 - we still are - and instead of doing something strong and pertinent about our economic woes, the president wasted history's time.
With Americans largely believing that his stimulus package was ineffective, President Obama needs his healthcare law to be upheld, even if it remains unpopular. Otherwise he will be left broken, embarrassed, and without any record of significance after a full term in office.