When the Supreme Court begins to deliberate President Barack Obama’s signature health care law Monday, it will serve as a bitter reminder to Democrats of the blows leveled at their causes by the conservative Roberts court.

Though the outcome of the high-profile case reviewing the constitutionality of the health care law’s marquee feature, the individual mandate, is unknown, plenty of other decisions have given Democrats pause or even rallied them to battle with the court in ways rarely seen before.

Perhaps no moment encapsulated the tension between the Democratic agenda and the court’s decisions more than the first nationally televised spat between a sitting president and a sitting Supreme Court justice.

“With all due deference to separation of powers … the Supreme Court reversed a century of law that, I believe, will open the floodgates for special interests, including foreign corporations, to spend without limit in our elections,” Obama said in his 2010 State of the Union address of the controversial Citizens United v. Federal Election Committee’s ruling in front of a joint Congress, a national audience — and most of the Supreme Court.

“Not true,” a stunned Justice Samuel Alito could be seen mouthing to the president on camera.

The tension between Democratic politics and the conservative-leaning court has not been unique to that moment, however. Some of the most criticized cases include Citizens United and a 2007 ruling that rolled back part of the McCain-Feingold campaign finance reform law that barred corporate-funded issue advocacy ads close to an election.

Congress has been happy to engage on other issues — but with mixed results.

There was the floor battle to pass the Lilly Ledbetter Fair Pay Act, the first major initiative signed into law by Obama, in 2009. The legislation, named after the unsuccessful plaintiff in the case, reversed a decision handed down by the Roberts court that limited when women could sue for gender-based pay discrimination in the workplace. Ledbetter had sued Goodyear Tire and Rubber Co. for pay discrimination, but the court said she needed to have filed her complaint within 180 days of Goodyear making the decision to discriminate. Previous precedent held that an employer renewed the discrimination each time it issued a paycheck.

When the bill was introduced in 2008, rank-and-file Democrats took to the floor en masse to malign the court’s decision and reiterate their dedication to reversing it.

“I am pleased that this bipartisan bill seeks to address and correct the Supreme Court’s Ledbetter decision from last spring,” Sen. Jack Reed (D-R.I.) said in an April 2008 floor speech. “As Justice Ginsburg noted in her Ledbetter dissent, such a law is ‘more in tune with the realities of the workplace.’ The Supreme Court majority failed to recognize these realties, including that pay disparities typically occur incrementally and develop slowly over time, and they are not easily identifiable and are often kept hidden by employers.”

After Democrats succeeded in passing the legislation, Obama signed it into law flanked by Democratic leaders and Ledbetter. A year later, to commemorate the anniversary of the law’s passage and facing a tough re-election battle, Senate Majority Leader Harry Reid (Nev.) sat for photographs with Ledbetter in a Capitol suite.

Although the Ledbetter law, approved when Democrats controlled the White House and both chambers of Congress, was their only effective legislative attack on what they consider to be the court’s failings, the party has not stopped trying to construct a campaign narrative around politically unpopular decisions.

Democrats last month refiled the DISCLOSE Act, which failed to pass last year, to address the court’s decision to undo a long-standing precedent that prohibited corporations and unions from spending unlimited funds in political advocacy. The Citizens United case, widely regarded as leading to super PACs, has been deeply unpopular with Democrats, despite the fact that the influx of money could benefit both parties.

Several Democratic aides indicated that while the health care case this week will receive intense coverage, next month’s hearing on a controversial Arizona immigration law might be more important. Arizona’s law requires police to check the immigration status of anyone they suspect of being an illegal immigrant. If the court upholds the law, Democrats could renew their push for immigration reform in a presidential election year when both parties will be vying for the all-important Latino vote.

Democrats have felt somewhat at a disadvantage with the Roberts court and remain wary of the outcome for the law. But Republicans appeared equally nervous about the outcome of the health care case this week.

Senate Minority Leader Mitch McConnell (Ky.) has focused his messaging operation not on the court case but on Congressional efforts to repeal the health care law in 2013, when he hopes his party will reclaim the Senate.

When pressed for further details on what Republicans might do if the court rules in favor for the law, a senior GOP aide said, “Just because Democrats play rapid response with the Supreme Court doesn’t mean Republicans will do the same thing.”