By Sahil Kapur

Can Speaker John Boehner defeat President Barack Obama in court?

This month the Ohio Republican plans to secure House approval for a lawsuit alleging that Obama exceeded his constitutional authority by unilaterally delaying the Obamacare employer mandate by one year, to 2015. It’s unclear if the suit has a serious chance of success, legal experts say, but it’s plausible.

The first question is whether Boehner can achieve standing to bring the litigation in the first place. This is uncharted waters for House of Representatives. Never before have the courts granted standing to lawsuit emanating from Congress against a president’s executive actions. There have been previous lawsuits of the sort brought by individual members of Congress, but those have been thrown out for lack of standing.

Some legal experts believe Boehner is destined to lose on the same grounds.

“The House of Representatives as an institution hasn’t suffered the sort of concrete, particularized injury that the courts are constitutionally empowered to review. This is a political dispute, not a judicial dispute, and the courts will properly leave it to the political branches to sort it out,” wrote Nicholas Bagley, a professor at the University of Michigan Law School.

The upside for Boehner is this is also new territory for Obama. Never before has the House voted to authorize a right of action to sue a president. Statutory deadlines are one way for the legislative branch to force executive moves, and it’s not apparent that Obama’s decision to delay enforcing the mandate to Jan. 1, 2015 is the sort of thing that has been tested in court before.

“Courts have never approved this sort of thing, but they haven’t had to address it before,” said Jonathan Adler, a professor at Case Western Reserve University Law School. “So while House action is unprecedented, executive authority asserted by administration is arguably unprecedented too.”

If Boehner cannot win on standing it’s game over for him. The lawsuit is dead.

But if the courts decide the House has a legal right to sue the President, he may have better luck winning on the merits of the case.

Bagley argues that while federal agencies have flexibility on how best to enforce the law, the Obama administration’s public announcement that it would disregard the tax penalty for non-compliant employers, even temporarily, is problematic from a legal standpoint.

“At what point does a decision not to enforce the law ripen into a decision to dispense with it?” he wrote in the New England Journal of Medicine. “Encouraging a large portion of the regulated population to violate a statute in the service of broader policy goals — however salutary those goals may be — probably exceeds the limits of the executive’s enforcement discretion.”

Adler agreed: “I think the case on the merits is very strong,” he said, calling the Obama administration’s rationale for the delay “quite weak.”

There is strong disagreement on that question, though.

“I think this is a transparently baseless allegation of illegal, let alone unconstitutional behavior by the President,” said Simon Lazarus, senior counsel at the Constitutional Accountability Center, a liberal legal advocacy group. “It is the kind of good-faith, common-sense exercise of judgment of how best to implement a complex new law, with myriad ramifications and points of contact with existing laws and programs, that the framers had in mind when they provided that the president was to ‘TAKE CARE to see that the LAWS be FAITHFULLY executed.'”

Lazarus and Walter Dellinger, a former acting solicitor general for the Clinton White House, will be the Democrats’ witnesses in the House Rules Committee hearing next Wednesday on the draft legislation to authorize the lawsuit. The GOP’s witnesses will be Jonathan Turley, a professor at George Washington University Law School and Elizabeth Price Foley, a professor at Florida International University College of Law.

The lawsuit may percolate in the courts for a while — perhaps years, depending on how quickly the courts decide to act.

“The irony is by the time some of this is resolved through the court system he may no longer be president,” Sen. Marco Rubio (R-FL) said this week.

The optics of suing Obama to implement an Obamacare tax are bizarre for Republicans. Boehner chose this particular issue for legal reasons, an aide to the Speaker said, because he believes it would “give the House the best chance of success in the courts.”

The White House called the lawsuit “disappointing” and “a political stunt.” Spokesman Josh Earnest said Thursday that Obama is “doing his job – lawsuit or not – and it’s time Republicans in Congress did theirs.”