If Sasse wanted to send a message about “pen and phone” governance, he had a fine opportunity to do so last year when the president declared a national emergency at the border and ordered Pentagon funding redirected towards construction of the wall. The House passed a resolution to undo that emergency declaration. It got 59 votes in the Senate. Sasse wasn’t one of them. He whiffed.

The cynical read on that at the time, i.e. my own read, was that he was worried about a primary challenge in Nebraska. He didn’t support Trump in 2016 and had criticized the president from time to time, which made him a potential Jeff-Flake-type target for Trump’s wrath. The criticism noticeably tailed off as Sasse’s primary approached. In the end, he was enough of a good soldier for Trump that Trump ended up endorsing him for reelection. Sasse won his primary by a landslide.

And now, lo and behold, it’s safe for him to criticize the president again. And not just on this. On lots of things. I wonder if Trump wishes he could have that endorsement back.

His new executive orders are bad governance and undemocratic, but are they unconstitutional? Hold that thought.

Sasse: “The pen-and-phone theory of executive lawmaking is unconstitutional slop. President Obama did not have the power to unilaterally rewrite immigration law with DACA, and President Trump does not have the power to unilaterally rewrite the payroll tax law.” pic.twitter.com/bcI0Qiia3d

— Zeke Miller (@ZekeJMiller) August 9, 2020

If Trump really were ordering the continuation of federal unemployment benefits and waiving the payroll tax, that would be unconstitutional. Congress has the power of the purse. But look closer at his new executive orders, says law prof Daniel Hemel, and you’ll find that they’re less bold than that. They may be constitutional in part because they don’t do a whole lot.

The issue is that deferral doesn't ultimately relieve employers of payroll tax liability, so many employers will continue to withhold Social Security taxes from paychecks lest they be on the hook for the $$$ next year. So this likely won't do all that much … 7/

— Daniel Hemel (@DanielJHemel) August 9, 2020

The EO on eviction relief (https://t.co/1y0U3aN3Z4 — this one is actually an EO, not a memo) does absolutely nothing, other than instruct HHS, CDC, Treasury, HUD & the FHFA to maybe do something if they choose 9/ pic.twitter.com/vZ8ywsztc6

— Daniel Hemel (@DanielJHemel) August 9, 2020

The executive order extending unemployment benefits is potentially more meaningful but it requires states to kick in 25 percent of the costs and involves a convoluted procedure in which they’ll essentially have to set up a new program to draw off FEMA funds, a process that could take months even if it’s not bogged down in court challenges.

So, “slop”? Sure. “Unconstitutional slop”? Less sure.

I think the EOs are mostly symbolic. I said on Friday that they’re good politics inasmuch as they show the president attempting to do something to relieve the financial burden on Americans who can’t work because of COVID while Congress, as usual, does nothing. I stand by that, but the politics of his payroll tax EO deserves a little more attention. Trump has been pushing the idea of easing the payroll tax for months as an economic but neither Democrats nor Republicans support it. Democrats don’t like the idea because easing the payroll tax primarily benefits higher earners — and doesn’t benefit anyone who’s laid off right now. Republicans don’t like it because it tees up Democrats to make this argument, which could get hairy for the party in November:

Unable to deliver for the American people in a time of crisis, Donald Trump offered a series of half-baked measures today. He is putting Social Security at grave risk at a time when seniors are suffering the overwhelming impact of a pandemic he has failed to get under control. And make no mistake: Donald Trump said today that if he is re-elected, he will defund Social Security…

Trump announced a payroll tax plan with no protections or guarantees — like the ones the Obama-Biden administration enforced a decade ago — that the Social Security Trust Fund will be made whole. And, Trump specifically stated today that if re-elected, he plans to undermine the entire financial footing of Social Security. He is laying out his roadmap to cutting Social Security. Our seniors and millions of Americans with disabilities are under enough stress without Trump putting their hard-earned Social Security benefits in doubt.

That passage comes from a statement put out last night by Joe Biden, seizing a gift-wrapped opportunity to spook senior citizens about what a second Trump term might mean for them. Some polls earlier this summer showed Biden leading comfortably among those aged 65 or older, an ominous departure from electoral tradition for the GOP. Trump has been more competitive among that group lately but the idea of cutting Social Security’s fiscal lifeline could scare them back towards Biden. Even stranger, Trump said yesterday that he’d look to make his payroll-tax relief permanent if he’s reelected. It’s one thing to say we need to “borrow” from entitlements short-term to help laid-off Americans get through a crisis, but the idea of cutting funding permanently is potentially a serious electoral liability.

Even weirder, it’s unclear if taxpayers will actually see any money from Trump’s payroll-tax measure in their paychecks. He doesn’t have constitutional power to waive the tax, merely to defer collection of it, which means employers and their workers are now facing months of uncertainty about whether the tax will ultimately be owed or not:

The actions will not even provide the payroll tax cut that Mr. Trump has long coveted as a centerpiece of stimulus efforts. They will simply suspend collection of the tax, as one of Mr. Trump’s longtime outside economic advisers, Stephen Moore, has recently urged him to do. Workers will still owe the tax, just not until next year. And while Mr. Moore has said that Mr. Trump could promise to sign a law that would permanently absolve workers of that liability, there is no guarantee that Congress would go along.

The uncertainty raises a host of questions for companies and workers, including a cascade of intricate tax questions, according to a recent analysis published by Joe Bishop-Henchman of the National Taxpayers Union Foundation. (For example: If workers owe less payroll tax, they would owe slightly more income tax; would employers change, on the fly and in the middle of the year, how much income tax they withhold?) He concluded that most companies were unlikely to take any risks.

It feels like a total own-goal. There won’t be any stimulus effect if the deferred taxes continue to be withheld by employers. Even if they aren’t withheld, Trump’s deferral does nothing to help the unemployed and little to help lower-wage workers, who don’t pay much payroll tax. Meanwhile, Democrats will exploit to the hilt the risk posed to Social Security and Medicare by cutting the funding mechanism for those programs. Biden can now even come after Trump at the debates and demand that he explain how he’ll pay for those entitlements if he gets his wish about making the payroll-tax deferral permanent. POTUS will have to choose between saying either that he wants to cut Social Security and Medicare, which would be a disaster, or explaining which other taxes he’d raise and/or programs he’d cut to cover the shortfall to entitlement.

In fact, the entitlement implications of Trump’s payroll-tax order are so juicy for Dems that it’s allowed them to somewhat sidestep their hypocrisy in complaining about Trump using unilateral executive power in a dubious way. Some of them are complaining half-heartedly today anyway, but they know they have no grounds to do so after supporting Obama’s outrageous DACA order. Better to focus on the Social Security implications of Trump’s EO instead. Read Biden’s full statement linked above and you’ll find that he barely mentions the procedural flaws with Trump’s order — and why would he? He wants to be able to exert the same dubious powers if he’s elected, and he understands that Americans’ grasp of civics has decayed to the point that they just don’t much care if Trump has constitutional authority to issue these orders are not. Voters will be much more responsive to scare tactics about slashing Medicare than they will to scary yet true warnings that we’re inching towards dictatorship by continually allowing presidents to act whenever they feel the legislature is moving too slowly.

Here’s a blast from the past via Liam Donovan about how America makes “laws” now.

Still the realest thing SNL has done in the past decade plus pic.twitter.com/jn7VHvsTXg

— Liam Donovan (@LPDonovan) August 8, 2020