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Story highlights

Rachel Sklar: It seems obvious that Donald Trump must envy Hillary Clinton, who won popular vote but doesn't have to do the job

Now Trump actually has to govern, something he never bargained for, she says

Editor’s Note: Rachel Sklar is a New York-based writer and co-founder of Change the Ratio, which aims to increase visibility and opportunity for women in tech and new media, and TheLi.st, a network and media platform for women. She was a volunteer for Hillary Clinton’s presidential campaign. The views expressed are her own.

(CNN) —  

Even the most diehard Democrat has to admit that Donald Trump has it pretty good.

He’s rich. He’s powerful. He was just elected President of the United States of America.

Sure, he’s no longer as young as he once was when he boasted about grabbing women by the – what was that word? – or stiffing undocumented Polish workers or publishing full-length newspaper ads calling for the return of the death penalty in New York, stirring fear by invoking a crime of which 5 black teenagers were later exonerated by DNA evidence. He doesn’t have the cheekbones of Milo Ventimiglia or the sex appeal of Idris Elba or the fingers of Michael Fassbender.

Rachel Sklar
Rachel Sklar

But he was just elected President, and, much as it pains me still to type these words, leader of the free world.

And yet I can’t help thinking that Trump is incredibly jealous of one person right now: Hillary Clinton.

She may not have cracked that highest, hardest glass ceiling, but she did crack his dream outcome: not being president. Even more, she managed not to be president while winning not just the popular vote but winning it by a huge margin.

That’s the kind of loser Trump would name a “winner” – if it had been him. And oh, how he seems to wish it had been. What else can you call someone with 306 Electoral College votes to date who still tweets baseless claims about “millions of people who voted illegally” costing him the popular vote? Sore winner much?

Sure, Trump loved winning the presidency. Who wouldn’t? But he really doesn’t seem to like doing any of the stuff that goes along with it – living in the White House (not enough gold), receiving intelligence briefings (not enough Ivanka), divesting his business assets (Now? When he can finally get rid of those wind farms? No way.)

It seems clear that Trump never really contemplated what it would actually mean to take the office of president. (Political journalists reported that closest allies weren’t sure he wanted it, and during the campaign there was even speculation that he’d quit if he won, which Trump himself did not deny.)

But winning the popular vote? By a landslide? Under that scenario, Trump would have the freedom to brandish a win without changing anything about his life – and even better, he would have a reason to play the victim, emerging as the hero railing against a rigged system (the one role he’d actually prepared to take on). Instead of pretending to enjoy spending quality time with Reince Priebus, he could call in to morning shows and subtweet Hillary Clinton, enjoying all the media coverage without being accused of destabilizing world markets or tearing at the very fabric of democracy.

Here’s how we can tell he’d rather be doing that – because he is doing it anyway. Trump is so unnerved by Clinton’s popular vote win that, like Kristen Wiig’s one-upping character Penelope on “Saturday Night Live,” he’s claiming that his popular vote win would have been even more popular. He’s so annoyed by the drive for recounts in Wisconsin, Pennsylvania and Michigan that he’s proclaiming his vote rigged, too (even though he, you know, won). He doesn’t need no stinkin’ computer scientists and their statistical models and sub-1% margins, and he definitely doesn’t need no stinkin’ Russian hackers. He’s a victim too. And also the “Hamilton” cast members are a bunch of mean old bullies!

But as Trump is learning, it’s different doing all of this as President-elect. Even though it may distract momentarily from his multi-emolument nest-feathering, he is still under scrutiny for things he thinks are perfectly reasonable, such as passing the running of his business on to his adult children and then having them visibly meet with world leaders or alleging unsubstantiated massive-scale voter fraud. And now he has to manage Kellyanne Conway and Rudy Giuliani who are sending him not-at-all-coded messages through the media, since they know that’s where he’s most likely to look.

Meanwhile, Clinton is taking hikes, going to bookstores, receiving public love notes and taking more hikes. With the exception of hiking and going to bookstores, I bet Trump would think that sounds pretty good.

Of course, there’s no real argument to be made yet that Trump has changed any aspect of his life, or plans to, really. He told The New York Times that conflicts of interest won’t apply to him as President – a reading of the Constitution so generous as to be completely wrong, but that does not seem to trouble him.

And of course, as President-elect he is working within a framework for the next few weeks, which dovetails with the things he likes – creating reality drama with his Cabinet picks (aka finalists!), planning for a big party in his honor (inauguration), announcing a theatrical first day in office and then imagining the fun headlines of his first 100 days in office when he’ll get to do the fun stuff such as nominate a Supreme Court justice.

But that is the easy stuff, that you can plan for. Decisions are tough – if you care enough to think about them, and weigh them, and truly consider them. If, however, they are inconveniences to your cable news diet and grip-and-grins with Indian business associates, then you’re going to delegate, punt or wing it.

The other stuff won’t be so easy, or so fun. It’s the stuff that necessitates security briefings, competent and experienced Cabinet picks and a solid bench of experienced public servants who are the key to the day-to-day functioning of the government. It’s the stuff of being president and commander in chief. It’s the stuff that Hillary Clinton has been doodling in the margins of her briefing books probably since 2008, if not the ‘90s. But this is the Trump administration, and these are decisions – so many decisions! – and they all fall to him.

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Donald Trump – entitled inheritor of so much for so long – is now inheriting the burden of performance, and urgency and expectation. Very soon, he’s going to have to start doing things – or else the American people will turn his biggest weapon against him in four years and say: You’re fired.

And in the meantime, Clinton gets to watch, assess, cock an eyebrow and all too probably find him wanting. And at some point, she’ll let him know it.

She has a Twitter account, too. And a mandate. She did, after all, win the popular vote.