Bring in the Boss

In an unwittingly communal effort to highlight the surging popularity of socialism, Warren and Biden and Pete and everyone except Bernie already declared they were not socialists. So how, then, can we be sure that this is a Mike 2020 hat? How does he stand out in a field crowded with centrists and center-leftists? Well, just like with a North Face down jacket—which, incidentally, would also go great with this cap—the branding is on the back. Weirdly, you would only get the message after the hat wearer had passed you by on the street. Is the hat meant to evoke l’esprit de l’escalier?

You keep the boss in the back of your mind at all times, don’t you?

A couple of years ago, in a failed attempt to release decades of frustration with the Democratic Party’s painful, self-defeating rightward drift, I decided to retaliate—via hat. I went on the first embroidery site I could find and made a quick mockup. Text: Make Democrats Great Again; color: purple. The point of the color and the MAGA callback was anticipatory: obviously the Dems would come up with some bullshit imitation of Republican rhetoric—and, worse, policy—and try to “capture the middle” by running on that. The forty-three likes on the image suggest that some of my social media friends found it amusing, and I confess that I still get a chuckle out of it. But I also know that it failed as satire—on two major counts. First, I looked on in sadness as some people reacted to the hat as if it was something the DLC crowd would in fact come up with. Second, my violet MAGA variation was no match for Love Trumps Hate, the immaculate self-own that Hillary Clinton actually ran on. Trump is often said to have moved beyond parody, but in this category, the Democrats would also have a shot at winning the popular vote.

Enter Mayor Bloomberg! A sexist and racist centrist, the former Republican multibillionaire is the walking, talking, smirking embodiment of Make Democrats Great Again. He is richer than Trump; he is more condescending than Trump; and his horrific stop-and-frisk policies have actually been declared unconstitutional, while many of Trump’s own legal efforts are still wending their way through the courts. What’s more, he comes with his own eponymous media outlet. Take that, Fox News! Who needs a middleman? Still, some people are fixated so desperately on conquering the swinging center of suburban America that they have a hard time understanding why exactly Bloomberg is such a bad idea.1

Fortunately, the savvy businessman is selling a hat that does a really good job of explaining this. The front reads NOT A SOCIALIST, in a no-nonsense font (Tabloid Press, unbelievably) that will go great with a crisp white shirt, a nickel gray Patagonia Synchilla vest, and J. Crew 770 straight-fit chinos.2 The cap itself isn’t purple, presumably because in the course of their research (or when watching his first debate appearance), Bloomberg’s army of well-compensated branding experts discovered his aversion to “horse-faced lesbians.” Probably best not to overlap with their signature hue. Or, maybe it was the fact that, as the artist Noah Davis put it, “Purple is to black people what Yves Klein’s blue is to white people”—in which case you could also see Mayor Mike taking a pass. In any event, navy blue is a safe choice, and this hat is about making safe choices. Unless you are Muslim, uninsured, a woman, indebted, Trans, interested in the future of democracy, Black, brown—then the blue here is about something else entirely. It’s about “Vote blue no matter who.” It’s about “#BlueLivesMatter.”

In an unwittingly communal effort to highlight the surging popularity of socialism, Warren and Biden and Pete and everyone except Bernie already declared they were not socialists. How, then, can we be certain that this is a Mike Bloomberg 2020 hat? How does he stand out in a field crowded with centrists and center-leftists? Well, just like with a North Face down jacket—which, incidentally, would also go great with this cap—the branding is on the back. Weirdly, you would only get the message after the hat wearer has passed you by on the street. Is the hat meant to evoke l’esprit de l’escalier? Does its meaning hit you with a slight delay—not socialism, must be barbarism—eventually leading you, almost subliminally, to the Team Bloomberg Twitter account? Or maybe so many of these non-Bernie bros wear their caps backwards that the back is the front? Or maybe, just maybe, this is something one doesn’t want to talk about face to face? I think that might be it, because this is where Mike tells us, or the back of the hat tells us, to BRING IN THE BOSS.

Bring in the boss only sounds good to people who don’t have a boss, which is probably why Bloomberg thought it was a good slogan. I don’t even think bosses like it when you bring in the boss. The people who might have mentioned this to Bloomberg have him as a boss, so it would have been awkward to bring up. Similarly, it might have been hard—job-endangering, even—to explain the existence of Bruce Springsteen to the mayor, and why that New Jersey not-even-billionaire is, in fact, indisputably, the Boss. But they probably didn’t even show the boss his hat, did they? They probably just came up with something they thought he would like. They brought the boss in mentally because BRING IN THE BOSS is first and foremost a mental state. You keep the boss in the back of your mind at all times, don’t you? So the bad slogan sits there at the back of the cap, poignantly tiny but also in ALL CAPS, a succinct encapsulation of everything that makes Bloomberg such a weak opponent for Trump.

The red MAGA cap is a propaganda masterpiece. Quickly and brightly signaling authoritarianism in the GOP’s signature color, it fuses racism and sexism to patriotism in a four-word phrase whose rhetorical efficiency is unquestionable. (That it’s recycled from Ronald Reagan’s 1980 campaign only underscores that efficiency—Trump eliminated the “Let’s,” so it’s no longer an invitation but a command.) Even though the MAGA cap can be humorously memed—“Make America Mexico Again” is my personal favorite—the accumulation of these variations has only served to underline the original’s power. You are foolish to argue with it directly.

So Mike, at least, didn’t go for that. But what he did go for—neither Bernie nor Donald, but the BOSS—manages to be both beta and basic. Afraid to stand for anything in particular, the slogan argues for a bossy center. Trump, the con man, knows that patriotism gets votes; Bloomberg, the bona fide CEO, believes in corporate enthusiasm. Bernie presents his lofty platform; Bloomberg counters with his lofty social position. Check and mate! Can you imagine becoming the Democratic nominee and soliciting union endorsements with this slogan? How about trying to pass your signature gun legislation by . . . bringing in the boss? Or maybe the environment just needs some bossing around? Or what about all those times Bloomberg L.P. did bring in the boss? His employees were encouraged to affirm a fealty not to the people or to the nation, but to the power of the non-disclosure agreement. So in Bloomberg’s specific case—which this hat undoubtedly asks us to consider—to bring in the boss literally means to bring in the guy who will rob you of all autonomy, harass you, sic his lawyers on you, and threaten to fire you because, say, his banker friends don’t like what you wrote. That times sixty-one billion.

I wanted to preorder the hat, to own the perfect memento from our political hellscape, so I went to peruse the online shop. It wasn’t easy to find. The variety of merch was remarkable, and it was organized in so many different categories that I couldn’t be sure where to click. This hat wasn’t in Hats, which only offered a single solitary winter hat, so I tried Goods, which weirdly only had the same winter hat that was in Hats. Finally, I clicked New Arrivals, but that category was flooded—eight pages of the randomest campaign merch I’ve ever seen, but still no BOSS cap. The effect was of a presidential candidacy on Zazzle. Except that site is trying to make money. This operation is visibly swimming in money. Every idea floats there, equally untethered to any larger political or organizational purpose. Scrolling through the store I felt I truly understood this campaign: everyone working there seems happy to say or design just about anything, as long as they are getting paid. Spending the boss’s money is fun, and it would be funny, too, if they weren’t choking our political discourse with $500 million—and counting—of garbage.

And still, I was undeterred from my desire to own a hat. I decided to click through each category in turn, but the first four listings—All Apparel, AAPI, All, Apparel—really scared me off. I felt bad for Asian Americans and Pacific Islanders for being squeezed into the totalizing philosophical conundrum that is All Apparel, All, and Apparel. I decided to find a direct link to the hat, but as it turns out, that link is now dead. Lingering on the site, my eye was eventually drawn to a black T-shirt in the New Arrivals section. The shirt read ALL ISN’T WELL, in large red letters. I guess he’s running on that now?

  1. For a complementary explanation—unrelated to the semiotics of apparel—see Patrick Blanchfield’s recent piece

  2. For (much) more on the Midtown Uniform, see this Esquire investigation

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