In the conversation above, the remark is used as a dodge -- Hewitt asks what Steyn thinks about normalizing the status of those here illegally, and Steyn avoids giving a direct answer by launching into a familiar riff. But Steyn is also adeptly telling the audience a story that plays to their prejudices. The older white conservatives who buy Steyn's books and listen to Hewitt's show hear an echo of a narrative that many have long told themselves about illegal immigrants. In their view, conservatives shell out their hard-earned money to pay their income taxes, their property taxes, their vehicle license fees, their auto-insurance premium, and their health-insurance bills, playing by all the rules, being responsible citizens ... only to have "these illegals" come into the country without permission, get paid under the table, get free care at the emergency room when they get the flu, and victimize law-abiding Americans when they rear-end them at a stop sign and flee because they're driving around without any auto insurance.
I've heard numerous conservatives, none of them poor, working class guys in stiff competition with illegal immigrants for jobs, claim that they are actually envious of illegal immigrants. This is our country, they'll say, and they've got it better than we do. Can you imagine what would happen if I was paid off the books / if I got pulled over by the cops and I didn't have a driver's license to show / if I went to the hospital and couldn't pay my bill / if I tried to enter their country illegally?
Of course, none of these people would ever dream of trading places with an illegal immigrant, as they'd surely realize if they gave the subject very much reflection, which they don't. It's disappointing that Steyn traffics in such unoriginal, thoughtless material these days, for he surely knows better. Even if he doesn't, it sounds particularly absurd for an exceptionally successful, well-traveled, relatively rich conservative demi-celebrity to deliver this schtick. Only someone who knows nothing about what it's like to be an illegal immigrant "living in the shadows" could listen without rolling their eyes to Steyn feigning envy of "living in the shadows."
It doesn't work even as a joke -- the premise is nonsense.
On a factual level, of course legal immigrants can send remittances back to their home country. Many do!
On a more visceral level, when I hear Steyn's schtick about how he'd prefer to live in the shadows, and he doubts many illegals want to come out of them, I think about all the people I've interviewed who were terrified that their undocumented status will cause them to be fired from their jobs, or separated from their children, or thrown into a nightmarish federal detention facility, people who would literally cut off a finger if in exchange they could be an American citizen.
I can only imagine how Steyn's "I'd prefer the shadows" schtick sounds to the subset of Hispanic and Asian-American voters who have personal contact with immigrants of all kids and understand what it's really like to be an illegal immigrant, as opposed to the pretend talk radio version of how easy they have it. I don't mean to imply that Steyn sounds racist. To me, he just sounds clueless, insensitive, and self-pitying. (Sort of like how Lawrence O'Donnell seems clueless and insensitive in this interview). Given the chance to immigrate legally to the United States, a privilege many would regard as akin to winning the lottery, one of Steyn's most frequent reflections is that he envies illegal immigrants because they face less scrutiny from the IRS!
One needn't embrace any particular position on immigration to acknowledge how difficult life is for so many people who are here illegally. Doing so signals to voters that you've got a basic grasp on reality and possess normal levels of human sympathy. Whereas a rich immigrant from Canada talking like he's got it tougher than "the illegals" .... I mean, really, do I need to explain why that is off-putting? Why it signals to voters a disconnect with reality? It's possible to win Hispanic votes while opposing amnesty. But winning Hispanic votes when you mostly treat illegal immigrants as conceits to invoke during anti-IRS rants that you deliver on talk radio? Probably a losing strategy. And one that reinforces the belief among many talk radio listeners that illegal immigrants really do mostly have it easy in America, easier even than the listeners themselves.