Poor John Boehner.

Thanks to a Republican amendment to the Affordable Care Act, most members of Congress will see their government-provided health insurance lapse at the end of the year, leaving many of them no other choice but to enroll in dreaded Obamacare.

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As speaker of the House, Boehner is technically exempt from the requirement, but in order to avoid accusations of special treatment (i.e., because of politics) he decided to take the plunge, too. And he wants you to know how difficult it was. He even wrote a blog post about it.

"Earlier this afternoon, I sat down to try and enroll in the DC exchange under the president’s health care law," he wrote. "Like many Americans, my experience was pretty frustrating. After putting in my personal information, I received an error message. I was able to work past that, but when I went to actually sign up for coverage, I got this 'internal server error' screen": [Here he embedded an image of an internal server error screen.] Despite multiple attempts, I was unable to get past that point and sign up for a health plan. We’ve got a call into the help desk. Guess I’ll just have to keep trying …"

It's a bummer Boehner got that error message. Tyranny almost. But if he'd reached the point at which he was signing up for coverage, it means he'd already had a chance to shop around and pick a plan. His post is oddly quiet about that part of the experience. Which is curious. As a 64-year-old heavy smoker, it's a marvel Boehner will be able to purchase individual market coverage at all. I wonder what crazy law guarantees that he can?

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At any rate, since he didn't disclose which plan he'd settled on, or what his options were, I thought I'd try to re-create his experience for you. So on Thursday night I possibly perjured myself, and created an account on D.C.'s health insurance exchange for a nonexistent 64-year-old man seeking individual coverage.

Because he's shopping on the D.C. exchange, and not in Ohio under Healthcare.gov, I am assuming that his wife, Debbie Boehner, a real estate agent in suburban Cincinnati, has her own coverage, and so he's not purchasing a spousal plan.

It turns out, Boehner, who as speaker makes $223,500 a year, has a lot of affordable options to choose from.

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The cheapest policy for a 64-year-old is a high-deductible, bronze-plated BlueCross BlueShield plan with a $372.14 premium.

Just under 2 percent of Boehner's income. Not bad for a man on the cusp of his golden years!

Now Boehner just had a birthday, so in less than a year he'll qualify for Medicare. If I were him, I'd probably take my chances with a cheap plan like this one and pocket the savings for my retirement, which could come as early as January 2015. Who's to say?

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Then again, Boehner has a stressful job, and that smoking habit. Plus, his net worth is in the low millions. Under the circumstances (and since he'll only be enrolled for a year anyhow) it might be worth it for him to purchase something more expensive.

I counted five $0 deductible plans (three gold-plated, two bronze-plated) ranging in price from $699.86 a month -- or 3.7 percent of Boehner's annual income ...

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... to $1,023.28 per month -- or a heftier 5.5 percent of Boehner's annual income.

That was the most expensive option available, by nearly $200 a month.

If he'd decided to enroll in Ohio, his options would be generally cheaper. The plans available in Butler County, where he resides, start at just $203.51 a month for a 64-year-old, or 1.1 percent of his annual income. Given the potential savings, I assume his decision to enroll in D.C. reflects a high degree of confidence that he won't be run out on a rail by conservative hard-liners before the next Congress begins (at which point, he'll be eligible for Medicare anyhow).

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Boehner's actual premiums will likely be somewhat higher due to that smoking habit. Smoking's actually the only thing insurers are allowed to underwrite for. The fact that members are allowed to shop in the small group market might affect his options and prices somewhat too. From there, though, his costs could be dramatically offset by an Obama administration rule that allows members to carry the federal government's contribution to employee premiums into the exchange. Presumably, even if he's eligible, Boehner will decline the contribution to avoid a political backlash (though he fought hard behind the scenes to preserve it for all members). But this gives us a decent sense of the horror show he encountered Thursday, before he encountered that even more horrible error message.

I understand how frustrating error messages can be for the elderly. And at first I assumed that what had ultimately derailed Boehner's quest for coverage was a severe case of Acute Technological Grandpaism (ATG). Befuddlement at the sight of error messages is one of the most common symptoms of ATG.

But then I thought about it some more and realized it didn't really fit the facts.

First of all, there was at least one other person in the room with Boehner at the time: the photographer. Whoever that person was is savvy enough with electronics to snap digital photos. So there's that. But also, the pictures reveal that he went searching for coverage from his Capitol Hill office. And I know from experience that Boehner is surrounded every day by a staff that's chock-full of smart, tech-savvy youngsters. His website is one of the best on the Hill! Much better than Healthcare.gov.

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So then I figured either the D.C. exchange is really, really broken, or he didn't actually think through his cheap shot very well. And indeed, while I was writing this article last night, shortly after his blog post went live, a breakthrough.

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Congratulations, Speaker Boehner. To your health.