What Does Winning Look Like?

My mother cared for my father full time in the last three years of his life, making appointments, taking him to doctors, visiting him in the hospital and nursing home. Just then, their health insurance company started sending them letters: pay your monthly premium within two weeks, or your insurance will be canceled. The company’s system would invalidate the credit card used for automatic payment of their premiums. My mother would call the company in a panic.

The nice customer service rep would reapply the credit card, but a month or two later the same thing would happen. Finally, not knowing what to do, my mother asked me to try to fix this. I called two or three times. I explained the problem. I listed the times my mother and I had called and who we spoke to. I would ask them to fix the problem permanently, which they promised to do. But it kept happening.

You can imagine how alarming and frustrating this was—just when our attention was occupied with my father, we had to scramble to deal with a problem caused by the insurance company.

Finally, I wrote a letter to the company’s CEO, explaining the problem, all the times we had to call, and how this affected my parents. That did the trick. The problem was solved permanently. The monthly premiums were charged automatically to the credit card, and the company never threatened to cancel their insurance again.

This episode reveals two lessons Democrats should take to heart. First of all, they have to be clear what winning means. For us, winning didn’t mean getting the insurance premium paid for one month; it meant a permanent fix, getting monthly payments to occur automatically. Likewise, Democrats shouldn’t be satisfied with winning one or two elections. They should aim at winning a permanent majority so that they can implement policies and secure them from being nullified by Republicans.

Republicans losing doesn’t mean Democrats are winning.

If you’re over 50, you probably remember New Coke. In 1985, Coca-Cola retired its signature soda and replaced it with a new formula, New Coke. Coke drinkers refused to buy the product. Sales of rival Pepsi shot up. Coca-Cola retreated, apologizing to customers and restoring classic Coke. Ultimately, the publicity caused sales of classic Coke to go higher than they were before New Coke.

Like the cola market, two competitors dominate American politics. If supporters of one party are unhappy with its performance, they stay home on election day, and the other party, the only alternative, wins. That doesn’t mean the balance of power has shifted. Cokes drinkers didn’t become converts to Pepsi even if they drank Pepsi temporarily. They returned to Coke as soon as the company went back to its original formula. Similarly, the voters who stayed home will come back to the polls eventually.

Remember W.’s disastrous administration? We assumed Republicans wouldn’t nominate a lying, incompetent fool again for president because W. became so unpopular. After Democrats’ big win in the 2006 midterms and Obama’s win in 2008, we believed Democrats had regained a permanent majority. Then came the Tea Party in 2010 and Trump in 2016. After Trump’s first term, we assumed voters had learned their lesson and would never choose him again. Wrong again.

Now we’re expecting a big Democratic win in 2026 and likely a Democratic president in 2028. But just because voters don’t like Trump doesn’t mean they’ve become Democrats. Democrats focused wholly on the next election will pat themselves on the back for their wins and then be stunned when Republicans win big in 2030 and someone as bad as W. and Trump wins the presidency in 2032 or 2036.

Which leads me to the second big lesson from the episode of my parents’ health insurance company: You have to address the right audience with a message that will move them. The customer service reps my mother and I spoke to didn’t have the authority to order the technical staff managing the payment system to make a permanent fix. I needed to reach someone above both the IT department and the customer service department, namely, the CEO. He had the power to make people do what needed to be done to help my parents.

I wrote a letter designed to persuade a CEO. I documented the half dozen times my mother and I talked to customer service and what the results were. I showed the impact on my mother, how she couldn’t afford to take time away from caring for my father. And I said that my father was a combat veteran.

I painted a portrait of my parents’ situation anyone would sympathize with. I showed that the problem couldn’t be solved through the usual channels. If my parents had trouble with automatic payments, other customers probably had trouble, too. So customer satisfaction was at issue. And the company would look bad if my parents’ plight became public. Finally, the appeal worked on the CEO’s vanity—only you can help us (which was true). All of these factors helped the CEO decide that it was worth his time to intervene.

In the same way, Democrats must address the audience that has the power to give them a permanent majority—Republican voters. If Democrats could persuade as few as 5% of Republican voters to switch sides permanently, they would become the majority party. In the middle of the 20th century, Democrats were the majority party. Then a decisive slice of the electorate was persuaded to vote Republican. It’s not as if Americans are genetically programmed to be Republicans. Many Republicans can be persuaded to switch sides…with the right message.

A message that persuades Republicans to become Democrats would not sound like my letter to the CEO of the health insurance company. Republicans respond to different arguments and rhetoric. But like my letter, a message to Republicans will show them why they should switch sides by showing the impact on themselves and what they care about. And a winning message will play to their emotions (if not to their vanity). Democrats will carefully construct their message and pound it home over many years if they want to win in a meaningful way, not just win one or two elections whose results are easily reversed.