Tales of a Win/WIN Strategist

Bill and Dean in Bill’s courtroom

My brother Bill was always looking for a win/WIN, with the capital WIN belonging to him.

He was in a prime position for that WIN. Being the oldest of 10 children automatically gave him some status. If you think about it, he was the sole sibling who had had undivided attention for any period of time—granted, it was only 16 months before the next birth, but it was something. He also had more time to think about how to manipulate us.

By nature, he was not heavy-handed, more apt to use his wits to take advantage of us.

In 1953 Bill became a paper boy in Tucson, AZ.

A refresher on how paper routes worked: a man would drop off a bundle of newspapers on the front porch of the paper boy’s house (no such things as paper girls). The paper boy would fold the papers, secure them with a rubber band and then stuff them in a two sectioned bag that schlepped over the back fender on his bike. Then he tossed papers on driveways—a typical route covered between 60-70 home deliveries. Once a month the paper boy would knock on customers’ doors and collect money for the papers. Sometimes, he had to go back multiple times. Deadbeats were around in the 50’s too. If they didn’t pay up, the paper boy lost a customer—and that loss affected his income, which was about a nickel a day for each paper delivered.

Then, once a month, the guy from the newspaper would come and collect this money from the paper boy. In Bill’s case that was sometimes a problem: he did not always have enough money to pay him and he would have to borrow from my parents. Two things contributed to this occasional short fall: 1. Every day he treated himself to a milkshake at the Dairy Queen that was at the end of his route.  2. His siblings stole from him regularly. Who could blame us? Besides the quarter a week we had for allowance, Bill’s paper route was our only source of income. The worst thief—and she had a lot of competition for this title—was Kathy, who was often found at the local mom and pop store a few blocks away, eating a candy bar on the front stoop.

Bill’s paper route story reveals his resourcefulness, his ability to manipulate us, and his desire to achieve a win-WIN.

For the first few months of his paper route, Bill made us feel that the arrival of the papers was the highlight of the day. We would rush out to help him fold the papers-at least for a while. About six months into his job, most of us had lost interest. Except for Dean, Bill’s younger sibling by a few years. Dean loved to accompany Bill on the route and learned it quickly. The payoff for Dean was not only spending time with his much-admired brother, but the milkshake Bill bought him at the end of the route. That was Dean’s only payment and at the age of 8, I guess it was enough.

Every few months, though, Bill tired of the route and feigned sleep when the papers came. Now mind you, the papers came about 4 in the afternoon, so taking a nap at this time in our house was somewhat improbable and unbelievable. Dean would come into the bedroom they shared and try to rouse Bill from sleep. “Bill, the papers are here. Bill, the papers are here.”  No matter what he did—and he did plenty—like shaking Bill’s shoulders, shouting directly into his ear, and sometimes throwing cold water on him—he couldn’t awaken his brother. As a last resort, Dean would tell Mom, who was pretty clueless about siblings’ torments. She was an only child, and like the 19^th century novels she loved, she only believed in resolutions and happy endings.  Mom would say, “I guess you’ll have to deliver the papers yourself today, Dean.” So Dean would. Without his buddy. And without the milk shake.

Bill was careful to do the feigning infrequently. You don’t really want to mess up a good thing.

So began the lifelong friendship between two brothers and Dean’s lifelong love of milkshakes.

Overall, Bill’s paper route was a win-win for both brothers. Bill became a master at overseeing wins–whether he was dealing with his siblings–or years later with plaintiffs in his courtroom. He became a judge.