The long pass

John Dewberry has grand plans for Midtown, but his timeline remains elusive.
Quarterback-turned-developer John Dewberry

Quarterback-turned-developer John Dewberry

He couldn’t shake it. He, John Dewberry, lost.

Even at 8 years old he knew how to view second place: first among losers.

He was athletic, and he knew how to tussle. He’d powered through football knockabouts in his parents’ suburban Virginia yard. But he was new to team swimming at the neighborhood pool. New, in fact, to any organized sport and its hierarchy of winning.

Mom had resisted such brutish pursuits for him and his older brother. She’d steered her boys to excel at floral arranging instead — even signed them up for contests through 4H.

Once freed to swim competitively, he did well the first couple meets. Then, from across town, came a big kid, a fast one. Dewberry was introduced to defeat.

That evening, he was moping around the house dejected when his father, a former boxer with a competitive streak, found him.

You want to win? he asked his young son.

Yes, the child replied.

The father laid out a plan: Run two miles each morning. Go to summer swim practice. Run another three miles each evening.

Every day the son ran back and forth to his elementary school while the father rode his bicycle alongside. Eventually, the boy swam against the big, fast kid again. This time, he won easily in all but one event.

Why do you think you won? the father asked.

Now, nearly 44 years later, Dewberry’s voice uncharacteristically softens, echoing that of an 8-year-old boy. “I think, Daddy, I felt like I deserved to win because I had worked so hard.”

The lesson became an unshakable truth: Confidence and hard work make winners.