Volume XLIV

I. Ballpark Estimate 🏟️

Before advanced analytics, Statcast, or laser tracking, baseball had no exact measurements. A home run’s distance was judged by which ballpark it landed in, not the down-to-the-inch measurement we get today.

In the early 1900s, businessmen borrowed the phrase to mean a rough estimate that landed in the right range, even if it wasn’t precise.

Nowadays it’s more commonly used when parents try to get an idea of when their kid will be home as he heads out the door with ‘vague’ plans.

II. Robbing Peter to Pay Paul 💰

The phrase comes from medieval England, when money set aside for St. Peter’s church was redirected to support St. Paul’s. One church gained, the other lost, and no new money ever showed up.

It’s the same idea as that guy in college who texted every couple of weeks on Friday night asking for a $20 loan, promising to pay you back $25 on Monday. No job, no plan — just money moving around so he could buy something he couldn’t afford.

III. Well-Heeled 👞

Before it meant money, it was related to shoes. Good heels signaled quality leather, recent repairs, and enough spare cash to keep them that way. Worn-down heels meant long walks, hard labor, and no cobbler in sight.

By the 18th century, the pattern was obvious: people with intact heels usually had intact lives and the phrase slipped quietly from footwear to finances.

Today, well-heeled is a polite, faintly old-fashioned way of saying someone has money. You don’t ask how they got there but you can tell by the shoes.

Keep on sending on. Forward to a friend.