Car wrecks and wrecked education, new wardrobes and crewed yachts, working sump pumps and rich relatives, plus one unique robot figure prominently in lottery proceeds.

Chances are most people have considered what they would do with proceeds from winning the lottery, whether or not they play along by buying tickets.

Some no doubt envision using the money wisely, donating to those working to end war, stop world hunger, or advance medical breakthroughs. Others perhaps would go on personal spending frees, winding up with material goods well out of their reach under their normal circumstances. Where would you fall, investing in the endeavors of humanity or jetsetting around the world, leaving it all behind? The intrigue is all in the imagining.

For the annual winner literary issue, The Monthly solicited essay submissions from Bay Area writers on the theme, “If I Won the Lottery.” Essayists approached the topic straightforwardly, a little sideways, and, in a way, not at all, making for interesting and thoughtful prose. The essays presented here cover the notion of richness with insight and humor, lighthearted wit and poignancy.

Thanks to all those who submitted essays for consideration. And for those who did not, you’ll have another chance to send in essays, because The Monthly orchestrates essay contests twice a year. If you have an idea you think could work as a theme, send it to Editor@TheMonthly.com.

Winning Big
Sometimes the real treasure isn’t money at all. By Stacy Appel.

Hedging My Bets
A teacher down on gambling with education daydreams a little. By Melody Ermachild Chavis.

Once Upon a Dress
A decided non-clotheshorse reflects on school uniforms, a crazy skirt, and the notion of ignoring price tags. By Kathy Hrastar.

The Worrying Never Ends
Sump pumps and new roofs top a single mom’s wish list as threats from global warming and El Niño occupy her thoughts. By Carolyn Jones.

Some Like It Rich
Fantasies of a yacht and crew in the Caribbean seep into notions of the former voice of the California lottery. By Robert Menzimer.

This
An exercise in how to get the dough leads to an inexpensive but priceless ending. By Maureen Ellen O’Leary.

Buy Now; Beat the Rush!
A daughter motivated to improve her elderly mother’s failing health thinks up a clever invention. By Nancy Silver.