Checkbook Bob

Checkbook Bob

A Story of Debt, Dignity, and the Endurance of Paper

By: Mason Absher

There’s a guy in my life—

a legend, really—

named Bob.

But not just any Bob.

CheckBook Bob.

Bob pays with checks.

Exclusively.

Religiously.

He’s never used Venmo.

He once referred to PayPal as “cybercrime.”

And Zelle?

He said, “That sounds like a Marvel villain.”

He pays the old-fashioned way—

with a checkbook.

Worn, leathery, and always within reach.

Except…

Bob’s check hand?

Apparently, it’s injured.

He calls it “a lifelong condition.”

A “financial affliction.”

He says,

“I can only write checks on even-numbered Tuesdays, during a full moon, if the wrist is loose and the Lord is willing.”

Now, to be clear—

I’ve seen Bob fix his roof.

Haul lumber.

Throw a baseball 40 feet underhand at a church picnic.

But ask him to write a check on the spot?

Suddenly his wrist goes limp.

His fingers seize.

He becomes a tragic figure from a Tennessee Williams play.

He once whispered to me at a hardware store,

“The tendons, they just won’t track unless I warm up first.”

Then he flapped his hand like a baby bird and walked away humming the theme to Matlock.

It’s not that Bob won’t pay.

He will.

Eventually.

He just has… a rhythm.

A system.

A… let’s call it what it is:

A bureaucracy of one.

He carries his checkbook in a zippered pouch

wrapped in what I believe is a Maple Leafs windbreaker from 1994.

The pen?

Always a promotional one from a real estate agent who’s long since retired.

One time—this is true—

he owed me $9.60 for pancakes.

He wrote a check.

Tore it carefully from the pad.

Handed it to me like he was bestowing land rights.

And in the memo line?

He wrote:

“For syrup and good company.”

The check bounced.

Temporarily.

(Beat. Performer shrugs.)

But the sentiment cleared.

Bob is not a scammer.

He’s not cheap.

He’s just… committed to a dying craft.

A fiscal artisan.

CheckBook Bob doesn’t pay you.

He memorializes the transaction.

He still owes me $19.87 for movie tickets.

That was in 2019.

But every time I see him, he says:

“I’m working on it.

Just waiting for the tendons to trust me again.”

I believe him.

Because when that check comes?

It’s going to be beautiful.

Signed with a flourish.

Folded into thirds.

Memo line reading:

“For entertainment, popcorn, and brotherhood.”

And I will cry. 

CheckBook Bob.

Long may he write.