Jackson Hollow Investments LLC v. Desmond Mason

Let’s cut straight to the chase: a tenant tried to pay his rent with three separate $8,000 checks — one for “Effort & Performance Report,” another made out to “Chris Conway” (or possibly “Chry Coyner,” depending on your handwriting interpretation), and a third for $16,000 marked “Horse Rent” — and every single one bounced. Not just declined — returned, dishonored, dead on arrival. We’re not in Landlord-Tenant Court anymore; we’re in theater.

So who are these characters? On one side, you’ve got Jackson Hollow Investments LLC — a name so generic it sounds like it was generated by a real estate AI trained on tax loopholes and property deeds. They own a residential property at 2600 NW 57th Street in Oklahoma City, which, according to Google Maps, looks like your average suburban duplex that’s seen one too many questionable tenant decisions. Representing them is James Clay Condry, Esq. — yes, that Clay Condry, the one whose name appears both as the attorney and the manager of the LLC, which raises the question: is this a law firm or a side hustle with a notary stamp? Either way, he’s now personally posting eviction notices on doors like some legal UPS guy.

On the other side: Desmond Mason, the man, the myth, the bouncing check legend. What kind of person writes an $8,000 personal check labeled “Effort & Performance Report” as if they’re invoicing their landlord for emotional labor? Was this a performance review? Did he expect a bonus? And why was the check made out to Clay Conary — a name that’s either a typo, a pseudonym, or the secret identity of our attorney? We may never know. But one thing’s clear: Mason wasn’t just behind on rent. He was performing delinquency.

Here’s how the drama unfolded. Mason had a lease. He moved in. All normal. Then came the rent payments — or, more accurately, the attempts at rent payments that played out like a series of increasingly desperate improv scenes. First, on January 20, 2026, he hands over an $8,000 check drawn on Armstrong Bank, memo line proudly declaring “Effort & Performance Report.” Let’s pause. That’s not a rent check. That’s a consulting invoice. Did he think he was being paid by the landlord for being a tenant? Was he billing for “occupancy services”? The mind reels.

The bank, unimpressed by his corporate jargon, returned the check on January 23 with the cold, mechanical finality of “Return Item.” Debit: $8,000. Credit: zero dignity. Mason’s account? Plunged to -$6,561.24. That’s not a bank balance — that’s a cry for help.

Undeterred, Mason tries again. On February 14, another $8,000 check surfaces — this one made out to “Chris Conway” (though the signature says “Drisdon J. Nickson,” and the address is for a building on Northwestern Ave, possibly a mailbox rental). Same bank. Same amount. Same fate: returned on February 5. At this point, the landlord — or rather, the landlord’s attorney-manager — has seen enough. On February 13, before the second check even officially bounces (Oklahoma banking: where hope dies slow), Condry slaps a Five-Day Notice to Pay Rent or Quit on the front door like a medieval decree. The message is clear: pay up or pack up.

But Mason isn’t done. Oh no. He pulls out the big guns: a $16,000 check from First Fidelity Bank, memo line boldly stating “Horse Rent.” Now, we have questions. Is there a horse on the property? Did Mason sublet to a stable? Is “Horse Rent” code for something? A loan? A gambling debt? A metaphor for the emotional burden of tenancy? The court filing doesn’t say — but the sheer audacity is breathtaking. A $16,000 check for horse rent, written like it’s a line item in a Wild West accounting ledger. And of course, it bounces too. Because of course it does.

By February 20, Jackson Hollow sues. Not for murder, not for arson, but for forcible entry and detainer — legalese for “get out, you’re not welcome anymore.” They want two things: the apartment back, and $17,000 in unpaid rent and charges. Seventeen grand. That’s not just a few months’ rent — that’s years of back payments on a typical Oklahoma City duplex. Even if the monthly rent were $2,000 (which it almost certainly isn’t), we’re talking nearly seven months of nonpayment. And yet, instead of just… paying, Mason chose the path of financial performance art.

So what exactly are they suing for? Forcible entry and detainer — sounds like a home invasion, but in landlord law, it’s the fast-track eviction process. It’s not about whether you owe money in a complex contract dispute; it’s “you’re on my property and you shouldn’t be.” The landlord doesn’t need to prove the full debt here — just that rent is overdue and the tenant won’t leave. The $17,000? That’s the civil side — the money claim tacked on. And get this: the filing explicitly says they’re reserving the right to pursue criminal charges for issuing bad checks under Oklahoma law. That’s right — Mason could go to jail for writing a check labeled “Horse Rent.”

Now, is $17,000 a lot? In eviction court? Absolutely. Most rent disputes hover around a few thousand. This is luxury-level delinquency. That’s a used car, a solid down payment on a house, or, in Mason’s case, apparently enough to fund a small equestrian operation. And yet, given that he’s writing $16,000 checks like they’re Monopoly money, maybe he thought he was above such petty concerns as funds available.

Our take? Look, we’ve covered lawsuits over stolen chickens, feuding HOAs, and divorces fought over Pokémon cards. But this one? This is art. This is a man who didn’t just fail to pay rent — he turned nonpayment into a brand. “Effort & Performance Report”? “Horse Rent”? That’s not negligence. That’s flair. We’re not saying he should get to stay — the landlord deserves their property back, and bouncing checks isn’t a lifestyle, it’s a crime — but can we at least acknowledge the commitment? Most deadbeats just ghost. Mason showed up with paperwork, memos, and a narrative. He didn’t just owe rent — he was redefining it.

We’re rooting for accountability — but also for someone to track down that horse. Because if there’s no horse, then “Horse Rent” wasn’t a payment. It was a metaphor. And honestly? In the grand tradition of Oklahoma civil court absurdity, that might be the most poetic eviction we’ve ever seen.

We’re entertainers, not lawyers. But if this case goes to trial, we’re bringing popcorn — and a saddle.