PROP director reports tax share withholding, conversions
Prairie Operating Co. director Jonathan H. Gray reported several administrative equity moves, led by a tax-related share withholding.
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Form Type
4
Rhea-AI Filing Summary
Prairie Operating Co. director Jonathan H. Gray reported several administrative equity moves, led by a tax-related share withholding. On June 4, 2026, 15,544 shares of common stock were withheld at $0.87 per share to cover tax obligations upon vesting of restricted stock, leaving him with 660,273 directly held shares. Earlier, on April 20, 2026, entities First Idea International Ltd. and First Idea Ventures LLC, through which Gray has indirect holdings, recorded "other" transactions in common stock and Series D Convertible Preferred Stock linked to preferred stock conversion agreements, without open-market buying or selling.
Insider Trade Summary
5 transactions reported
Mixed
5 txns
Insider
Gray Jonathan H.
Role
Director
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise Price or Tax Liability | Common Stock | 15,544 | $0.87 | $14K |
| Other | Series D Convertible Preferred Stock | 720 | $0.00 | $0.00 |
| Other | Series D Convertible Preferred Stock | 254.87 | $0.00 | $0.00 |
| Other | Common Stock | 396,901 | $1.81 | $718K |
| Other | Common Stock | 140,497 | $1.81 | $254K |
Holdings After Transaction:
Series D Convertible Preferred Stock — 30 contracts (Indirect, Held by First Idea Ventures LLC);
Series D Convertible Preferred Stock — 0 contracts (Indirect, Held by First Idea International Ltd.);
Common Stock — 627,060 shares (Indirect, Held by First Idea Ventures LLC);
Common Stock — 300,496 shares (Indirect, Held by First Idea International Ltd.);
Common Stock — 660,273 shares (Direct)
Footnotes (3)
- F1. Prairie Operating Co. (the "Company") entered into preferred stock conversion agreements with certain holders of its Series D Convertible Preferred Stock, including First Idea Ventures LLC and First Idea International Ltd., pursuant to which, among other things, the shares of Series D Convertible Preferred Stock held by such holders were converted into shares of the Company's common stock, par value $0.01 per share, upon the terms set forth therein.
- F2. Represents shares that were withheld upon vesting of restricted stock to satisfy tax withholding obligations.
- F3. The Series D Convertible Preferred Stock has no expiration date.
Key Figures
Tax-withheld shares: 15,544 shares
Tax withholding price: $0.87 per share
Direct holdings after event: 660,273 shares
+5 more
8 metrics
Tax-withheld shares
15,544 shares
Common stock withheld for tax at $0.87 on June 4, 2026
Tax withholding price
$0.87 per share
Price used for 15,544 withheld common shares
Direct holdings after event
660,273 shares
Common stock directly held after June 4, 2026 withholding
First Idea International common
140,497 shares
Common stock in "other" transaction at $1.81 on April 20, 2026
First Idea Ventures common
396,901 shares
Common stock in "other" transaction at $1.81 on April 20, 2026
First Idea International preferred
254.87 shares
Series D Convertible Preferred Stock adjusted on April 20, 2026
First Idea Ventures preferred
720 shares
Series D Convertible Preferred Stock adjusted on April 20, 2026
Conversion price
$5.00 per share
Series D Convertible Preferred Stock into common stock
Key Terms
restricted stock, Series D Convertible Preferred Stock, tax withholding obligations, other acquisition or disposition, +1 more
5 terms
restricted stock financial
"Represents shares that were withheld upon vesting of restricted stock to satisfy tax withholding obligations."
Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.
Series D Convertible Preferred Stock financial
"holders of its Series D Convertible Preferred Stock, including First Idea Ventures LLC and First Idea International Ltd."
Series D convertible preferred stock is a class of shares issued in a later-stage funding round that gives holders priority over common shareholders for payouts and often a fixed dividend, while including an option to convert those shares into common stock. It matters to investors because it affects who gets paid first if a company is sold or liquidates and can change ownership stakes and voting power when converted, similar to holding a safer ticket that can be exchanged for regular tickets later.
tax withholding obligations financial
"withheld upon vesting of restricted stock to satisfy tax withholding obligations."
other acquisition or disposition financial
"transaction_code_description": "Other acquisition or disposition""
conversion agreements financial
"entered into preferred stock conversion agreements with certain holders of its Series D Convertible Preferred Stock"
A conversion agreement is a contract that lets one form of investment — such as a loan, preferred shares or warrants — be changed into another, most often common stock, under set conditions like a price or date. For investors it matters because conversion changes who owns what and how much — similar to exchanging a coupon for a product — which can lower a company’s debt, increase the number of shares (dilution), shift control and alter future returns and valuation.
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What insider transactions did Jonathan H. Gray report for Prairie Operating Co. (PROP)?
Jonathan H. Gray reported tax-related and restructuring equity transactions. A key item was 15,544 common shares withheld to cover tax obligations, plus several "other" transactions involving common and Series D Convertible Preferred Stock held through First Idea International Ltd. and First Idea Ventures LLC.
Was the June 4, 2026 PROP Form 4 a stock sale by Jonathan H. Gray?
The June 4, 2026 entry was not an open-market sale. It reflects 15,544 common shares withheld at $0.87 per share to satisfy tax withholding obligations on vested restricted stock, a standard non-discretionary mechanism rather than a voluntary sale into the market.
What is the role of First Idea International Ltd. and First Idea Ventures LLC in PROP’s Form 4?
First Idea International Ltd. and First Idea Ventures LLC hold Prairie Operating Co. securities indirectly for Jonathan H. Gray. On April 20, 2026, both entities recorded “other acquisition or disposition” transactions in common stock and Series D Convertible Preferred Stock tied to preferred stock conversion agreements.
Does the PROP Form 4 suggest significant directional trading by the insider?
The Form 4 primarily shows a tax-withholding event and several restructuring-type transactions. There are no open-market purchase or sale codes reported, and the tax withholding involves a relatively small portion of Gray’s 660,273 directly held common shares.
AI-generated analysis. How Rhea-AI works. Not financial advice.
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