Dear Reader,
They declared a ceasefire!
Until they didn’t.
Then Trump said we were about to sign a deal.
Until we started shooting at each other again.
According to one source, Trump has said an Iran deal is “close” 38 times since the war began.
In the time between writing this message and you reading it, who knows whether we’ll be hearing about an imminent deal… or more bombing.
And it doesn’t matter.
This is all a distraction.
Here’s the REAL reason why Trump may NEVER end this war.
To your future,
Addison Wiggin
Founder, Grey Swan Investment Fraternity
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Oracle Bounced 5% and a Director Bought $3.5M of the Stock. Here Is What That Means.
The most useful thing about Friday’s Oracle session is not the 5% recovery. It is the question the recovery forces you to ask: what exactly changed between Thursday’s close at $135.69 and Friday’s open?
Oracle closed at $135.69 on Thursday, down 5.48 percent, after the Financial Times reported that OpenAI’s annualized revenue was approaching $50 billion at end-September, roughly $20 billion below the figure that had circulated late last month. OpenAI told investors it hit roughly $50 billion in annualized revenue at the end of September, lower than the roughly $70 billion figure that had circulated previously. Reporting around the discrepancy said the higher figure reflected a different accounting presentation that included partner-related gross revenue, which investors had been using to compare more directly with Anthropic. In other words, Thursday’s plunge was a reaction to a number that was never quite what it seemed.
Oracle stock rose 4.76% to $141.62 on Friday as new AI products, a data center update, and bullish analyst coverage supported a rebound. Three things drove the reversal. Oracle announced Oracle Fusion Claw, a governed AI execution runtime for Oracle Fusion Agentic Applications, alongside 25 Claw-powered agentic applications. Oracle Financial Services also launched Oracle Nexus Case Flow and Oracle Nexus Reach, agentic AI tools built to assist financial crime investigations and compliance workflows. Oracle also issued a public statement affirming that its Project Jupiter data center campus in New Mexico remains on schedule and that the company is “fully committed to New Mexico,” pushing back on the prior day’s headlines about permitting and timeline risk.
Adding further fuel to the rebound, Mizuho elevated Oracle to the top spot on its October Top Picks list, setting a $320 price target, roughly 25% above the Bloomberg consensus. Mizuho also highlighted financing and margin risks tied to Oracle’s AI data center expansion. A $320 target sitting 25% above consensus is a headline-grabbing call, but it comes with real financing risk attached. Disciplined traders read both halves.
The most instructive data point of the session arrived from the SEC filing queue. On September 29, Oracle director Stephen Rusckowski purchased 25,000 shares at an average price of $139.352, totaling approximately $3.48 million, according to an SEC Form 4 filed October 1. Rusckowski, the former CEO of Quest Diagnostics, joined Oracle’s board in November 2025. His September transaction represents his first reported open-market purchase since joining the company. The purchase is notable in scale relative to his existing position, since the 25,000 shares acquired represent nearly all of his 25,390-share total holding.
Other Oracle insiders have been net sellers recently, creating a more mixed picture of insider sentiment despite Rusckowski’s sizable vote of confidence. That asymmetry matters. A single director buying into a slide is a signal worth tracking, not a green light. Insiders have informational advantages about company operations, not about how a crowded AI trade unwinds on a bad news cycle. The timing places Rusckowski’s bet squarely in the middle of an ongoing Wall Street debate about how Oracle plans to finance its AI datacenter expansion. That debate has kept pressure on the stock, which makes the willingness to commit $3.5 million at these levels a data point investors will be weighing carefully.
The next test is whether Oracle can monetize its huge AI backlog fast enough to cover the financial costs of building up the infrastructure needed. Friday’s bounce restored none of the year’s losses. Oracle stock is down about 30% this year amid the AI infrastructure build-out, while capital spending was $28.5 billion in the three months ended August 31, 2026, up from $8.5 billion in the same quarter a year earlier.
The Trader’s Lesson: Insider purchases confirm conviction, not timing. When a director spends $3.5 million of personal capital on a beaten-down name, it is worth adding to your research file. It is not a trade signal by itself, and it tells you nothing about when an overhang resolves. The real work is figuring out whether the concern that drove the slide, in this case the sustainability of AI demand from Oracle’s largest customer, has structurally changed or simply paused. Friday’s bounce suggests the market decided Thursday’s move overshot. Whether that judgment holds depends on information that no Form 4 can supply.