When Weiss Says Sell, Are Insiders Selling Too?

Weiss Ratings just issued a stark warning. On a day when the market was focused on other news, the firm published a data-heavy report giving "Sell" ratings to Boeing, Warner Brothers Discovery, and Cloudflare. The reasons are severe: Boeing's net loss of $9.85 billion over the last four quarters, Cloudflare's negative EBITDA of $48.7 million, and Warner Brothers' sharp declines in cash flow. This isn't a minor downgrade; it's a fundamental indictment of their financial health.

The contrast with Wall Street is jarring. While Weiss is sounding the alarm, the broader analyst community remains overwhelmingly bullish. At year-end 2025, 95% of Wall Street stock ratings on S&P 500 stocks urged investors to buy or at least hold. Only 5% advised selling. This creates a classic double-edged sword for investors. The official rating is a red flag, but it's flying against a tide of institutional cheerleading.

So, what does the smart money think? The critical question isn't about Weiss's analysis-it's about alignment. Do the people with the most to lose-the insiders-agree with this sell signal, or are they quietly accumulating while the ratings are downgraded? For now, the evidence from filings tells us nothing about their current actions. The Weiss report highlights a conflict of interest many investors overlook, but the real test is in the trades. When the ratings are down, do the skin-in-the-game players follow the data, or do they see a buying opportunity the ratings miss? That's the setup for the next move.

Insider Skin in the Game: The CEO's Wallet Tells the Real Story

The Weiss sell signal is a headline. The real story is in the trades. When the ratings are down, do the people with the most to lose-the insiders-agree with the data, or are they quietly betting against the company? The filings show a clear pattern of selling, not buying.

At Cloudflare, the signal is immediate and massive. On January 8, CEO Matthew Prince led a wave of 13 stock sales, totaling nearly $10 million. This wasn't a minor adjustment; it was a significant cash-out. The activity wasn't isolated to Prince. Other insiders were also active sellers in recent weeks, creating a coordinated exit. This is the opposite of the "skin in the game" alignment that signals confidence. When the CEO is selling while the company faces a Weiss "Sell" rating, it raises a red flag about future prospects.

Warner Brothers Discovery shows a similar, long-term trend. The company's CEO and CFO have been active sellers in recent months. Most notably, the CFO's sales alone exceeded $20 million in December. The broader insider sentiment score for the company is 49, which is near the average. This indicates no significant accumulation by corporate insiders. In other words, the people running the company aren't stepping up to buy shares when the ratings are down. Their actions suggest they see value in cashing out, not in betting on a turnaround.

Boeing presents a different picture, but it's not one of bullishness. Insiders reported 11 award transactions on January 2, all for Phantom Stock Units valued at $0.00. This means no direct stock was bought. The transactions were for phantom units, which are typically part of compensation plans and don't represent a personal investment. In a company with a net loss of $9.85 billion, this lack of direct buying from insiders is telling. It shows no insider is putting their own money on the line to support the stock.

The bottom line is that the smart money is not following the Weiss signal to buy. It's following it to sell. Whether it's Prince's $10 million exit at Cloudflare, the CFO's $20 million cash-out at Warner Brothers, or the complete absence of insider buying at Boeing, the message from the filings is consistent. When the ratings are down, the insiders are getting out. That's the real signal.

The Smart Money Trail: Institutional Accumulation vs. Panic

The CEO's wallet is the first signal. But the real test is whether the smart money-the big institutional players-is following the same path. For that, we look at 13F filings, which show the buying and selling by large funds. The evidence here is thin for our three companies, but the pattern of insider sales tells us what we need to know.

The bottom line is that there's no sign of institutional accumulation. In fact, the coordinated exits by top executives at Cloudflare and Warner Brothers are the opposite of what you'd see if smart money was stepping in to buy. When the people running the company are cashing out, it's a powerful signal that the fundamentals are under pressure. It suggests they see value in the cash, not in the stock.

This lack of insider buying, even during periods of low stock prices, is a bearish signal for long-term value. As Peter Lynch famously noted, insiders buy shares for only one reason: they think the price will rise. The silence from the top is deafening. At Cloudflare, the CEO's $10 million sale on January 8 was a major event. If institutional investors were seeing a buying opportunity, you'd expect to see some accumulation to counter that selling. The absence of that counter-move is telling.

The smart money trail, therefore, points to panic, not accumulation. The filings show insiders getting out, not in. That's the real signal for investors to watch. When the people with the most to lose are selling, it's a red flag that the smart money is likely to follow.

Catalysts and Risks: What to Watch Next

The thesis here is clear: insider pessimism is the dominant signal. The near-term catalysts are all about confirming or contradicting that view. The most direct test will be future 13F filings from major funds. If institutional accumulation begins to counter the insider selling, it would suggest the smart money sees value where insiders do not. The absence of that counter-move, however, would validate the bearish setup. Watch for any significant new positions or large-scale buys in the coming months.

For Boeing and Warner Brothers Discovery, the key data points are the upcoming earnings reports. These will provide the hard numbers to see if the financial deterioration cited by Weiss is accelerating. For Boeing, the focus will be on cash flow and any progress toward turning its net loss of $9.85 billion into a profit. For Warner Brothers, the reports will show whether the sharp declines in earnings growth and cash inflows are stabilizing or worsening. Any further deterioration would confirm the Weiss sell case and likely pressure the stock further.

The primary risk to the thesis is that the insider sales are for personal financial planning, not a bearish signal. Executives often sell to diversify portfolios or fund personal expenses. The scale and timing of the recent sales, however, warrant scrutiny. At Cloudflare, CEO Matthew Prince's $10 million sale on January 8 was a massive, coordinated event. At Warner Brothers, the CFO's sales alone exceeded $20 million in December. This isn't routine portfolio management; it's a significant cash-out by key insiders. If these sales are purely personal, it raises questions about their long-term commitment to the companies they lead.

The bottom line is that the smart money is not buying. The catalysts ahead will test whether that pessimism is justified by the numbers or if it's an overreaction. Watch the filings and the earnings for the next move.