President Donald Trump’s latest financial disclosure dropped last month, and one trade in particular is getting the retail-trader crowd talking. On Feb. 10, 2026, Trump bought between $1 million and $5 million of ServiceNow (NOW) stock — right as the software sector was getting steamrolled by fears that agentic AI would gut the per-seat SaaS business model.
NOW stock is down roughly 26% year-to-date (YTD). It’s one of the worst-performing major names in enterprise software — and Trump appears to have stepped in to buy shares on a day the sector was deeply out of favor.
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Trump didn’t stop at ServiceNow. The same filing shows that the president also added Adobe (ADBE), Workday (WDAY), Oracle (ORCL), Nvidia (NVDA), Broadcom (AVGO), Microsoft (MSFT), Texas Instruments (TXN), and Dell Technologies (DELL) in the same $1 million to $5 million band. The disclosure, released by the U.S. Office of Government Ethics on May 14, covers roughly 3,700 transactions in the first quarter, valued between $220 million and $750 million in total.
For investors watching the software wreck unfold, the question is whether Trump picked the bottom — or stepped in front of a freight train that hasn’t finished moving yet.
The Software Sector Has Been Brutal in 2026
The iShares Expanded Tech-Software Sector ETF (IGV) is down roughly 9% YTD as of this writing. That comes amid a sector-wide drawdown, not a single-name story. The damage has been distributed across names, with ServiceNow down 26% YTD, Adobe down 28% YTD, Salesforce (CRM) down roughly 31% YTD, Workday down 32% YTD, and Oracle up 8% YTD but down 39% from its 52-week high.
The fundamental story driving the selloff is straightforward. For two decades, enterprise software ran on a per-seat pricing model, with more employees equating to more licenses. Agentic AI threatens to invert that math. If one AI agent does the work of three salespeople, three customer-service reps, or three IT admins, the seat count goes down — and so does the recurring revenue line that built every SaaS valuation multiple in the modern era.
That’s the bear case in a few sentences. The market has been pricing it in aggressively since late 2025.
April 23 Was the Single-Worst Day for ServiceNow
NOW stock’s drawdown wasn’t a slow grind. The decisive move came on April 23, when shares fell roughly 18% in a single session — the stock’s worst day on record — after Q1 2026 earnings showed on-premise deal slippage tied to the Middle East conflict and broader subscription headwinds. Management narrowly beat estimates but flagged the Iran war as a headwind to forward subscription revenue.
That print is what pushed NOW stock from “underperforming” to “broken.” It’s also what made the stock cheap enough for contrarian buyers to show up. Trump’s Feb. 10 purchase came earlier in the slide, but the sector’s overall selloff thesis was already in motion.
The Contrarian Case Trump Is Buying Into
The bull case on software right now rests on three points.
First, the “AI kills SaaS” thesis assumes per-seat revenue is the entire business. It isn’t. ServiceNow, Salesforce, and Adobe have been actively shifting toward consumption-based pricing, where customers pay for AI agent runs, API calls, or workflow executions rather than per-employee licenses. If that transition lands, the revenue model survives and just gets repriced.
Second, the multiples have compressed enough that the math no longer requires heroic growth assumptions to work. ServiceNow’s customer retention rate remains exceptional, and the company has continued to beat earnings estimates even as NOW stock has been punished.
Third, this is a sector that has traded at a structural premium for a decade. Drawdowns of 30% or more from highs are extraordinarily rare. Mean reversion alone is a real argument, even before you factor in the AI monetization thesis playing out.
The bear case is still intact. Per-seat pricing erosion is real, and the IGV chart hasn’t bottomed. ServiceNow stock could retest lower if Middle East subscription headwinds extend. Plus, buying a falling knife on a politician’s disclosure — released months after the actual trade — isn’t a strategy.
But for investors who think the software selloff has overshot, the names that Trump bought are the same ones showing up on every contrarian buy list right now: NOW, ADBE, WDAY, ORCL. All beaten down. All at multi-year lows. All getting reconsidered by analysts who turned cautious six months ago and are now asking whether the panic is fully priced in.
What Should Investors Watch From Here?
Three things matter for the software trade going forward.
The next ServiceNow earnings report — Q2 2026, expected in late July — will show whether the April subscription weakness was a one-quarter blip or the start of a structural trend. If subscription growth reaccelerates, the contrarian thesis quickly becomes much more credible.
The situation in the Middle East also matters more than most investors are pricing in. ServiceNow’s federal and Middle East deal pipeline took a direct hit from the Iran war, so a ceasefire or de-escalation would remove a real headwind.
Finally, the IGV chart is the cleanest sector tell. If software exchange-traded funds (ETFs) can hold current levels and start climbing back toward the 200-day moving average, then dip buyers are winning. If IGV breaks lower from here, Trump’s Feb. 10 trade may need a long time to work out.
For now, the recent Trump disclosure is doing exactly what high-profile trade disclosures tend to do. It’s generating headlines, moving NOW in overnight trading, and forcing every investor with software exposure to ask whether they’re holding a bargain or a value trap. The answer probably depends on whether agentic AI ends up being a tailwind for the incumbents — or the thing that finally breaks them.
On the date of publication, Oscar Cierpial did not have (either directly or indirectly) positions in any of the securities mentioned in this article. All information and data in this article is solely for informational purposes. This article was originally published on Barchart.com
