Trump Media & Technology Group Corp. (Nasdaq: DJT), the owner of Truth Social, closed at $6.47 on October 20, 2026, a day after a record-low close of $6.43. Long/short fund manager Sean Westropp of Deep Sail Capital says the stock still has 100% downside, pointing to Truth Social traffic that fell more than 30% in a year. The next tests are the pending all-stock merger with fusion company TAE Technologies, which has a December 18, 2026 outside date, and the bitcoin-heavy balance sheet.
This is journalism and commentary, not investment advice. We hold no position unless stated.
Key facts
- Ticker and exchange: Trump Media & Technology Group Corp., DJT, Nasdaq (also listed on NYSE Texas).
- Situation type: contrarian short on a low-revenue media company in the middle of a transforming merger.
- The call: Deep Sail Capital (@DeepSailCapital) posted on October 14, 2026 that DJT has 100% downside, at a $7.22 prior close.
- Price: $6.47 at the October 20, 2026 close, down about 51% from $13.24 on December 31, 2025.
- Traffic: Truth Social averaged about 260,000 daily users in September 2026, down from a 420,000 peak in June 2025, per Similarweb data reported by The Washington Post.
- Catalyst: the TAE merger vote, which still needs an effective S-4 and a meeting date, before the December 18, 2026 outside date.
- Main risk to the short: about $893 million of net financial assets as of June 30, 2026, mostly bitcoin.
Is Trump Media stock a good bet right now?
The bear case is the operating business. Trump Media reported second-quarter 2026 revenue of $1.67 million and a net loss of $238.1 million, per its Q2 2026 10-Q.
The bull case is the balance sheet and the merger. On the Q2 call, management cited $1.9 billion of gross financial assets and about $893 million net of debt. With roughly 277 million shares, that is about $3.20 a share by our math, before any bitcoin moves since June 30.
Why are investors bearish on Trump Media?
- Users are leaving. The Washington Post reported the 30% traffic drop on October 14, 2026.
- Revenue is tiny. Second-quarter revenue of $1.67 million compares with $35.9 million of general and administrative expense.
- The merger doubles the share count. The S-4 asks holders to raise authorized shares from 999 million to 1.998 billion, and TAE holders would own about half the combined company.
- Bitcoin cuts both ways. Losses on digital assets were $116.7 million in the second quarter alone.
Who's making this call and why?
Sean Westropp runs Deep Sail Capital, a long/short fund, and posts as @DeepSailCapital. Quoting the traffic report on October 14, 2026, he wrote: "$DJT Downside still 100% from here."
It is a long-running short. On June 24, 2026 he called Trump Media a "$2 Billion Melting Ice Cube." On August 31 he added that DJT had "a long way to go to zero over the next few years."
Track record. In our tracking, Deep Sail Capital is 13-12 (a .520 win rate) on 25 calls scored at 180 days against the S&P 500, with an average edge of +8.9 percentage points, ranked 6th on the career table. Its shorts are 9-4, though its last 10 scored calls went 2-8. The June DJT short trailed the S&P 500 by 13.6 points at 90 days, but as of October 20 it is ahead by about 22.6 points, a provisional figure that does not count yet. See the scoreboard.
A supporter on dilution. Michael Listman, a self-described RIA and options premium seller, argued on October 15 that the TAE deal "will massively dilute the book value of the shares." He also questioned how Trump Media's revenue could fund TAE until fusion power is profitable.
Who disagrees?
- The deal math. RaiderPete, a small trader account, replied that Listman's post "is inaccurate on the structure and misleading on the valuation math." His point: the exchange ratio is fixed for a roughly 50/50 split, and new TAE shares face a six-month lockup.
- Worth the price. Spearfishing Capital, a self-described $300 million family office, noted that existing holders are "ceding half of their equity ownership and a $300m cash giveaway," then concluded the deal is probably worth it.
- The company. A Trump Media spokesperson dismissed the traffic figures and accused The Washington Post of bias, as reported by NDTV.
- Asset backing. Net financial assets of about $893 million cover roughly half of the $1.8 billion market cap that Forbes cited on October 20.
What are the key facts to verify?
- The Q2 2026 10-Q for revenue, losses and the 9,477 bitcoin held on June 30, 2026.
- The S-4 for the share issuance, vote thresholds and the blank meeting date.
- TAE's September 30 release on the 50/50 ownership split.
- Similarweb's traffic estimates, which the company disputes.
What would prove it right or wrong?
Right: traffic keeps falling, the merger closes and the combined company burns cash, bitcoin weakens, or holders reject the deal and the December 18, 2026 outside date passes with no plan.
Wrong: the stock rerates on the fusion story after closing, bitcoin rallies and lifts net assets per share, or Trump Media trades back toward its $893 million of net financial assets with a premium for TAE.
This is journalism and commentary, not investment advice. We hold no position unless stated.