Dave Portnoy Doubles Down on XRP with $1M Buy Amid Market Bloodbath

Barstool Sports founder Dave Portnoy made headlines this week by purchasing over $2 million in cryptocurrency during Monday's market downturn, including a $1 million position in XRP. The high-profile investor's aggressive re-entry into the market drew immediate attention from both crypto enthusiasts and skeptics, particularly given his well-documented history of poorly-timed crypto trades.

The "Blood in the Streets" Trade

On November 17, 2025, Portnoy executed rapid-fire purchases totaling $2 million across three major cryptocurrencies: $1 million in XRP (split between two $500,000 purchases at 6:36 PM and 6:38 PM), $750,000 in Bitcoin at 6:37 PM, and $400,000 in Ethereum. Announcing his move on X to his 3.7 million followers, Portnoy invoked the classic contrarian investing principle: "When there's blood in the streets, I'm like a Great White Shark."

The timing aligned with significant market weakness. XRP was trading at $2.14 after dropping 10.3% in the past week, Bitcoin sat at $90,919 (down 12% over the same period), while Ethereum had fallen to $3,038 (down 11.77%). On monthly charts, the losses deepened further, with Bitcoin down 18.5%, Ethereum down 25.5%, and XRP down 13.14%.

Eric Trump publicly praised the move on X, calling it a "smart trade," adding a notable endorsement from the crypto-friendly Trump family.

Why XRP? Portnoy's Candid Investment Philosophy

Portnoy has been remarkably transparent about his investment rationale for XRP—or lack thereof. In a May interview, Portnoy explained his interest in XRP is mainly due to "good FOMO," likening the token's upside potential to Bitcoin's early days. He has openly admitted he doesn't rely on XRP's fundamentals but sees it as one of the few tokens that still carries underdog appeal.

This purchase represents Portnoy's latest chapter in a tumultuous relationship with XRP. In July 2025, Portnoy regretted panic-selling roughly $3 million worth of XRP at $2.40 after misinterpreting a friend's warning text, only to watch helplessly as XRP surged to $3.65 shortly after. He publicly stated the missed rally made him "sick" and that he "wanted to cry."

In December 2024, Portnoy disclosed holdings of $1.5 million in Bitcoin and $1.3 million in XRP. With this latest $2 million purchase, his total crypto portfolio now exceeds $4 million—assuming he hasn't sold any previous holdings.

Market Context: Retail Capitulation Signals

The broader market conditions that prompted Portnoy's purchase reveal important dynamics about investor sentiment. According to blockchain analytics firm Santiment, the crypto market showed signs of retail trader capitulation, particularly among holders of Bitcoin, XRP, and Ethereum, the crypto market showed signs of retail trader capitulation, particularly among holders of Bitcoin, XRP, and Ethereum. Santiment has historically observed that retail capitulation often precedes market recovery phases, as fearful retail investors exit positions that stronger hands then accumulate.

Market analyst Satraj Bambra, CEO of Rails and Managing Partner at Round13, explained the persistent weakness: "October's liquidation event was a major catalyst for Bitcoin's dip below $90K. It created a liquidity vacuum, and when markets are already weak, they don't need a fundamental reason to puke; they just need an opening."

The Monday market wipeout erased all of Bitcoin's gains in 2025, creating the type of panic selling environment that contrarian investors like Portnoy typically view as buying opportunities.

XRP-Specific Analysis: Mixed Signals for Ripple's Token

Recent Price Action and Market Structure

XRP has entered bear market territory with a 13.88% monthly decline in November—the largest monthly drop since February 2025—and has formed a confirmed death cross pattern on daily charts (where the 50-day moving average crosses below the 200-day moving average). The cryptocurrency is currently trading around $2.14, significantly below its July 2025 high of $3.65.

However, some technical analysts see potential support forming. Market observers note that XRP has been in a re-accumulation phase between $1.99 support and $3.30 resistance since early 2025. The token is holding above key support near $2.15–$2.20, which some analysts view as a critical demand zone.

ETF Developments: Promise and Disappointment

Canary Capital's spot XRP ETF attracted $268 million at launch—the largest crypto ETF debut of 2025. This represented a significant milestone for XRP's institutional legitimacy. However, the ETF launch failed to translate into sustained price momentum.

Despite the initial ETF inflows, XRP dropped 12% weekly, with only 58.5% of holders now in profit—the lowest percentage since 2024. This "sell the news" behavior suggests that traders who anticipated the ETF approval had already positioned themselves, leaving no additional buying pressure once the news became official.

Whale Activity: Divergent Behavior

On-chain data reveals complex dynamics among large holders. Between October 28 and 30, mid-sized whale balances grew from 6.28 billion to 6.31 billion XRP, adding approximately 30 million tokens worth roughly $74 million. This suggested early stabilization among sophisticated investors.

However, whales also sold approximately 70 million XRP over two days in late October, indicating that smart money remained cautious. This creates a mixed picture: some large holders are accumulating during weakness, while others are taking profits.

Meanwhile, long-term holders have accelerated selling, with the Hodler Net Position Change metric showing outflows deepening from -3.28 million XRP on October 19 to -90.14 million XRP by October 30—a 2,647% increase in net outflows over just two weeks.

Potential Catalysts for XRP Price

Several factors could influence XRP's trajectory in the coming months:

Positive Factors:

• Multiple spot XRP ETF filings await SEC decisions, including applications from Grayscale, Bitwise, Canary, WisdomTree, and CoinShares
• Ripple's continued expansion of RippleNet partnerships for cross-border payments
• Recent XRP Ledger upgrades including Version 2.5.0 with batch transactions, token escrow, and permissioned DEX features
• Resolution of Ripple's legal challenges with the SEC

Bearish Headwinds:

• Crypto analyst Master predicts extreme capitulation to $1.00, representing a potential 54% decline from current levels
• Death cross technical pattern typically signals extended bearish momentum
• XRP has broken below the critical $2.20 support level
• Continued liquidation pressures and weak overall crypto market sentiment

Price Predictions: Wide Divergence

Expert forecasts for XRP vary dramatically, reflecting the uncertainty in current market conditions:

Bearish Scenarios:

• Technical analysis suggests potential decline to $1.25 (representing a 50% drop from recent highs), which would mark the yearly minimum and 100% Fibonacci extension from July peaks to October lows
• Intermediate support exists at the $2.00 psychological level and $1.90 June lows

Neutral Projections:

• Changelly projects a $2.11–$2.45 range through December 2025

Bullish Scenarios:

• Optimistic forecasts cite $5.05 by year-end driven by ETF approvals and regulatory clarity
• Standard Chartered analyst Geoffrey Kendrick projects 73% annual growth over three years
• Some bulls target $10–$37 for the current market cycle

Reality Check: The dramatic divergence between bearish technical projections ($1.00–$1.25) and optimistic fundamental forecasts ($5.05+) reflects extreme market uncertainty. Price predictions in cryptocurrency markets have historically proven unreliable, particularly during periods of high volatility.

The Portnoy Track Record: A Cautionary Tale

Portnoy's crypto investment history serves as a reminder of the risks inherent in emotional, momentum-driven trading. His first serious crypto exposure came in August 2020 when the Winklevoss twins visited his house to explain Bitcoin. He famously declared he was "up $100K in Bitcoin" shortly after buying, but his enthusiasm proved short-lived.

The crypto community has had a mixed reaction to this latest purchase, with many traders sharing memes and jokes about Portnoy's historically poor timing. His tendency to buy near peaks and sell near bottoms has become something of a running joke in crypto circles—some traders even use his moves as contrarian indicators.

However, defenders of Portnoy's strategy point out that his "blood in the streets" approach aligns with classic value investing principles popularized by Baron Rothschild and later Warren Buffett. Whether this particular instance represents savvy bottom-fishing or another mistimed entry remains to be seen.

Bottom Line: What Does This Mean for Investors?

Dave Portnoy's $1 million XRP purchase represents a high-profile bet that the current market downturn presents a buying opportunity rather than the beginning of extended weakness. His timing coincides with classic capitulation signals—retail selling, extreme fear, and sharp price declines—that have historically marked market bottoms.

However, several important caveats apply:

1. Portnoy's track record is mixed at best. His history of panic selling and poorly-timed entries suggests his moves should not be viewed as expert market timing.
2. Technical indicators remain bearish. The death cross pattern and breaks below key support levels suggest further downside risk remains possible.
3. XRP faces unique challenges. While ETF launches provide legitimacy, the "sell the news" behavior and mixed whale activity indicate uncertainty about near-term catalysts.
4. Market conditions remain fragile. The October liquidation event created structural weakness that may take time to resolve.

For investors considering following Portnoy's lead, the key question is whether current prices represent value or merely a falling knife. Those who share his contrarian conviction should be prepared for potential further declines and extended recovery periods. Those skeptical of his timing may prefer to wait for clearer technical confirmation of a trend reversal before committing capital.

As always in cryptocurrency markets, position sizing and risk management remain paramount. Even if Portnoy's "blood in the streets" thesis proves correct, the path to recovery is rarely smooth or predictable.

DISCLAIMER: This newsletter is for informational purposes only and does not constitute investment advice, advertising, or a recommendation to buy, sell, or hold any securities. This content is not sponsored by or affiliated with any of the mentioned entities. Investments in cryptocurrencies or other financial assets carry significant risks, including the potential for total loss, extreme volatility, and regulatory uncertainty. Past performance is not indicative of future results. Always consult a qualified financial professional and conduct thorough research before making any investment decisions.

Sources & References

Primary Sources:

1. The Crypto Basic - Eric Trump Endorses Dave Portnoy's $1M XRP Purchase
   Coverage of Portnoy's November 17, 2025 cryptocurrency purchases and market reaction
2. Crypto Briefing - Dave Portnoy Acquires $1 Million in XRP After Missing Previous Rally
   Analysis of Portnoy's trading history and latest market re-entry
3. U.Today - Portnoy Announces Enormous XRP Purchase
   Historical context on Portnoy's cryptocurrency investment timeline

Market Analysis & Data:

4. TradingView News via Coinpedia - Dave Portnoy Buys Bitcoin, Ethereum, and XRP Amid Signs of Potential Crypto Rebound
   Retail capitulation signals and Santiment market analysis
5. Benzinga - Dave Portnoy Says He's Like A 'Great White Shark' When There's Blood In The Streets, Reveals $2 Million Worth Of Crypto Purchases
   Portfolio holdings updates and transaction details
6. CCN - Dave Portnoy's $2M Crypto Buy: Why Traders Are Worried
   Community reaction and market sentiment analysis

XRP Technical & Fundamental Analysis:

7. Finance Magnates - How Low Can XRP Go? Expert Predicts Potential $1 Capitulation
   Technical analysis, death cross patterns, and bearish price predictions
8. BeInCrypto - XRP Price Outlook for November 2025
   Whale accumulation data and on-chain metrics analysis
9. Brave New Coin - XRP Price Analysis: Capitulation May Spark Bullish Run
   Re-accumulation phase analysis and technical resistance levels
10. CoinDCX - XRP Price Prediction Weekly Analysis
    Support zone identification and near-term price forecasts
11. CoinMarketCap - Latest XRP News and Updates
    ETF performance data, XRP Ledger upgrades, and market capitalization changes
12. Crypto.News - XRP Price Analysis: Retail Capitulation Could Mark Rebound Zone
    Whale selling activity and retail sentiment indicators
13. Ventureburn - XRP Price Prediction 2025-2030
    Long-term forecasts, ETF filing status, and institutional adoption projections

Historical Context:

14. Crypto Briefing - Dave Portnoy Regrets Selling XRP Before 50% Rally
    July 2025 sale details and subsequent price movement
15. Crypto Briefing - Eric Trump Responds to Portnoy's Crypto Purchases
    Trump family crypto advocacy and market commentary

All hyperlinks verified as of November 19, 2025. Market data and prices are subject to change. Readers are encouraged to verify current information independently.