Donald Trump

when

President Donald Trump

Markets are bracing for a potentially market-moving U.S. Supreme Court <a href="https://www.supremecourt.gov/search.aspx?filename=%2Fdocket%2Fdocketfiles%2Fhtml%2Fpublic%2F24-1287.html&amp;utm" rel="noopener noreferrer nofollow">ruling</a>&nbsp;this Friday on the legality of President Donald Trump’s sweeping tariffs.
With traders warning of chaos and prediction markets heavily skewed toward a loss for Trump,&nbsp;<a href="https://www.thestreet.com/crypto/trading/wall-street-legend-asks-shareholders-to-approve-huge-equity-expansion" rel="noopener noreferrer nofollow">Tom Lee</a>, the veteran Wall Street strategist behind Fundstrat,&nbsp;is floating the opposite idea.
<a href="https://www.thestreet.com/crypto/markets/billionaire-investor-says-theres-no-real-exit-from-money-printing" rel="noopener noreferrer nofollow">Related: Billionaire investor says there’s no real exit from money printing</a>
<h2 id="trump-tariffs-and-supreme-court-decision">Trump tariffs and Supreme Court decision</h2>
The legal battle centers on tariffs imposed by Trump in early 2025 under the International Emergency Economic Powers Act, a 1977 law typically used for sanctions during national emergencies.
Trump used the statute to justify broad “<a href="https://www.thestreet.com/crypto/policy/polymarket-traders-bet-on-tariff-targets-as-trump-declares-liberation-day-" rel="noopener noreferrer nofollow">Liberation Day</a>” tariffs of 10% to 50% on global imports, along with targeted duties on China, Canada and Mexico tied to fentanyl trafficking concerns.
The administration argued persistent trade deficits and national security risks qualified as an emergency.
Lower <a href="https://www.reuters.com/world/us/trump-takes-tariffs-fight-us-supreme-court-2025-09-04" rel="noopener noreferrer nofollow">courts disagreed</a>.
Both the U.S. Court of International Trade and a federal appeals court ruled that Trump exceeded his authority, finding that Congress, not the president, holds primary power over tariffs.
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 <img src="https://www.thestreet.com/.image/c_fit%2Ch_800%2Cw_1200/MjIwNDE1NDU0OTYxNzM4ODIy/gettyimages-2194921722.jpg" height="800" width="1200">
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 U.S. President Donald Trump gestures to U.S. Supreme Court Chief Justice John Roberts after he was sworn in during inauguration ceremonies on January 20, 2025 in Washington, DC.
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The Supreme Court <a href="https://www.nytimes.com/live/2025/11/05/us/trump-tariffs-supreme-court" rel="noopener noreferrer nofollow">heard arguments</a> in November, where both conservative and liberal justices expressed skepticism. The court has signaled it may release rulings on Jan. 9, though it doesn't disclose them in advance.
If the tariffs are struck down, it would have massive financial repercussions.
As per a Reuters report, more than $133.5 billion in tariffs could be <a href="https://www.reuters.com/world/us/us-tariffs-that-are-risk-court-ordered-refunds-exceed-1335-billion-2026-01-06" rel="noopener noreferrer nofollow">subject to refunds</a>, raising questions about timing, fiscal impact and replacement policies.
<h3 id="popular-on-thestreet-roundtable">Popular on TheStreet Roundtable:</h3>
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 <li><a href="https://www.thestreet.com/crypto/markets/venezuela-bitcoin-reserve-michael-saylor-microstrategy" rel="noopener noreferrer nofollow">Venezuela could hold as much Bitcoin as Michael Saylor’s MicroStrategy</a></li>
</ul>
<h2 id="breaking-down-the-market-reaction-warning">Breaking down the market reaction warning</h2>
The uncertainty has fueled sharp warnings from sections of Crypto Twitter.
Trader Wimar.X went <a href="https://x.com/DefiWimar/status/2008672561991651746?s=20" rel="noopener noreferrer nofollow">viral this week</a>, calling Friday “the worst day of 2026” and arguing that a negative ruling could trigger simultaneous sell-offs across stocks, bonds and crypto.
He pointed to Trump’s <a href="https://www.thehindu.com/news/international/us-will-receive-600-billion-in-tariffs-trump/article70475701.ece" rel="noopener noreferrer nofollow">repeated claims</a> that tariffs generated roughly $600 billion in revenue. If courts rule the tariffs illegal, traders would immediately debate how much money must be refunded and how quickly.
“That’s not clarity. That’s chaos,” Wimar wrote, warning of refund disputes, emergency tariff replacements and retaliation risk, all hitting markets at once.
Prediction markets also reflect those fears.
Traders on&nbsp;<a href="https://polymarket.com/event/will-the-supreme-court-rule-in-favor-of-trumps-tariffs" rel="noopener noreferrer nofollow">Polymarket</a>,&nbsp;the crypto-based prediction market,&nbsp;think there is roughly a 21% chance that the Supreme Court rules in favor of Trump’s tariffs, implying markets largely expect a loss.
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 Data from Polymarket at the time of writing.
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Critics of the bearish view <a href="https://www.reuters.com/world/us/trump-supreme-court-tariff-defeat-would-add-trade-uncertainty-2025-11-06" rel="noopener noreferrer nofollow">argue </a>that even if tariffs are invalidated, refunds would be slow, contested and handled through agencies and courts, not instant market shocks.
<h2 id="wall-street-veteran-s-contrarian-signal">Wall Street veteran’s contrarian signal</h2>
Enters <a href="https://www.thestreet.com/crypto/markets/legendary-analyst-reveals-2026-stock-nice-list" rel="noopener noreferrer nofollow">Tom Lee</a>, the co-founder of Fundstrat Global Advisors and the chairman of the <a href="https://thestreet.com/crypto/ethereum" rel="noopener noreferrer nofollow">Ethereum</a> treasury company, <a href="https://www.thestreet.com/crypto/trading/wall-street-stock-ceo" rel="noopener noreferrer nofollow">Bitmine Immersion Technologies</a> (NYSE: BMNR).
Quoting the viral warning post on 7th Jan., Lee <a href="https://x.com/fundstrat/status/2008765757912465716?s=20" rel="noopener noreferrer nofollow">responded</a>:
<blockquote>
 “ummm… perhaps this could be a contrarian signal.”
</blockquote>
Lee has long argued that markets tend to bottom when fear is widespread and heavily priced in.
He has previously <a href="https://fortune.com/2026/01/05/wall-street-permabull-tom-lee-2026-outlook-labor-shortage-frozen-food/" rel="noopener noreferrer nofollow">argued</a> that&nbsp;tariffs and other geopolitical tensions have collectively “made investors very nervous about… investing in full risk."
<blockquote>
 “Markets climb a wall of worry,” he said.
</blockquote>
Markets sometimes keep rising even when investors are anxious. Market peaks don't occur when traders are&nbsp;pessimistic; instead, peaks occur when traders are in a state of euphoria and good news stops pushing prices higher.&nbsp;
Currently, skepticism remains high, which the Wall Street veteran views as a "contrarian buy signal."
What it means is that since many traders are still skeptical right now, he believes this pessimism itself is a sign that the market may have more room to climb, making it a potential buying opportunity.
Lee's logic suggests that with traders already prepared for a potentially negative ruling, the actual outcome may prove less disruptive than expected.
At the time of writing, crypto markets were trading lower, with risk assets under pressure ahead of the looming decision.
Bitcoin <a href="https://www.coingecko.com/" rel="noopener noreferrer nofollow">traded </a>near $91,500, down about 3% over 24 hours, while Ether hovered around $3,190, down roughly 3.2%.
Solana changed hands near $137, also lower on the day.
The global crypto market cap stood around $3.23 trillion, with traders waiting to see whether Friday delivers the volatility shock many fear or the contrarian signal Lee is hinting at.
<a href="https://www.thestreet.com/crypto/trading/wall-street-legend-asks-shareholders-to-approve-huge-equity-expansion" rel="noopener noreferrer nofollow">Related: Wall Street legend asks shareholders to approve huge equity expansion</a>

Wall Street veteran drops major hint ahead of Trump’s Friday tariff ruling

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