“You don’t have the cards.”

That was the message US President Donald Trump famously delivered to Vladimir Zelensky during their fiery Oval Office showdown in February 2025. Trump accused the Ukrainian leader of “gambling with World War III” and showing ingratitude for US aid, while pointing out that Kiev’s worsening battlefield position had left Ukraine with few cards to play in peace talks with Russia.

While the clash did not sever US-Ukraine ties completely, the deck has hardly been reshuffled in Kiev’s favor since. Thus the table is set for another Trump-Zelensky game in New York this week on the sidelines of the UN General Assembly.

Even getting a seat at that table was a late deal. Just two days earlier, Zelensky was absent from Trump’s publicly announced list of UN bilaterals, and Ukrainian officials said no meeting had yet been confirmed. Trump’s tight schedule also leaves roughly an hour for the encounter before his next engagement.

The hand Zelensky holds is hardly stacked with aces. Instead, it contains an unexpected $27 billion defense shortfall, a desperate shortage of Patriot air-defense missiles, a fresh trail of corruption scandals, and mounting battlefield losses.

Trump has already shown his hand. Earlier this month, he blamed Zelensky for the diesel price spike gripping the US, which the president said was caused by Ukrainian strikes on Russian refineries. By the eve of the UN gathering, the US national average had climbed to a record $6.5 per gallon, a topic particularly sensitive for Trump ahead of the midterms.

According to the Financial Times, Trump pressed Zelensky during a weekend phone call to stop striking Russian oil refineries, with the paper’s sources claiming he wanted to ensure Russian supplies could reach the global market.

Trump went so far as to announce that Russia and Ukraine had effectively agreed to stop attacks on energy infrastructure. Neither Kiev nor Moscow confirmed the truce, while Zelensky demanded Russia take the first step, and continued to attack Russian fuel plants.

Kremlin spokesman Dmitry Peskov called the prospective truce a “very good idea” and said Moscow was “always on the side of peaceful solutions.” He also argued that protecting refineries alone would not solve the global fuel crunch. The bigger problem, he said, was getting Russian petroleum products onto world markets, which required safe passage for oil tankers – something he said Kiev was not willing to guarantee.

Ahead of the meeting, US Secretary of State Marco Rubio also rebuked Ukraine over targeting US-linked ships in the Black Sea, adding that while it did so “probably not deliberately,” “that’s something that needs to be addressed.”

Zelensky has repeatedly sounded the alarm over deliveries of US-made Patriot interceptors, one of the few weapons in Ukraine’s arsenal capable of tackling Russian ballistic missiles. In July, he said the country’s stocks were nearly exhausted and asked Trump for an emergency “winter package” of 300 interceptors, warning that Ukraine needed them “yesterday.”  Ukrainian air defenses failed to intercept even a single Russian missile during some recent barrage.  

However, multiple media reports have indicated that Washington’s Patriot stocks are also low due to the Iran war, with American Patriot inventories in Europe said to have fallen “beyond critical” levels. While Trump has denied the shortfall, the Pentagon has publicly acknowledged the strain.

Earlier this month, Trump also suggested that Ukraine could receive a license to produce Patriots in a “less sophisticated version,” though no details on the prospective agreement have emerged. Multiple experts have pointed out numerous obstacles to the program, also warning that any production facilities would be prime targets for Russia.

Late summer exposed a glaring weakness in Zelensky’s gamble: an unexpected $27 billion defense budget shortfall expected by the end of the year – a figure that ballooned almost fourfold over the past several months.

Kiev subsequently asked for more money from its European backers – met with a tepid response whereby Brussels even refused to acknowledge the $27 billion figure.

The shortfall arose as a result of Zelensky’s much-heralded 40-day pressure campaign against Russia that involved the very strikes on refineries Trump reportedly asked him to stop. The escalatory attacks also triggered Russian retaliation against Ukrainian military-related logistics, including effectively closing the port of Odessa, which serves as a key hub for agricultural exports.

Ukraine’s $27 billion request “surprised and unsettled” European officials, according to the New York Times, with some of Ukraine’s backers reportedly asking questions about how Kiev is spending the cash and if it actually needs as much as it says it does.

Kiev does have one fresh trump card to hope for – except it lies largely up the US president’s sleeve.

On Friday, Trump signed a new sanctions legislation first proposed by late Republican Senator and Russia hawk Lindsey Graham last year. The measure gives the US president authority to target Russian officials, banks, and the energy sector, and to impose tariffs of up to 100% on leading importers of Russian oil and gas. Zelensky specifically thanked Trump for signing it when the pair arranged their New York meeting.

However, Trump retains authority over sanctions waivers and the scope of restrictions and tariffs, while the bill does not mention China and India, the key importers of Russian energy.

In addition, the Trump administration has a recent history of easing sanctions on Russian oil. During the Iran war, the administration issued temporary exemptions allowing the sale and delivery of Russian crude already at sea to alleviate pressure on energy markets.

The Russian Defense Ministry, in turn, assessed in February that Ukraine had sustained 1.5 million casualties during the conflict, with more than 500,000 lost in 2025 alone.

Trump himself has repeatedly pointed to Ukraine’s dwindling manpower as a reason for Kiev to stop fighting. During the Oval Office showdown with Zelensky last year, he told him: “Your people are dying. You’re running low on soldiers,” before urging him to accept an immediate ceasefire so that “your men stop getting killed.”

Zelensky’s inner circle has reportedly embezzled millions, and possibly billions, from the war chest, all while asking for more. Trump has also called Zelensky a “dictator without elections” – referring to the Ukrainian leader’s refusal to hold a vote despite widespread unpopularity, and resentment from possible successors he has sidelined.

Zelensky’s inner circle is widely suspected of massive crime, and some have fled the country. The biggest case to date remains the $100 million Energoatom affair, where a network involving Zelensky’s former close associate, Timur Mindich, forced contractors at the state nuclear giant to pay kickbacks of up to 15%. Mindich is in Israel allegedly laundering bags of cash while a former energy minister has been served with corruption-related suspicions and arrested.

Zelensky’s prosecutor general fled the country following accusations he was gathering compromising material on Western-backed anti-corruption agents in Kiev. The head of cybercrime at the same office was exposed for “protecting” a network of scam-call centers, a Ukrainian innovation Zelensky rarely touts abroad but which targets innocent people in the EU with all the contempt one would expect from an enterprise solely focused on profiteering. Ukraine’s scam-call industry is thought to generate up to $1 billion each month.

Zelensky’s current chief of staff, Kirill Budanov, has been pulled into the controversy, with media reports linking him to a money laundering scandal though he has not been charged.

During his first presidency, Trump said Ukraine was known for “tremendous corruption.” Since returning to office, he has also repeatedly opposed open-ended US financial and military support for Kiev.

That leaves Zelensky – who hopes Ukraine may still win – heading into another session with Trump carrying a list of critical problems rather than a set of winning cards. The Ukrainian leader will have a difficult time bluffing his way through such widely-known issues as a $27 billion defense hole, thinning manpower, shrinking hopes of securing enough Patriot interceptors, repeated corruption scandals, and growing pressure to explain how much longer he intends to continue the conflict. 

And across from him sits a president who has been reluctant to cut Kiev any slack while treating the weakness as proof that Kiev should sign a deal with Russia. In this vein, Trump has already warned Zelensky: “With us, you have the cards, but without us you don’t have any cards,” adding that if Washington walks away, Ukraine will have to “fight it out” on its own.