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Trump Media Faces $1 Billion Payment Risk; Bitcoin Sale Could Be on the Table

Trump Media reported that it could face a payment of about $1 billion if bondholders exercise their right to cash repayment on November 30, and may have to sell Bitcoin if other financing options prove insufficient.

According to a November 2 securities filing cited by CoinDesk, convertible bondholders of the parent company of Truth Social may demand cash repayment at the end of the month. The approximately $1 billion amount would come into play if all bondholders exercised this right.

The company said it may need to sell Bitcoin or other digital assets to meet the repayments if refinancing or other measures are insufficient. This makes November 30 a critical date for investors, while the potential sale’s size will depend on repayment demands and the financing that can be secured.

Bitcoin moved to exchange from collateral-linked addresses

Earlier, the transfer of 4,259 BTC associated with Trump Media to Crypto.com drew attention. According to Arkham labels, the coins were moved from addresses associated with assets pledged as collateral for the company’s convertible bonds due in 2028.

In two transactions, approximately 2,140 BTC and 2,119 BTC were sent to the same destination address. The dollar values shown on the transaction screen in the source indicate a total of $343.67 million.

The company’s second-quarter filing stated that 4,260.73 BTC had been pledged as collateral for the bonds as of June 30, and that the agreement restricted the withdrawal or distribution of these coins. While the address labels are consistent with this collateral arrangement, the purpose of the latest transfer has yet to be clarified.

Crypto.com is also a custody partner

Crypto.com has been one of Trump Media’s custody partners since the company launched its Bitcoin treasury strategy. In May 2026, the company said a transfer of approximately 2,650 BTC was not a sale, but was made as part of its general trading strategy. It also cited custody management as the reason for the 2,628 BTC transferred to the same platform in August.

There is no confirmation that the latest move was a sale. However, the company’s own filing’s conditional warning about selling digital assets shows why repayment demands at the end of the month are being closely watched.

Not investment advice.

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