A director of the Chelsea Football Club with Canadian ties has been added to the United Kingdom’s list of individuals sanctioned in connection with Russia’s invasion of Ukraine.

Eugene Tenenbaum, described as one of Russian businessman and Chelsea owner Roman Abramovich’s “closest associates” on the team website, was added to the U.K.’s list on Thursday, along with David Davidovich, another long-time Abramovich associate.

U.K. Foreign Secretary Liz Truss said the government was freezing assets connected with the pair estimated to total up to £10 billion ($16.4 billion), making it the largest asset freeze action in U.K. history.

“We are tightening the ratchet on Putin’s war machine and targeting the circle of people closest to the Kremlin. We will keep going with sanctions until Putin fails in Ukraine. Nothing and no one is off the table,” Truss said in a statement.

The U.K. government said Tenenbaum was subject to an asset freeze and that Davidovich was subject to a travel ban and asset freeze.