The United States president and Mr Macron gazed into each others eyes as they both opted for a firm grip, complete with white knuckles and grimaces.
But it was the French president who appeared to keep the handshake going as Mr Trump attempted to pull away.
France 24’s White House pool reporter Philip Crowther, who was on the scene, said both leaders’ jaws clenched as a result.
He said: "The two presidents, each wearing dark suits and blue ties (Trump's was thick and royal blue; Macron's was skinny and navy) sat in antique cream-upholstered arm chairs, with two American and French flags behind them.
Donald Trump and Emmanuel Macron "clenched jaws" during an extended handshake
Each president gripped the other's hand with considerable intensity, their knuckles turning white
"They shook hands for an extended period of time. Each president gripped the other's hand with considerable intensity, their knuckles turning white and their jaws clenching and faces tightening."
It is not the first time the Republican billionaire has caught the attention of the media with his handshake.
His style came under scrutiny after an aggressive meeting with the Japanese and Canadia leaders.
He was analysed after he held on to the Japanese Prime Minister, Shinzo Abe’s hand for 19 seconds.
Donald Trump in Brussels
Thu, May 25, 2017
Donald Trump has arrived in Brussels for talks with European leaders at the European Council
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Donald Trump talks with President of the European Council, Donald Tusk
Donald Trump then patted the leaders hand before Mr Abe was left reeling from the aggressive encounter.
However the billionaire welcomed Canadian Prime Minister, Justin Trudeau, as the pair both greeted strongly in a heated introduction.