"Wish the moon wasn't the only thing casting a shadow across the country," Blankfein tweeted, without mentioning Trump by name. "We got through one, we'll get through the other."
The afternoon tweet came less than an hour after the once-in-a-century solar eclipse passed over the country, and many Twitter users poked fun at pictures of Trump attempting to view the eclipse with the naked eye. NASA and other scientific authorities have warned that watching the eclipse without proper glasses could damage eyesight.
A Goldman Sachs spokesperson told CNBC that Blankfein's "tweet speaks for itself."
The White House did not immediately respond to a request for comment.
Of 13 tweets from his verified account, including Monday's, Blankfein has appeared to troll the president at least four times. The bank executive previously called out Trump's decision to withdraw from the Paris climate-change accord and appeared to jab at the president over a themed "infrastructure week" that ended up focusing on former FBI Director James Comey's testimony.
In a prime-time address Monday night, Trump laid out his strategy for the war in Afghanistan.
The speech came after a tumultuous week for the White House in which key advisory councils of top business leaders disbanded, and Steve Bannon left his role as chief strategist.
On Aug. 14, Blankfein cited President Abraham Lincoln's remark that "a house divided against itself cannot stand" in a tweet referencing violence during a white supremacist march earlier this month in Charlottesville, Virginia. The Goldman executive then added to his tweet, "Isolate those who try to separate us. No equivalence w/ those who bring us together."