I'm a day late, but here's Herblock from 1952.

[JHB]

2. He passed in 2001, and he did take a swipe at Trump

This is from 1999, when Trump was dabbling with a candidacy in Ross Perot's Reform Party.

According to editorial cartoonist Herb Block, better known as Herblock, the stupidest tea party was when, in October 1999, presidential candidate Patrick Buchanan switched from the Republican Party to the Reform Party, creating divisiveness within the emerging third party as his political platform differed markedly from that of founder Ross Perot. In the meantime, real estate magnate Donald Trump had formally established his Reform Party candidacy. Trump was favored as the “Stop Buchanan” candidate, but in February 2000, he withdrew from the race. In August 2000, Patrick Buchanan accepted the presidential nomination from one wing of a decidedly split Reform Party. For Herb Block, the situation evoked one of Sir John Tenniel’s famous illustrations for Lewis Carroll’s “Alice’s Adventures in Wonderland.”

https://downtherabbitholemag.wordpress.com/2015/04/24/political-cartoons/