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According to a BBC ariticle, Trump has made comments like:
Jeremy Corbyn would be "so bad" as prime minister
Of Boris Johnson:
"[He's] the exact right guy for the times"
Is it usual for a US President to specifically endorse a UK Prime Minister during a General Election campaign?
According to VOA, it hasn't been this blatant before, at least as actual elections go:
During his time in office, Trump's predecessor, Barack Obama, weighed in on Brexit in 2016, provoking fury from the referendum's supporters for saying London would be at the "back of the queue" for a trade deal if it left the European Union, noted Ben Riley-Smith, U.S. editor of the Daily Telegraph.
"And the consensus of that was it backfired," said Joe Lockhart, who was White House press secretary under U.S. President Bill Clinton. [...]
The virtual endorsement of a candidate in a democratic election in a foreign country by a sitting U.S. president appears unprecedented in modern history.
"As far as straight-up elections, it's normally more subtle. But with Trump, nothing is subtle," Lockhart told VOA.
Riley-Smith agreed.
"There has been a long-established norm in British politics that the prime minister does not weigh in on foreign elections, and vice versa, that world leaders should not intervene in United Kingdom votes," Riley-Smith told VOA.
I'm pretty sure that compared to actual [covert] US interventions in Latin America etc., particularly during the Cold War, this pales in comparison though.
Also of note: after having left office, some US presidents have endorsed candidates in foreign elections. Obama endorsed Macron in 2017 and Trudeau this year.
It's generally not done in US politics with other functional democratic countries either, not just the UK. Doing so is simply really bad statecraft.
The problem with weighing on one side in an election in is that regardless of the result, parties and the masses who support them remember that kind of political attack. In a functioning democracy, today's losing party is likely to be the next election's ruling party. The US is going to have to deal with whichever side wins, and it could be really bad for it the day that's a party who now (quite justifiably) views the US as a political enemy.
Setting your country up as the enemy of half the electorate in a foreign nation is usually not in its long-term interest. The only time that's ever going to be worth the risk is if the spurned party is already a political enemy (for example, the Sandinista party in Nicaragua).
To horribly misquote Machiavelli, foreign political parties should be "either caressed or wiped out; because they will avenge minor injuries, but cannot do so for grave ones." So assuming that invading the country and other heavy-handed interventions are off the table, it's not a good idea for the US to be taking sides in its politics.
To counter-point my own post here, I think Trump is a special case. He has a well-earned reputation for being mercurial in his political affections. I don't think anyone at this point views him as a typical US President, or a typical Republican, or feels that anything he says is necessarily indicative of any long-term US feelings or policy (or even his own long-term feelings or policy). So were Corbyn to end up winning, it probably wouldn't surprise anyone to see Trump immediately saying all kinds of nice things about the guy, and offering all kinds of support.
This was rarely done, and was generally considered improper, until quite recently. But President Obama did it, and President Trump does it, so we may be seeing a change in what's considered usual or proper.
While making comments directly is unusual, it's not unusual for US-based political advisers to advise and even run campaigns of foreign leaders. For example, James Carville, who got Bill Clinton elected, also ran Ehud Barak's 1999 campaign against Netanyahu.
This NY Times article, describing the 1999 event, stated that, on a previous occasion, Clinton "all-but-openly endorsed" Shimon Peres in 1996. The article described James Carville as a political adviser "close to Clinton". This was in 1999. Bill Clinton was President from 1993 till 2001.
Trump's communication style, in general, is very unorthodox. He tries, as much as possible, to communicate on his own. He cuts out the proverbial middle-men from his messenges. Most famously, this is observed by his tweeting his words on his own rather than through an organized or well-managed communication office.
Not sending his political advisers and making his comments on his own is in keeping with this style. It maybe unusual, but it's not unexpected.
