Sleeping with the enemy

Donald Trump’s relationship with Russia, particularly with Vladimir Putin, has been a subject of intense scrutiny and debate throughout his political career, and it remains a complex and evolving dynamic. Intrenched in decades of business ties, shaped by controversial statements, and punctuated by policy shifts in his second term as president, this relationship blends personal admiration, strategic alignment, and geopolitical consequences. Here’s a look:

Business Ties

Trump’s connection to Russia predates his political life, tied to real estate ventures and financial dealings. From the 1980s, he sought to expand his brand eastward – his 1987 Moscow trip aimed at a Trump Tower deal (never realised). Over decades, Russian oligarchs and investors bought into Trump properties, notably in Florida and New York. A 2017 Reuters investigation found at least 63 individuals with Russian passports or addresses purchased $98.4 million in Trump-branded real estate. Donald Trump Jr. acknowledged this in 2008, stating at a real estate conference that; “Russians make up a pretty disproportionate cross-section of a lot of our assets.” While not illegal, these ties fueled speculation of financial leverage, especially during the 2016 campaign when loans from Deutsche Bank with Russian co-signers raised concerns.

The 1990s and 2000s saw Trump flirt with Russian elites – hosting the 2013 Miss Universe contest in Moscow with oligarch Aras Agalarov, who later facilitated the infamous Trump Tower meeting. No concrete evidence shows Putin directly funded Trump, but these connections laid a foundation for mutual interest.

First Term of Presidency (2017-2021): Rhetoric vs. Policy

Trump’s first term showcased a duality: warm words for Putin clashed with tougher policies. He praised Putin repeatedly – calling him a “genius” and “smart” – and sided with him over U.S. intelligence at the 2018 Helsinki summit, questioning Russian election interference despite Mueller’s findings of Kremlin efforts.

Policy-wise, Trump wasn’t soft – sanctions hit Russian entities (e.g., 2017 CAATSA), and he approved lethal aid to Ukraine (Javelins). Yet, his reluctance to criticise Putin personally – unlike other adversaries – kept the relationship ambiguous. Posts on Twitter from that era, like his 2016 tweet praising Putin’s “great move” on delaying retaliation, reinforced perceptions of coziness.

Second Term of Presidency (2025-): Strategic Alignment

Since his January 20, 2025, inauguration, Trump’s relationship with Russia has sharpened into a more overt alignment, especially on Ukraine. Key developments include:

Oval Office Clash (February 28, 2025): Trump and J.D. Vance berated Zelenskyy, demanding peace talks and criticising Ukraine’s resistance. Trump reportedly admired Putin’s “strength” in contrast, aligning with his long-standing view that Putin outsmarts Western leaders.

Aid Halt (March 3, 2025): Trump’s decision yesterday to pause all military aid to Ukraine reflects a pivot toward Russia’s interests, effectively pressuring Ukraine into negotiations favourable to Moscow. Putin’s allies celebrated this as a “slap down”, while Trump excluded Ukraine from initial peace talks.

Public Statements: Trump’s praise for Putin persists – calling him “savvy” for Ukraine moves, and vowing closer ties in a Truth Social post: “Russia and I will figure this out – great relationship ahead.” (Note: I cannot confirm this. It was from a secondary source). It does, however, echo his 2016 campaign promise to “get along” with Russia.

Nature of the Relationship

Personal Admiration: Trump’s consistent praise suggests a genuine affinity for Putin’s strongman style, seen in comments like “he’s doing a great job”. Trump sees Putin as a kindred spirit; perhaps decisive, unapologetic, and anti-establishment.

Strategic Partnership: The aid halt and peace talk push – I would speculate – indicates a transactional alignment: Trump aims to end the Ukraine war quickly (for the plaudits, no doubt), possibly ceding ground to Russia, to claim a diplomatic win and Russia gains a weakened Ukraine.

No Formal Alliance: Despite optics, no evidence shows a binding pact. Trump’s moves are unilateral, driven by “America First”.

Critics: Democrats see it as capitulation, “serving Putin’s interests” or that Trump is “Putin’s puppet”.

Ramifications

Trump’s Russia tilt emboldens Putin, and for Trump I wouldn’t be surprised if some form of personal gain or leverage lurks beneath. It has proven, however, to be a relationship of convenience and admiration.

In short, Trump’s Russia bond blends decades of financial flirtation and personal respect for Putin. For decades Russia has been enemy number 1 to America, and to use an old cliche (or movie line) Trump is sleeping with the enemy.

 

 

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