As Donald Trump and Vladimir Putin prepare for their summit in Alaska, a review of their past meetings reveals a complicated relationship marked by moments of rapport and contention. From their initial encounters eight years ago to their more recent interactions, Trump has often left discussions with little tangible outcomes, raising questions about what might transpire this time. Historical context shows that Putin has engaged with multiple U.S. presidents over the last 25 years, each meeting bringing its own set of challenges and unpredictability. As they convene, the world watches closely to see if this summit will mirror the nature of their past meetings or if new dynamics will emerge.