In 1490, he acted as a personal bodyguard for German ambassador Georg Delator, who had come to Moscow at the request of Maximilian I.
During the reign of Vasili III, Beklemishev began to fall into disgrace as a man known for his stern disposition and oppositionary opinions (e.g., he believed that the right to discuss the affairs of the state was the most essential prerogative of the boyardom).
At one point during a debate in the Duma, Vasili III told Beklemishev: "Get out of my sight, you smerd, I don’t need you anymore!".
After this incident, Ivan Beklemishev was constrained to retire from the royal court and the affairs of the state.
Later, he began to express his dissatisfaction with the tsar’s policies in his discussions with Maximus the Greek, for which he would pay dearly.