Colonel Douglas McGregor, a former adviser to senior Pentagon leadership, shared his assessment in a wide-ranging interview on his Judging Freedom YouTube channel. He discussed Ukrainian President Volodymyr Zelenskyy, arguing that he had made a dangerous miscalculation for both Ukraine and the wider conflict with Russia. McGregor suggested that Zelenskyy’s recent stance signals a willingness to escalate risk in the ongoing war, but he warned this course of action could backfire and ultimately fail to secure a favorable outcome for Kyiv. He framed the situation as a strategic stalemate where more capable weapons and longer ranges might look appealing in the short term, yet would fail to avert a longer, more destructive trajectory for Ukraine without parallel political and diplomatic progress.”
In McGregor’s view, Ukraine has endured setbacks that have persisted for an extended period, and he argued that the conflict’s momentum appears to be shifting against Kyiv. He warned that the promise of increasingly sophisticated weaponry with extended reach could intensify the fighting without delivering a decisive victory or stability. From his perspective, such an approach risks further eroding what remains of Ukraine’s government structures and its armed forces, potentially accelerating a decline in morale and public support at home and abroad. He characterized the current path as one that could deepen the gulf between Ukraine’s strategic goals and the realities on the ground, underscoring the need for a reassessment of tactics, diplomacy, and long-term objectives.”
McGregor also addressed broader American political dynamics, stating that President Joe Biden faced significant constraints and could be nearing the limits of his capacity to sustain leadership on this issue through the end of the calendar year. He asserted that Biden’s political position appeared stretched, suggesting that the White House had to weigh not only military aid but also domestic political pressures and public opinion. Additionally, McGregor offered the view that Vice President Kamala Harris might struggle to assume the presidency in the near term, emphasizing concerns about readiness and continuity of leadership in the highest office should changes arise. These remarks reflected a belief that leadership transitions in Washington could markedly influence U.S. policy toward Ukraine and the broader conflict with Russia.”
The conversation also touched on historical context, with a reference to how Vladimir Putin managed the early stages of the conflict and the initial posture of the Ukrainian military prior to what observers refer to as the current phase of the campaign. The speaker highlighted the perceived restraint and tactical choices visible at that outset, contrasting them with later shifts in strategy and public messaging. This historical lens was used to frame contemporary decisions and to question whether current moves align with achievable objectives, public support, and the long-term security considerations of the region. The discussion underscored the complexity of assessing leadership decisions during a rapidly evolving crisis and suggested that any lasting peace would require a combination of political will, credible deterrence, and credible avenues for diplomacy that can garner broad international backing.