Considering that conventional invasion would have precipitated nuclear war, Reagan was being as aggressive as possible without ending the world.
Your analogy just doesn't hold water. It certainly doesn't square with anything Churchill ever said or did, since Winston would have rolled on Moscow if he'd had the armor and other resources to do it.
That's why your screenname is such a sick joke.
How do you know that? He made an alliance with Stalin. He loathed Stalin and communism, but I haven't read anywhere that he advocated invading the Soviet Union - or that he would have supported such an invasion if Britain had greater military power. In fact, he vehemently opposed proposals for the Western powers to to invade China, after WWII, to help the Nationalists in their fight against Mao and the communists. Churchill was not reflexively in favor of each and every military action that might be proposed, even if the target was a dictator. It's not inconsistent to be a fan of Churchill and to believe that the US invasion of Iraq was unnecessary (and possibly even harmful to our interests). Saddam may have been as evil as Hitler in some respects, but, in his weak and contained position, he didn't pose a threat to the US the way Hitler, with his growing military might and his occupation of neighboring territories, threatened Europe and the world in the 1930s. Saddam was about as much a threat to us as Castro. And haven't seen any freepers arguing for an invasion of Cuba. Historically, we don't invade countries just because the leaders are evil. Churchill certainly didn't. It requires a real imminent threat to justify invading another country.