In 1989, the Court issued an opinion in Webster v. Reproductive Health Services, which upheld most of the provisions of a Missouri law imposing increased regulations on abortion. The much-anticipated decision had been viewed as the death knell for the Roe case. Since 1973, four new justices had joined the Court, and three of them were considered to be unsympathetic to Roe. That change tipped the expected Roe supporters on the Court from seven to four, robbing Roe supporters of the majority they had enjoyed.

However, as chief justice and a friend of Sandra Day O'Connor, William Rehnquist suspected that O'Connor's vote was not solid. When the justices met in their conference to discuss Webster, Rehnquist spoke first and advocated a position with which he did not fully agree – that the Court should modify the Roe standard rather than overturn the decision. This was not easy for Rehnquist. He had been one of the two justices voting against the majority in Roe in 1973. Personally, he strongly advocated overturning Roe. But he also knew that without O'Connor in agreement, there would be no majority for at least eroding Roe. Rehnquist hoped O'Connor would agree with Rehnquist on most of the provisions of the Missouri statute, even if she was unwilling to go further with him to overturn Roe. Rehnquist's attempt to compromise on a core principle indicated his willingness to engage in strategic behavior to achieve his broader objective.