Perhaps the best example of that dismantling is in the area of campaign finance. O'Connor, onetime GOP leader of the Arizona Senate, voted to uphold landmark campaign finance legislation in 2003 only to see the court reverse that decision seven years later, after Alito replaced her.
While O'Connor was on the court, a majority of justices continued to support legislation that regulated campaign fundraising. But after her retirement and the Alito appointment, Kennedy wrote the court's 5-to-4 decision in Citizens United, the 2010 case that remade the way campaigns at every level are conducted.
The decision unleashed an ever-growing flood of cash into political campaigns. It reversed a century-old understanding that had sought to prevent corruption by barring corporations, and later labor unions, from spending their general treasury funds on candidate elections.
For Kennedy, reversing that legal understanding from the early 1900s was the realization of a long-held view of free speech.
"Political speech is indispensable to decision-making in a democracy," Kennedy wrote in the Citizens United decision, "and this is no less true because the speech comes from a corporation rather than an individual."
In general, there is probably no greater example of Kennedy's approach to the law, and how it will almost certainly differ from President Trump's nominee, than the question of how to interpret the Constitution: whether the Founding Fathers intended their creation as a static document, bound by the literal meaning of its words, or whether those words represent concepts of liberty to be interpreted over time.
In a 2003 decision that struck down a Texas law criminalizing private homosexual conduct, Kennedy said that the Founders understood that they were writing a document for the ages.
"They knew time can blind us to certain truths," he wrote in Lawrence v. Texas, "and later generations can see that laws, once thought necessary and proper, in fact serve only to oppress."
The men and women on President Trump's list of potential replacements disagree with that view, for the most part. They side with the late Justice Antonin Scalia and his successor Justice Neil Gorsuch, as well as other conservatives on the Supreme Court today, who believe the nation is bound by the original intent of the Founders.
During his presidential campaign, in a bid for the support of social conservatives, Trump issued two lists totaling 21 names and pledged to pick his first Supreme Court nominee from those lists. He did just that in naming Justice Gorsuch to fill the open seat once occupied by Scalia.
People involved in that selection process say that the president intends to expand that list a bit now. He might add Judge Brett Kavanaugh from the U.S. Court of Appeals for the D.C. Circuit, and possibly former Solicitor General Paul Clement, a highly regarded Supreme Court advocate who served in the George W. Bush administration. Clement's main drawback in the president's mind, though, is said to be that he has no judicial track record to examine.
Back in consideration are some of the names on the previous list: Judge Thomas Hardiman, of the 3rd U.S. Circuit Court of Appeals, which covers Pennsylvania, Delaware, and New Jersey, and Judge Raymond Kethledge, who serves on the Sixth Circuit, which covers a large part of the Midwest. Hardiman was the runner-up last time and is known as a staunch gun rights advocate. All four are in their early 50s.