With more than 30 years on the Supreme Court, Justice Anthony Kennedy has made impact after impact on American life.

Appointed by President Ronald Reagan in 1988, Kennedy has long been the court’s most flexible conservative and, on no shortage of occasions, has sided with liberal justices over some of his right-leaning colleagues. Thanks to his penchant for examining cases beyond political ideology, Kennedy became not only unpredictable, but often times the deciding factor in some of the country’s most critical cases.

In a letter to President Trump on Wednesday morning, the 81-year-old justice revealed his intent to retire — ultimately paving the way for Trump to install a new judge who could hold on to the seat for decades to come.

Here’s a look at few of Kennedy’s key cases during his tenure on the Supreme Court:

Gay Rights

Kennedy in 2015 penned the ruling that legalized same-sex marriage nationwide.

“No longer may this liberty denied. No union is more profound than marriage, for it embodies the highest ideals of love, fidelity, devotion, sacrifice and family,” it reads.

“In forming a marital union, two people become something greater than they once were.”

The final paragraph in Kennedy’s ruling has since been used by scores of couples in their wedding vows.

Citizens United

He was also instrumental in the 2010 Citizens United ruling, which dubbed political spending by independent corporations and unions a form of free speech protected by the First Amendment. Those opposed feared unfettered spending by wealthy business could have a strong influence on election outcomes.

In the case, the conservative nonprofit Citizens United sought to air a film critical of Hillary Clinton and to advertise for it during broadcasts leading up to the 2008 Democratic primary election. Federal law at the time prohibited any business or union to broadcast an ad reaching over 50,000 people within 30 days of a primary or 60 days of an election.

The decision overruled the U.S. District Court for the District of Columbia and effectively reversed two previous Supreme Court decisions.

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“If the First Amendment has any force, it prohibits congress from fining or jailing citizens, or associations of citizens, for simply engaging in political speech,” Kennedy wrote.

“When the Government seeks to use its full power, including the criminal law, to command where a person may get his or her information or what distrusted source he or she may not hear, it uses censorship to control thought. This is unlawful. The First Amendment confirms the freedom to think for ourselves.”

Abortion

In 1992, Kennedy disappointed conservatives when he co-wrote an opinion reaffirming the outcome of Roe vs. Wade, which recognizes abortion as a constitutional right.

In the case of Planned Parenthood vs. Casey, it seemed an initial majority of five justices were willing to effectively overturn Roe, but Kennedy changed course following an initial conference on the matter.

“These matters involving the most intimate personal choices a person may make in a lifetime, choices central to personal dignity and autonomy are central to the liberty protected by the Fourteenth amendment,” he wrote.

“At the heart of liberty is the right to define one’s own concept of existence, of meaning, of the universe and of the mystery of human life.”

Travel Ban

Kennedy on Tuesday joined in the majority opinion of Chief Justice John Roberts’ upholding the third iteration of President Trump’s travel ban, which bars visitors and refugees from five mainly Muslim nations — Iran, Libya, Somalia, Syria and Yemen — as well as travelers from North Korea and government officials from Venezuela.

“The proclamation is squarely within the scope of Presidential authority,” Roberts wrote.

In his brief concurrence, Kennedy agreed Trump did not overreach in implementing the ban, noting that just because it is within the scope of his powers does not mean he should do it.

The fact that “an official may have broad discretion, discretion free from judicial scrutiny, makes it all the more imperative for him or her to adhere to the Constitution and the meaning of its promise.”

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