One of my favorite stories about Supreme Court Justice Oliver Wendell Holmes is from one of his train trips to Washington. Holmes forgot his ticket but the train conductor reassured him, “Do not worry about your ticket. We all know who you are. When you get to your destination, you can find it and just mail it to us.” Holmes responded, “My dear man, the problem is not my ticket. The problem is, where am I going?”

Chief Justice John Roberts may have the same uncertainty this week as he finds himself on track to two decisions that will define him and the court. Once heralded as a reliable conservative, Roberts became the swing vote with the retirement of Justice Anthony Kennedy. Now conservatives are unsure if Roberts will deliver or deflect a coup de grâce with decisions on ObamaCare and abortion. In both cases, he will grapple with his previous views that would push him to vote for decisions with sweeping impacts. For a chief justice who gets sticker shock at such moments, Roberts may find himself evading his prior self in shaping the future court.

Affordable Care Act

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The Supreme Court earlier this week accepted an appeal from various states that are controlled by Democrats who seek the reversal of lower courts striking down the individual mandate provision of the Affordable Care Act. In 2012, Roberts saved ObamaCare as the fifth vote in the case of National Federation of Independent Business v. Kathleen Sebelius. In my view, it was one of his weakest opinions as chief justice.

Roberts sided with the conservative justices that requiring individuals to buy insurance was a flagrant violation of federalism guarantees, a view I shared. But in what read like a last minute addition, he voted with the four liberal justices in declaring that none of that matters because he viewed the individual mandate as a tax. It was a surprising turn, since both sides had denied that this was a tax. But by declaring the individual mandate an exercise of the taxing authority of Congress, Roberts saved the law. He insisted the individual mandate was the thumping heart of ObamaCare, which could not survive without its tax revenue from the healthy young citizens who would pay more into the system than they took out.

His decision, refashioning the mandate as a tax, appeared artificial and opportunistic to many of us. It also sowed the seeds of its own destruction by not just resting the survival of ObamaCare on the existence of the tax but by insisting that the law could not survive without it. Congress called his bluff by zeroing out the tax, which was the very thing that Roberts had said was needed to sustain ObamaCare as a constitutional matter.

The case is now headed to Roberts again. The lower courts had quoted him and relied on his reasoning to declare the provision unconstitutional. The district court struck down the entire law based on his 2012 decision. The appellate court left open the possibility that the entire law could be struck down but remanded that question back to the district court.

Roberts is well known for resisting dramatic social or political changes in opinions. However, he will now be faced with a determined protagonist in himself. In order to save ObamaCare again, he will have to brush aside his own analysis from 2012, fueling objections that the 2012 rationale was a convenient and transparent ruse to avoid the need to strike down the law. The case of California v. Texas presents the question in the sharpest relief. The tax fallacy is now evident, but Roberts could still declare “long live ObamaCare” based on a federal tax that brings in no revenue.

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Roe v. Wade

The Supreme Court this week will also return again to the long simmering debate over the ability of states to limit abortions or abortion services. As with critics of ObamaCare, pro-life advocates have long viewed Roberts as, at best, a fair weather friend and, at worst, a furtive foe on the issue of abortion. The case of June Medical Services v. Stephen Russo will again be forced into the open on a key constitutional question.

There is not a lot of room left to avoiding declaring whether a state like Louisiana can impose conditions on abortion services, such as requiring that physicians have admitting privileges at a local hospital. What is most striking about the case is that it involves very similar issues as in Whole Woman’s Health v. John Hellerstedt in 2016, but it will be argued to a different court. Roberts voted in the minority when there was no chance the Supreme Court would open up abortion to state limitations.

Kennedy, a critical swing vote for pro-choice advocates, was replaced by Justice Brett Kavanaugh, who was controversial because of his perceived hostility toward the foundation of Roe v. Wade. The vote was five to three because Justice Antonin Scalia had passed and Justice Neil Gorsuch had not yet been confirmed. With Scalia or Gorsuch, the vote might have been five to four. With Kavanaugh, however, the result would flip.

The Louisiana case presents that same type of restrictions as the Texas case and comes from the same circuit. In the Texas case, the fear was that limitations would dramatically reduce the number of abortion clinics. In the dissent that Roberts joined, Justice Samuel Alito rejected claims of a causal link between such limitations and the reduction of the number of clinics. Critics of the Louisiana law argue that same causal link, with a bigger potential to cut the number of clinics in the state to one.

Roberts will have to vote on a Supreme Court that can clearly deliver a victory for states' rights and pro-life advocates. There are technical “off ramps” with both cases, but he will have to work hard to evade this clear vote. Clarity is something that Roberts likely does not relish in either area. On both ObamaCare and abortion, he would have to reject his own prior analysis to vote against the position of his conservative colleagues. So conservatives may not like the new destination of the chief justice if he decides to jump the track on both of his prior landmark decisions.

Jonathan Turley is the Shapiro Professor of Law with George Washington University. He served as lead counsel for the House of Representatives in litigation over the Affordable Care Act. He is on Twitter @JonathanTurley.