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Robert’s Rules of Chess

By Oliver DeMille

When Chief Justice Roberts sided with the liberals to uphold Obamacare, it sent a shock wave through conservatism.

After all, Mitt Romney had lauded Roberts as the example of the kind of Justices he’d select if elected president, and Roberts was seen as a clear conservative by most Republicans.

With one vote, he angered half the nation and left many feeling betrayed.

But was Roberts playing chess while the rest of the nation engaged in checkers? Was his decision on Obamacare a Fork, a Pin or a Sac?*

Here are a few reasons why his decision may be an Exchange Advantage* in a long game, a strategic risk that could pay significant positive gains for conservatives in the years ahead:

  1. It put the Obamacare law front and center in the 2012 election, and since Obamacare is overwhelmingly unpopular—even among swing voters who will determine the election—this is a huge potential boost for Romney.
  2. It allows Republican candidates for the House and Senate to make a wildly unpopular law, Obamacare, a key reason to elect them in November. It creates a much stronger possibility of a Republican sweep (House, Senate, and White House).
  3. Few Americans pay attention to Supreme Court cases, so the few that get wide notice like Obamacare are a chance for the Court to make a splash. Roberts used this to boost the status of the Court. The White House, Congress, the states and the people now take the Court more seriously than ever before, and Roberts himself is a real player in Washington and the whole nation—no longer a minor player, but a central figure in everything Washington does.
  4. Roberts is now respected and feared by opponents in a way he never was before, and in a Marshall-like way that few Chief Justices have enjoyed. He can use this in the future by letting it be known how he might feel about a certain law or policy before it is enacted.
  5. Roberts has struck a blow to the view that the Court is all political, all of the time. Liberals can only attack cases by saying they hate a given case (e.g. Citizens United), not the conservatively-dominated Court. This creates significant opportunity for the Court to make conservative rulings more free from charges of politics.
  6. By siding with the Left in this decision, Roberts insulated himself for decades (maybe for the rest of his career) from criticism by the Left. Just as Obama can say, “Osama bin Laden” and shut down any suggestions of being soft on national security, Roberts can say “Affordable Health Care Act” and insulate himself and the Court against any criticism that the Court is just a branch of the Republican party.
  7. By siding with the liberals, Roberts got to write the Majority Opinion in a way that ruled the individual mandate a “tax.” This is very significant because:
    • This makes it likely that Republicans in Congress can repeal parts of Obamacare using reconciliation, which would only take 51 Senators rather than 60.
    • It also makes Obamacare a massive tax, the biggest tax hike in American history. This reality isn’t lost on the American people or on the Obama Administration. It immediately put the Obama campaign on the defensive: President Obama said it wasn’t a tax, but his lawyers argued at the Court that it was a tax. Taxes aren’t popular, and such a massive tax will likely become increasingly unpopular over time.
  8. Roberts used the opinion to decrease the power of Washington over the states by arguing that Obamacare would have been unconstitutional under the Commerce Clause or the Necessary and Proper Clause. This is one of the few rulings since the Great Depression that actually reduces the power of the federal government. Roberts may use the precedent of this case to strike down many federal programs in the future that cannot be considered a tax. If this happens, this case will be seen as the time where the era of big government was legally reversed.
    • On one hand, this is a strange way to put a legal end to big government. But this is not unprecedented. The Court has used various cases to rule on things that aren’t the direct focus of the case (see, for example, the United States v. Butler, 1936).
    • On the other hand, Roberts will probably never again have a case so publicized and likely to be considered by most Americans—which makes this the perfect case to create such a precedent and announce such an intention.
    • By announcing such a direction of the Court—to begin sizing down government—in this case, he made it very unlikely that President Obama or other liberal leaders would attack this change even though it strikes directly at their goals.
  9. This decision, more than any other event in 2012, increased the likelihood of Romney winning in November and nominating 1-3 Republican Justices to the Court during his presidency, and of electing more Republican Senators who confirm Justices that are nominated. This, above all, may be a long-term Roberts strategy. The question may have been: Is it worth the risk of upsetting conservatives in order to help get a strongly conservative court for the next two decades or more?
  10. Roberts appears to really believe that the individual mandate in Obamacare was unconstitutional under the Commerce and/or Necessary and Proper Clauses but constitutional as a tax. He called President Obama’s bluff, and this precedent will force any future law with a mandate to openly call it a tax. This is a blow to liberalism and a victory for conservatism.
  11. The Court can still rule on Obamacare in the Virginia case in 2015 or other cases that arise after Obamacare is implemented in 2014 and after. Indeed, the Court can use the precedent of a more narrow view of the commerce clause from the recent Obamacare case to strike down excesses of Obamacare in the years ahead. If Obama wins in 2012, the Court can re-rule and strike down various provisions on new grounds.

Some of us really like checkers, and if the 2012 election goes poorly for conservatives and the government continues to spend, regulate, borrow and socialize, many will look back on the Obamacare ruling as a mile marker in the loss of freedom.

I, for one, think the mandate was never meant to be a tax and as such is clearly unconstitutional.

In the parlance of another popular game, I think we should call a spade a spade.

But I do understand the idea that strategic risk is sometimes necessary to get a big win instead of a small one.

A case that creates as much passion as Obamacare only comes along rarely, and Roberts seems to have seen this as an opportunity to strike a powerful blow at the opposition.

Big government has been gaining momentum for a long time, and Robert’s risk may yet prove a brilliant maneuver that begins the reversal of bad Court decisions starting with Marbury v. Madison (1803).

I’m not holding my breath, but the optimist in me says that maybe, just maybe, this was a game-changer for freedom. Roberts may well have put his opponents en prise.*

At the very least, this is possible, and after so many decades of going in the wrong direction, I’m excited with the mere possibility of an effective freedom warrior among our top leaders.

Often one move is the difference between black queen or white queen to checkmate.

Time will tell.


* Chess Glossary

A Fork is an attack on two or more pieces simultaneously.

A Pin is where a piece may not be moved because another piece would be subject to capture.

A Sac is a voluntary offer of material for compensation in space, time, Pawn structure, or even force. A Sac can lead to an advantage in a particular part of the board. Note that a Sac is not always calculable and often entails an element of uncertainty (Also known as a Sacrifice).

In an Exchange Advantage, a player trades a piece for an enemy piece of greater value.

A chess piece is ‘En Prise‘ if it is left or moved to a square where it can be captured without loss to the capturing player.


(By the way, the best article I’ve seen on the Obamacare discussion is “We’re Having the Wrong Debate about Health Care” by Stephen Palmer)


odemille 133x195 custom Egypt, Freedom, & the Cycles of HistoryOliver DeMille is the chairman of the Center for Social Leadership, and a co-creator of Thomas Jefferson Education.

He is the author of A Thomas Jefferson Education: Teaching a Generation of Leaders for the 21st Century, and The Coming Aristocracy: Education & the Future of Freedom.

Oliver is dedicated to promoting freedom through leadership education. He and his wife Rachel are raising their eight children in Cedar City, Utah.


  1. Oliver, I’m neither conservative nor liberal, so my attitude towards the Robert decision has been theoretic and curious. I enjoyed this article a lot. We can’t know exactly what was going on in his head, but some of your guesses are highly instructive about statesmanship.

  2. Tom Manzer says

    Awesome summary. Looking for the positive in the appearance of a negative decision is true vision. Thank you for your insight!

  3. Excellent break down Oliver. I’m considered an idea like this as well, though man of the options you listed came to mind. What stood out to me was the fact that if the ACA mandate is a tax, then it is also unconstitutional because it originated in the Senate and all revenue bills must originate in the House. If this was Roberts plan, however, then he should have said something right away after the decision was announced.

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