President Barack Obama was often accused of playing ruthless “Chicago politics” by his Republican enemies. But Obama’s biggest mistake lay not in cynicism but misplaced idealism.

Obama Mistake No. 5: Believing that public and private employers would voluntarily comply with the law.

The Affordable Care Act (ACA) requires employers to provide insurance for part-time employees who work more than 30 hours per week. Yet many employers claimed–without having to offer proof–that they couldn’t afford it.

So they limited part-time workers’ hours to 29 per week instead.

Obama was clearly surprised at this. But he shouldn’t have been.

Greed-fueled businessmen always try to avoid complying with the law–or achieve minimum compliance with it.

The Act doesn’t penalize companies for not providing health insurance coverage for part-time employees who work fewer than 30 hours.

Predictably, employers:

• Moved fulltime workers into part-time positions;
• Refused to provide their employees with medical insurance; and
• Avoided fines for non-compliance with the law.

Some employers openly showed their contempt for President Obama–and the idea that employers have any obligation to those who make their profits a reality.

One was John Schnatter, CEO of Papa John’s Pizza, who said:

• The prices of his pizzas would go up–by 11 to 14 cents per pizza, or 15 to 20 cents per order; and
• He would pass along these costs to his customers.

 John Schnatter

“If Obamacare is in fact not repealed,” he told Politico, “we will find tactics to shallow out any Obamacare costs and core strategies to pass that cost onto consumers in order to protect our shareholders’ best interests.”

Thus, President Obama should have required all employers to provide insurance coverage for all of their employees, regardless of their fulltime or part-time status.  

This would have produced two substantial benefits:

1. All employees would have been able to obtain medical coverage; and
2. Employers would have been encouraged to provide fulltime positions rather than part-time ones.

Employers would thus feel: “I’m paying for fulltime insurance coverage, so I should be getting fulltime work in return.”

If Obama considered this option, he decided against pressing for it.

Obama Mistake No. 6: Failing to closely study his proposed legislation.

Throughout his campaign to win support for the ACA, Obama had repeatedly promised: “If you like your health insurance plan, you can keep your plan. If you like your doctor, you can keep your doctor. Period.”

But the 906 pages of the law held a fatal catch for the President’s own credibility.

The law stated that those who already had medical insurance could keep their plans–so long as those plans met the requirements of the new healthcare law.

If their plans didn’t meet those requirements, they would have to obtain coverage that did.

But many Americans wanted to keep their current plan–even if it did not provide the fullest possible coverage.

Suddenly, the President found himself facing a PR nightmare–charged and ridiculed as a liar.

Even Jon Stewart, who on “The Daily Show,” had supported the implementation of “Obamacare,” ran footage of Obama’s “you can keep your doctor” promise.

Jon Stewart

The implication: You said we could keep our plan/doctor. Since we can’t, you must be a liar.

All of which points to a final warning offered by Niccolo Machiavelli: Whence it may be seen that hatred is gained as much by good works as by evil….  

Former Democratic Presidential nominee Hillary Clinton said that, if she were elected, she would seek incremental changes in the ACA. That possibility became moot when she lost the 2016 election to Donald Trump.

Vermont U.S. Senator Bernie Sanders, on the other hand, wants a single-payer plan.

A single-payer plan would prove simpler and more comprehensive than the ACA. But the chances of its passing a Republican-dominated Congress are absolutely zero.

The election of Donald Trump seems to have finally doomed the ACA–except for one thing: Since it became law, in 2010, 22 million Americans who had never before obtained healthcare insurance now have it.

This includes even Republicans who voted for Trump–without realizing they would be losing their only tie to medical care.  And now many of them are finally realizing this truth.

Thus, Republicans in the House and Senate now find themselves besieged by angry constituents at town hall meetings.

These Republicans care nothing for Americans who would be left without medical care. But they do care about their own futures–as members of Congress.

This has led to three schisms among Republicans:

• Those who still demand the complete repeal of “Obamacare.”
• Those who want the Act repealed and then replaced with an entirely different healthcare plan–which Republicans have yet to agree on. Developing this could literally take years–during which time former ACA members would have no insurance.
• Those who want Republicans to first create an alternative healthcare plan, win its Congressional approval, and then repeal the Act.

Republicans expect Democrats to sign on with their “Obamacare replacement plan.” But Democrats have made it clear: “You repeal it, you’re on your own in replacing it.”

Republicans spent eight years demanding the repeal of “Obamacare.” But now they fear that its repeal will lead to the repeal of their own political ambitions.

Barack Obama was easily one of the most highly educated Presidents in United States history. He is a graduate of Columbia University (B.A. in political science in 1983).

In 1988, he entered Harvard Law School, graduating magna cum laude–“with great honor”–in 1991.

He was selected as an editor of the Harvard Law Review at the end of his first year, and president of the journal in his second year.

President Barack Obama

He then taught Constitutional law at the University of Chicago Law School for 12 years–as a Lecturer from 1992 to 1996, and as a Senior Lecturer from 1996 to 2004.

Yet, his signature plan to give every American access to healthcare, the Affordable Care Act–universally known as “Obamacare”–remains stricken with dangerous flaws.

So where did he go wrong?

Several ways–in all, at least six.

Obama Mistake No. 1: Putting off what people wanted while concentrating on what they didn’t.

Obama started off well when he took office. Americans had high expectations of him. This was partly due to his being the first black to be elected President.

And it was partly due to the disastrous legacies of needless war and financial catastrophe left by his predecessor, George W. Bush.

Obama entered office intending to reform the American healthcare system, to make medical care available to all citizens, and not just the richest.  But that was not what the vast majority of Americans wanted him to concentrate his energies on.

With the lost of 2.6 million jobs in 2008, Americans wanted Obama to find new ways to create jobs. This was especially true for the 11.1 million unemployed, or those employed only part-time.

Jonathan Alter, who writes sympathetically about the President in The Center Holds: Obama and His Enemies, candidly states this.

But Obama chose to spend most of his first year as President pushing the Affordable Care Act (ACA)–which would soon become known as Obamacare–through Congress.

The results were:

• Those desperately seeking employment felt the President didn’t care about them.
• The reform effort became a lightning rod for Right-wing groups like the Koch-brothers-financed Tea Party.
• In 2010, a massive Rightist turnout cost the Democrats the House of Representatives, and threatened Democratic control of the Senate.

Obama Mistake No. 2: He underestimated the amount of opposition he would face to the ACA.

For all of Obama’s academic brilliance and supposed ruthlessness as a “Chicago politician,” he displayed an incredible naivety in dealing with his political opposition.

Niccolo Machiavelli (1469-1527), the Florentine statesman and father of modern politics, could have warned him of the consequences of this–through the pages of The Prince, his infamous treatise on the realities of politics.

Niccolo Machiavelli

And either Obama skipped those chapters or ignored their timeless advice for political leaders.

He should have started with Chapter Six: “Of New Dominions Which Have Been Acquired By One’s Own Arms and Ability”:

…There is nothing more difficult to carry out, nor more doubtful of success, nor more dangerous to handle than to initiate a new order of things.  

For the reformer has enemies in all those who profit by the old order, and only lukewarm defenders in all those who would profit by the new order, this lukewarmness arising partly from fear of their adversaries, who have the laws in their favor, and partly from the incredulity of mankind, who do not truly believe in anything new until they have had actual experience of it.  

This proved exactly the case with the proposed Affordable Care Act.

Its supporters–even when they comprised a majority of the Congress–have always shown far less fervor than its opponents.

This was true before the Act became effective on March 23, 2010. And it has remained true since, with House Republicans voting more than 60 times to repeal, delay or revise the law.

So before President Obama launched his signature effort to reform the American medical system, he should have taken this truism into account.

Obama Mistake No. 3: Failing to consider–and punish–the venom of his political enemies.  

The ancient Greeks used to say: “A man’s character is his fate.”  It was Obama’s character–and America’s fate–that he was by nature a man of conciliation, not conflict.

Richard Wolffe chronicled Obama’s winning of the White House in his 2009 book, Renegade: The Making of a President. He noted that Obama was always more comfortable when responding to Republican attacks on his character than he was in making attacks on his enemies.

President Obama came into office determined to find common ground with Republicans.

But they quickly made it clear to him that they only wanted his political destruction. At that point, he should have put aside his hopes for a “Kumbaya moment” and re-read what Niccolo Machiavelli said in The Prince on the matter of love versus fear:

From this arises the question whether it is better to be loved or feared, or feared more than love. The reply is, that one ought to be both feared and loved, but as it is difficult for the two to go together, it is much safer to be feared than loved.