During the 2016 presidential election, I had the feeling that Barack Obama was not very enthusiastic about the candidacy of Hillary Clinton.  His rare rallies in support of Hillary were not energetic enough and were held in the same style.  Obama told the audience about the successes of his administration, and in the end, he casually introduced Hillary and asked supporters to vote for her in the election.  It seemed that he was simply fulfilling his duties to the party but would have preferred to spend time elsewhere.

A hypothesis was formed in my head that, in reality, Obama did not want Hillary to win and, if possible, sabotaged her election campaign.  At first glance, this proposal seems unrealistic; however, even Hillary herself gently hinted that Obama could have used his time and authority more efficiently in supporting her.

In recent years, facts have been revealed that both support and refute this theory.  Let us consider arguments in support of the suggestion.  First of all, it should be noted that the Democratic Party was not homogeneous; it consisted of many clans and poles of influence.  During the 2008 election campaign, the party was divided into two major camps: the left-centrist and more traditional wing supporting Clinton and the openly far-left, more energetic, and younger wing backing Obama.

These two wings were quite hostile to each other; their undercover bulldog fights often went outside.  Clinton's clan considered Obama a new, inexperienced individual whose time had not yet come and who had the audacity to block the road to the future first female president.  They tried to bring him down with all possible measures.  For example, the movement that questioned Obama's birthplace and citizenship, so-called "birthers," originated among Clintonites.  Only much later did this movement begin to include Republicans in its core.

Obama humiliated Clinton during the debate and his rallies.  The situation had reached a boiling point, as hatred between clans could cost the Democratic Party elections.  Formal reconciliation and the unification of groups around Obama took place in the house of the skilled apparatchik Dianne Feinstein.  It was decided that Obama would become the candidate for the Democrats, and Clinton would receive an important and prestigious post of secretary of state in the case of a victory.  Obama followed Sun Tzu's advice, keeping his friends close and his enemies closer.  Of course, formal reconciliation did not lessen Obama's and Clinton's deep hostility to each other, but they played the roles of good comrades in front of the public exceptionally.

After eight years in the White House, Barack and Michelle Obama emerged as charismatic leaders, greatly respected by a significant number of Democrats and many foreign nations.  At some point in time, the couple decided that they have fairly broad support and popularity, which could be converted into Michelle Obama's presidency.  However, Michelle could not run for president immediately after Barack, according to early agreements with Hillary and the Democratic elite.  Besides, it would not look very good in the eyes of voters.  She had to skip a term but somehow keep soldiers in the trenches.

It is known that the president becomes an informal leader and representative of the party that wins the election.  Obama worked hard to appoint his people to all branches and levels of power, including the Democratic Party.  In other words, he had strengthened the clan that was supposed to benefit him after the presidency.  He laid the foundations for Michelle's presidential bid.

What would the Obama couple face if Hillary Clinton won the presidential election?  Knowing the history of their relationship, the personal qualities of Hillary, and her harsh actions to destroy her enemies, we can assume with great certainty that Clinton would begin to methodically and systematically dismantle Obama's clan and legacy.  As a new head of the Democratic Party, she would start by assigning her functionaries to all levels of the Democratic hierarchy and redirecting financial flows to Clintonites.

Remember, during a rally, Bill Clinton once said, "We have to leave behind these horrible eight years."  After that revelation, Bill was not seen at Hillary rallies anymore.  Obama understood that the only person who had guts to tear off a structure built by the first black president and encroach on his legacy would be an unforgivable and vindictive Hillary.  Therefore, Obama faced a dilemma — to sincerely support Clinton, but in the end, to lose both the party infrastructure and financial flows, or to pretend he supported the candidate of the Democratic Party but at the same time wished her a loss.  

This article posits that it was more profitable for Obama in the 2016 election cycle to have a Republican as the next president.  Several logical constructs support this proposition.  They are based on the assumption that Obama was more concerned with his own legacy, his wellbeing, and the political future of his family than with the prosperity of his party or country.

First, Obama knew very well that Trump would criticize him and pursue a policy contrary to his.  It was inevitable.  But, having a Republican president would preserve Obama's party infrastructure, his influence on it, and his relationship with sponsors.  Besides, Obama would have many leftovers in the executive branch of bureaucracy.  All of the above would strengthen Michelle's bid for returning to the White House.

Secondly, as far as his political and economic heritage is concerned, Obama would prefer that his legacy not be altered.  However, if someone dared to touch it, he would favor Republicans doing so rather than Democrats.  In the former case, he would have an excellent talking point, blaming a political turn on malicious Republicans.  Obama could claim that if it had not been for the interference of Republicans, his policies would have made America prosper, but, unfortunately, the progress was stopped by these evil right-wingers.  Michelle, as a presidential candidate, would greatly capitalize on such an explanation of events.

Even if we assume that Michelle will not run, Obama would stick to such an interpretation of his reign.  He has already started to claim that he saved the country from depression and that current economic success is due to his policies. 

Thirdly, Obama hoped that Trump would be a weak president who would be easy to overthrow in four years.  To the disappointment of the Obama couple, Trump turned out to be a great president.  The success of the country under his leadership is impressive, and it will be almost impossible to defeat him in the 2020 elections.

Obama's political strategists are pretty smart guys and advised Michelle to skip the 2020 elections.   She would have easily defeated the current Democratic candidates, who are strikingly weak and vulnerable, but she would have stumbled on Trump.  As he did in 2016, Obama keeps a low profile and does not support anyone, not even his vice president, Joe Biden.  It seems that Obama understands that not one of the Democratic candidates has a chance in 2020.

As a side effect, this hypothesis explains the erratic and illogical behavior of the former FBI head James Comey.  He closed the Clinton case, then opened it again, and, at the same time, was unable to bring charges against her.  As an Obama man, he somewhat undermined Clinton's chances of winning, but at the same time, he saved her from prison.  This was a subtle game that does not have a rational explanation unless you remember that it was beneficial to Obama's goal.

This theory can be partially falsified if Michelle does not run in 2024, or if future investigations find a piece of evidence that Obama personally directed spying on Trump's campaign to overthrow him.  Time will tell, but, for now, this theory seems plausible.