The beginning of Obama’s failed policies in the Middle East was his inability to stop Israeli settlements.

As the Obama administration runs out of time and energy, an array of world leaders including Kim Jong-un, Bashar al-Assad and Vladimir Putin are celebrating their frustration of American designs.

But the unlikely source of the signature defeat of Obama’s policy agenda is no enemy, but rather a close ally and recipient of unprecedented American largesse – Israel’s Prime Minister Benjamin Netanyahu.

The failure of the Obama “red line” on settlements during his first year in office set the model for future shortcomings elsewhere, notably in Syria.

His demand for an end to the building of settlements offered a preview of his later demands upon Assad.

In both cases, United States officials believed that the fulfilment of Obama’s demand would be easy, almost self-executing.

After all, was it not clear that the tide of history could not support settlement expansion or the continued tenure of a bloody dictator who had lost legitimacy?

Ill-considered aspirations

However, both Netanyahu and Assad were reading from a different script. When they refused to roll over for the US president, Obama blinked.

Indeed, on Palestine, ineffective, ritual American protests about the ills of settlement expansion have become an embarrassment.

So too with Assad. Obama’s famous observation on Assad may have inspired his many opponents to revolt, but it has long been clear that Obama’s call for Assad’s departure in August 2011 reflected merely Obama’s ill-considered aspiration rather than a solid American policy commitment.

By soundly defeating the US president’s demand for a freeze in settlement expansion, Netanyahu was the first but not the last leader to learn that when tested Obama could be bested – that when faced with an adversary more determined than Washington to win, he did not have the courage of his convictions; that even those on the right side of history could be defied by history’s outliers and survive.

When Obama assumed office he was faced with a number of foreign policy challenges. Of all these he placed a peace agreement between Israel and the Palestinians at the top of his agenda and, at its centre, a demand for a settlement freeze.

The lesson that Obama could not even move an ally and dependent state like Israel to submit to an American policy agenda on an issue deemed critical by the US president himself was not lost on America's adversaries.

But Netanyahu had also drawn a line in the sand. “I will not keep Olmert’s commitments to withdraw and I won’t evacuate settlements,” he said “Those understandings are invalid and unimportant.”

At a March 2009 new conference, Obama pronounced “the status quo unsustainable”. Three months later, in Cairo he declared the US’ rejection of “the legitimacy of continued Israeli settlements”.

In the same declarative voice that two years later said, “The time has come for President Assad to step aside,” Obama pronounced, “It is time for these settlements to stop.”

But it was Secretary of State Hillary Clinton who offered the clearest and most sweeping definition of Obama’s settlement red line.

“[The President] wants to see a stop to settlements – not some settlements, not outposts, not ‘natural growth’ exceptions. That is our position. That is what we have communicated very clearly.”

Feeding them tales

Obama declared the achievement of a two-state solution as a US national interest, identifying a complete, permanent settlement freeze by Israel as the best instrument for establishing the diplomatic foundation to achieve its objective.

Netanyahu was initially stunned by the demand, but he rebuffed it successfully without suffering any real consequence.

He defied the wishes of the US president ? “put [the Americans] through their paces” in the words of a Netanyahu aide ? and lived not only to tell the tale, but to prosper.

In an October 31, 2009, press conference with Clinton, Netanyahu affirmed that.

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“I said we would not build new settlements, not expropriate land for addition for the existing settlements and that we were prepared to adopt a policy of restraint on the existing settlements, but also one that would still enable normal life for the residents who are living there.”

Netanyahu’s commitment to even this problematic formulation, has not withstood even a casual comparison with the facts on the ground. Settlements continue to expand with impunity.

“Everyone thinks the Americans are idiots,” wrote one Israeli journalist at the time, “and that we can continue feeding them such tales forever. Later we get insulted when Obama looks at us funny and doesn’t believe Netanyahu.”

The White House and State Department tried to minimise the collapse of policy on settlements, but they were only fooling themselves.

Cascading of poor policy choices

Everyone was watching Obama’s performance on this issue. The impression left was not, as Washington tried to convince itself, a mere setback for well?intentioned if badly executed US efforts, relevant only to the Israel-Palestine arena.

A cascading series of poor policy choices lost the Obama administration the critical policy initiative on Palestine that it was never able to recoup.

A protester waves a Palestinian flag in front of the Jewish settlement of Ofra during clashes near the West Bank village of Deir Jarir near Ramallah on April 26, 2013 [Reuters]

For a new administration seeking to place its stamp on the international scene, the failure on settlements eroded its reputation as a strong?willed and capable leader determined not only to set policy objectives but also to achieve them against friend and foe alike.

Yossi Beilin, the former Israeli deputy foreign minister, was not alone in assessing the damage suffered by Obama. “He forgot that he is the US president, and that every action of his, even killing a fly, is scrutinised by billions of eyes and every word of his is weighed and has an effect. This way, at the end of a wasted year and without any bad intentions, his statements inflicted another blow on the chances of promoting something in our region.”

The lesson that Obama could not even move an ally and dependent state like Israel to submit to an American policy agenda on an issue deemed critical by the US president himself was not lost on America’s adversaries.

The shortcomings of the administration on the settlement freeze during its first year in power were not one-off errors.

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Rather they reflect systemic shortcomings in how the administration has defined, framed and executed policy on a number of critical issues, notably Syria.

Obama misunderstood how Israeli policymakers perceive the critical, central role of settlement in occupation policy, and he was unprepared to enforce his own demand for a complete freeze in the face of unexpected Israeli opposition.

The US freeze initiative led Palestinian Liberation Organisation leader Mahmoud Abbas to miscalculate Obama’s commitment to Washington’s own policy rhetoric on settlements and led Obama to miscalculate Abbas’ ability to pursue a policy regarding renewing serious negotiations.

A freeze on settlements was meant to signal US mastery over the process and build upon this success to launch final status negotiations.

Following its failure subsequent US efforts – notwithstanding a dogged effort by Secretary of State John Kerry – never got off the ground.

Today’s result: no freeze, no negotiations, an Israeli leadership more confident of its ability to defy Washington and prosper and a loss of American credibility everywhere.

Come inauguration day, Netanyahu and Assad will not be the only antagonists to outlast Obama’s Washington – an unfortunate legacy of an American president whose good intentions provided inadequate to the task.

Geoffrey Aronson writes about Middle Eastern affairs. He consults with a variety of public and private institutions dealing with regional political, security, and development issues.

The views expressed in this article are the author’s own and do not necessarily reflect Al Jazeera’s editorial policy.