Obama surged tens of thousands of additional US troops into Afghanistan, but when he gave a speech at West Point on December 1, 2009, announcing the new troops, he also simultaneously announced their withdrawal date.
For the Taliban, the Afghan government and Afghanistan's neighbors such as Pakistan, the headline of Obama's West Point speech was not the surge of new troops, but the withdrawal date. This had the counterproductive effect of encouraging the Taliban to wait out the Americans.
It also undermined confidence among Afghans and it affected the hedging strategy of Pakistan's military intelligence service, ISI, which has long supported elements of the Taliban.
The Trump administration won't replicate this mistake --there will be no announcements of withdrawal dates, according to the US official.
Getting the Afghanistan strategy right not only could determine the fate of America's longest war, but also could have a powerful impact on America's role in South Asia. But there are serious risks and working through all of them is extremely difficult, as the George W. Bush and Obama administrations discovered.
As to the number of additional American troops going to Afghanistan, last week President Trump delegated that decision to Defense Secretary James Mattis.
The US official put the number of new troops that is expected to deploy to Afghanistan at 3,800, adding to the 8,400 that are already there.
The delegation of authority to Secretary Mattis is another break with the Obama White House, which capped the number of troops that could be deployed.
The addition of the 3,800 troops will allow the Americans to train and assist Afghan forces at the tactical level on the ground, just as the US military is currently doing in Iraq with the Iraqi forces fighting against ISIS.
The addition of new troops is part of a broader South Asia strategy that the Trump administration is formulating that will include how to deal with Afghanistan's neighbors such as Pakistan. The new South Asia strategy will be finished in the "coming weeks," according to the senior US official, and it will focus as much on aid and diplomacy as it does on military strategy.
The senior US official said that the rush to add troops before the overall South Asia strategy was set was the result of the worsening security and political situation in Afghanistan that was particularly underlined by a massive truck bomb that blew up in Kabul's diplomatic quarter on May 31, killing more than 150.
The bombing and other recent terrorist incidents has amplified major divisions in the government, which is led by both President Ashraf Ghani and CEO Abdullah Abdullah, according to the US official.
An awkward shotgun marriage between Ghani and Abdullah was engineered by the Obama administration after both of them contested the 2014 presidential election and accused each other -- correctly -- of benefiting from widespread electoral fraud.
Situation is 'critical'
The Trump administration worries that if the Afghan government were to fracture so, too, would the Afghan army. Describing the situation as "critical," the US official said that is why the addition of new troops could not wait for the completion of the overall South Asia strategy.
To skeptics who say that America's longest war --- now in its 16th year in Afghanistan --- seems unlikely to be turned around by the addition of a relatively few number of troops that are being added by the Trump administration, compared to the tens of thousands of additional soldiers that President Obama deployed in 2009, the US official pointed to four factors that may produce a better result:
First, the long-term American commitment to Afghanistan by Trump gives time to stabilize the country so that the Afghan army can have the time and space to handle internal security.
Second, the Trump team believes it can convince the Pakistanis to better cooperate with the United States in terms of clamping down on terrorist groups who are using their territory as sanctuary, in particular the Haqqani Network, which is a component of the Taliban and has carried out many of the most lethal terrorist attacks in the Afghan capital, Kabul. However, the Obama administration also tried to get the Pakistanis to rein in the Haqqani Network, to little avail.
Third, successes on the battlefield against the Taliban may get them to the negotiating table, as a negotiated settlement is the only way to end the war.
Fourth, the Afghan National Army is a more professional military force than it was several years ago.
Haqqani Network and Pakistan
A key element in all this is Pakistan, which "does have influence over the Haqqani leadership," according the US official.
This is particularly important because the leader of the Haqqanis
, Siraj Haqqani, is now the deputy leader of the Taliban and also runs its military operations
An important factor in the strategic planning is that five Americans are being held hostage
by the Haqqanis, including Caitlan Coleman and her two children under the age of 4 who were both born in captivity, as well as Kevin King, a teacher at the American University of Afghanistan in Kabul and author Paul Overby.
In addition, Canadian Joshua Boyle, the husband of Coleman and another American University of Afghanistan teacher, Timothy Weeks, an Australian citizen, also are being held by the Haqqanis.
According to the US official, the plight of the American hostages is "constantly discussed" with the Pakistanis and is raised "at the most senior levels."
If the Pakistanis don't do more to clamp down on the Haqqanis, the Trump administration could authorize additional drone strikes and also make public information about the links between them and the Pakistani military intelligence agency ISI, according to the US official.
There are risks, however, in amping up pressure on the Pakistanis, who have been told to "do more" about terrorist groups on their territory by successive American administrations over the past decade and a half.
The Pakistanis feel that they have already done quite enough. The India-based South Asia Terrorism Portal estimates that more than 6,700 Pakistani soldiers have died fighting the Taliban and over 21,000 Pakistani civilians have been killed in terrorist attacks
over the past 14 years. Other estimates run even higher.
The Pakistanis also have important cards of their own to play if the Trump administration does amp up pressure on them -- which is the fact that Afghanistan is a landlocked country and the easiest air and land routes into Afghanistan to resupply US soldiers are thorough Pakistan. Pakistan could make the flow of American supplies into Afghanistan more difficult in a number of different ways.
It's a dilemma that the George W. Bush and Obama administration faced, which is that the United States needs the help of the Pakistanis in a number of ways and can only cajole or coerce them so far.
The Pakistanis are also closely allied to the Chinese, who are providing them with tens of billions of dollars of investments. It wouldn't be smart to push them further into the arms of the United States' nearest peer competitor, China.
The Trump administration has the benefit with the Pakistanis of being a newly installed administration, which gives them leverage, but the issue of how best to deal with Pakistan and the search for the optimal approach in Afghanistan has bedeviled three successive American administrations since 9/11.
The most promising approach in the Trump administration strategy is its long-term commitment to Afghanistan. As the Trump administration formulates its South Asia strategy and the public messaging around it, this is the key point that needs to be emphasized.