Since Gaddafi's ousting in 2011, Libya has been in turmoil. Several insurgency militias still seek power in the rich oil-country.
NATO's intervention in Libya became stigmatised as the "worst mistake" of the former US administration, after Obama made his renowned comment during a Fox News interview and conceded he regretted: "…failing to plan for the day after, what I think was the right thing to do, in intervening in Libya".
The confession did not seem to have much effect on American policy in the region, however, as it continued to allow Russian influence to grow and perhaps pave the way for more benefits under a Trump administration.
In 2016, two major powers emerged in Eastern and Western Libya, respectively. The Government of National Accord (GNA) in the West, is recognised by the UN. In the East, the Libyan National Army, under the leadership of the secular commander Haftar, has been promoting an anti-jihadi strategy and openly courting Russia.
Russian commanders have received Haftar multiple times in the past two years, while he seeks military support to expand his control towards Western Libya.
It has taken Russia a long time to explicitly declare its position on the Libyan political landscape. As Russia shows itself to be more and more open to the candidacy of Haftar, other geopolitical developments strengthen their approach, perhaps ultimately providing an opportunity for a great deal of influence in a failed state on Europe’s doorstep.
"Russia still technically supports the UN peace process and the Libya Political Agreement, and as Haftar has consistently refused to compromise or participate in negotiations, it was politically tricky for Russia to declare its support for Haftar openly," said Rhiannon Smith, the managing director of Libya Analysis.
"Global political dynamics are shifting; with the Trump administration in power, the UN peace process is crumbling, and there are indications that several European nations are beginning to engage with Haftar. So Russia feels it can confidently back Haftar without repercussions in order to strengthen its influence in Libya and the wider MENA region."
This scenario has muddied the already murky Libyan waters.
Egypt and Russia are lying in wait, with fingers crossed that the UN will lift sanctions, and that Trump will let arms into Libya. Trump has so far signed executive orders at an extraordinary rate, 20 times faster than his predecessor. This attitude to governance opens up the possibility that the Republican-dominated US government could allow Egypt and Russia to provide intensive military assistance to Haftar.
"If Trump were convinced to support Haftar, or at least to let Egypt and Russia support Haftar in Libya, then the arms embargo may be lifted and decisive external military support given to Haftar, who would then essentially act as a Russian puppet in the southern Mediterranean," said Smith.
Habibulah Mohamed Lamin is a journalist based in the Western Sahara refugee camps in Tindouf, Algeria. He has worked as a translator and is director of Equipe Media Branch, a group of media activists covering Western Sahara. His work focuses on politics and culture of the Maghreb.
Follow him on Twitter: @habibullahWS