With his worst-ever electoral defeat in Andhra Pradesh and losing relevance in national politics, Nara Chandrababu Naidu is facing the biggest challenge of his career.

A leader, whose four-decade-long career saw his political pendulum swinging wildly from left to the right, the Telugu Desam Party (TDP) chief last year exercised even his last option -- aligning with the Congress. But this time, he ran out of both the options and the luck.

Till a day before the counting, Naidu was holding a series of meetings with leaders of various regional parties, desperate to cobble together an anti-BJP alliance to remain relevant in the national politics.

He wanted to stop his friend-turned-rival Narendra Modi from returning to power even as he was facing an acid test at home against Y.S. Jagan Mohan Reddy.

At the Centre, the 69-year-old wanted to achieve what he did in 1996, when as the convenor of the United Front (UF) he brought together regional parties to prop up government of the third alternative. In 1999, he donned a similar role for the BJP-led National Democratic Alliance (NDA).

Many saw in him a shrewd politician and few branded him a rank opportunist as he aligned with the BJP, apparently to ride on the Vajpayee wave. He succeeded in retaining power, which he got in 1995 after leading a revolt against his father-in-law and TDP founder N.T. Rama Rao.

Then known as the poster boy of new economic reforms, a reformist and a tech-savvy leader, Naidu mastered the skills of doing business with any formation at the Centre, irrespective of its ideology.

After losing power to his bete noire Y.S. Rajasekhara Reddy (YSR) in 2004 following a record 9-year stint as Andhra Pradesh chief minister, Naidu admitted his priorities were lop-sided which led to the neglect of agriculture in the state.

So he promised a slew of freebies in the 2009 elections, but the people remained unconvinced and gave YSR a fresh mandate.

The emergence of Narendra Modi as the prime ministerial candidate in 2014 offered Naidu a chance to revive his political fortunes.

He not only joined the NDA once again but by campaigning with Modi, he succeeded in storming to power in the truncated state of Andhra Pradesh, as people preferred him, apparently for his experience in developing Hyderabad as a tech hub.

As a leader who always enjoyed the role of a kingmaker and extracted his pound of flesh from the government at the Centre, Naidu was uncomfortable in the new dispensation where Modi had absolute majority.

Though facing post-bifurcation challenges like lack of state capital and poor finances, he had no option, but to quietly accept whatever was doled out to the state.

However, it was when YSR's son and the chief of the YSRCP Y.S. Jagan Mohan Reddy started targeting him for his compromise over the Special Category Status (SCS) that Naidu realised how he was losing the ground to the opposition. Last year, he pulled out of NDA government accusing Modi of 'betrayal'. BUt the opposition still remained aggressive in exposing his flip-flops over the SCS.

From a great admirer of Modi, Naidu soon turned into his worst critic and even joined hands with the Congress, his party's sworn enemy of 35 years. This was Naidu's biggest political misadventure and his rivals targeted him incessantly for his opportunism.

He even joined hands with the Congress in the Telangana Assembly elections, but the experiment ended in a disaster with the Congress-led United People's Alliance (UPA) biting the dust.

The flip-flops continued as he decided not to have an alliance with the Congress in Andhra Pradesh thereafter, even as he continued his efforts for an anti-BJP front at the Centre led by the Congress.

"He was shifting goal-posts time and again on various issues. The opposition played it in a big way and voters were also watching all this," said political analyst Palwai Raghavendra Reddy.

The YSR Congress Party (YSRCP) chief's 'padyatra' and his party's aggressive campaign promising a wide range of freebies also rattled Naidu. His announcements of welfare schemes and even the implementation of some of them were too late to convince the voters.

The allegations of corruption, casteism also dented Naidu's image and ultimately led to his worst-ever poll performance winning just three Lok Sabha seats..

A second term for Modi with a massive majority also dashed Naidu's hopes of salvaging some pride with a role at the Centre.

With his son Nara Lokesh suffering defeat, Naidu's dream of grooming him as his political successor was also shattered.

"Naidu is already 69, and he may not find himself in the same physical and mental shape to lead the party campaign five years later," said Raghavendra Reddy.