In 2009, his candidature grabbed a lot of media attention. After all, the president's son was given a ticket and a senior Congress leader and minister, Dr Sunil Deshmukh, was uprooted to make way for him. This time around, Raosaheb Shekhawat, the son of former president Pratibha Patil, says it's very different.
"For once, there has been no media coverage this time from the national media. You are the first one," he said.
While Deshmukh continues to remain his rival, he is now contesting on a Bharatiya Janata Party (BJP) ticket. "I am glad he is not the President's son this time. The entire administration was put into action to ensure he wins," said Deshmukh.
While Shekhawat doesn't feel so, most of his workers admit that this is a tougher election than 2009. "Pratibha Patil is not the president anymore, we aren't in power at the Centre and we are very weak in the state too. These factors will play a major role," said a close Shekhawat aide.
On the streets of Amravati, the excitement is palpable as the showdown between the two reaches a climax. Both the contestants have had close ties with the city. Deshmukh was an MLA twice and had brought many good projects to the region during his tenure as the guardian minister. On the other hand, Shekhawat hails from a family which has been rewarded by the city with almost every important political post there could be.
Between Patil and her husband, Devisingh Shekhawat, they have been elected a corporator, a mayor, an MLA and an MP from the city. While neither of the two protagonists say it, amongst workers of both, it's clear: this fight is much more than an electoral battle.
For Deshmukh, it's a bid to avenge "the five long, productive years of my life I wasted," while for Shekhawat, it's a challenge to show he doesn't need his mother in the President's chair to win the contest. Does he feel bad, living in the shadow of his parents? Shekhawat answers, "I am a self-made man. I am fortunate to have my mother as the former President. He's not as fortunate. How can you blame that on me?"
Incidentally, Patil has been missing from her son's campaign this time around, preferring to spend time in her Pune home. Shekhawat said, "She's 80 and I don't want to trouble her."
On paper, Deshmukh seems confident of bagging the seat and looks stronger. But his switching loyalties may also have repercussions. Last time, when he lost by 5,000-odd votes, he bagged nearly 10,000 votes from the Muslim community.
He may not get those this time, many suggest. Secondly, the area has been a Congress stronghold, electing the BJP only twice since 1978. Deshmukh partly agrees but says, "Last time around, I had no symbol. This time, the BJP's voters along with my traditional supporters will stand behind me."
How does he explain changing loyalties? Apologetically, he says, "Till the last day, I was at the doorsteps of the Congress, asking them to give me a ticket. When they didn't, I had to take this decision, as it was a question of my political career."
Locals acknowledge Shekhawat's work, but credit much of it to Patil. Some others are in favour of Deshmukh, but the impact of his switch remains to be seen. On the ground, Amravati, it seems, is also looking to find answers to these questions.