And now, his induction as a Cabinet minister in the Modi government marks a rare happy turn in his long career where he was forced to live in the shadows of rival Jat leaders like Hooda and National Lok Dal's O P Chautala.
Singh took a big gamble before Haryana Assembly elections by ending his over four-decade association with Congress to join BJP and it paid off as the saffron party stormed to power in the state and his wife also got elected as an MLA.
Grandson of illustrious peasant leader Chhotu Ram, the 68-year-old politician has been a five-time MLA and served as a cabinet minister in Haryana three times.
As his differences with Hooda government grew, he was brought to Parliament as a Rajya Sabha MP in 2010 and was tipped to join the Manmohan Singh government but last minute political machinations tripped him. Though Congress tried to placate him by making him a permanent member of its highest decision-making body Congress Working Committee but he could never come to terms with the denial of a ministerial berth what he considered was his due.
The rise of BJP in Haryana offered him an alternative and his stature as a Jat leader also proved to be an asset for the saffron party. BJP believes Singh's entry in the government will bring Jats closer to it in a state where they are the most numerous and influential community.