MLA and MP, 1977–1993

Singh was president of the Raghogarh Nagar palika (a municipal committee) between 1969 and 1971.^[6] An offer in 1970 from Vijayaraje Scindia for him to join the Jana Sangh was not taken up and he subsequently joined the Congress party.^[25] He became a Member of the Legislative Assembly (MLA) as the party's representative for the Raghogarh Vidhan Sabha constituency of the Madhya Pradesh Legislative Assembly in the 1977 elections.^[26] This was the same constituency that his father had won in 1951 as member of the Legislative Assembly (MLA) as independent candidate for the Raghogarh Vidhan Sabha constituency following the 1951 elections.^[11] Digvijaya was later re-elected from the Raghogarh constituency and became a Minister of State and later a Cabinet Minister in the Madhya Pradesh state government led by Arjun Singh, whom he has called his mentor,^[27] between 1980 and 1984.^[28]

He was president of the Madhya Pradesh Congress Committee between 1985 and 1988, having been nominated by Rajiv Gandhi, and was re-elected in 1992.^[13] He had been elected as a member of the 8th Lok Sabha, the lower house of the Parliament of India, in the Indian general election of 1984, representing the Rajgarh Lok Sabha constituency. He was the first Congress politician to win the constituency, which had been created in 1977. Having won that contest by 150,000 votes, he lost the seat to Pyarelal Khandelwal of the Bharatiya Janata Party (BJP) by 57,000 votes in the 1989 general election. He regained it in 1991, becoming a member of the 10th Lok Sabha.^[29]

Chief Minister, 1993–2003

In 1993, he resigned from the Lok Sabha because he had been appointed Chief Minister of Madhya Pradesh. His brother, Lakshman Singh, had been elected in 1993 as a Congress MLA in Madhya Pradesh from the same Raghogarh assembly constituency that Digivijaya had previously held. Lakshman resigned from the seat in favour of Digvijaya, who needed to be elected to the Madhya Pradesh Legislative Assembly in order to fulfill his role as Chief Minister. However, the scheme failed when a petition was filed that challenged the validity of Lakshman's 1993 election. Digvijaya instead won the by-election from Chachoura constituency, which was vacated by the Former MLA Shivnarayan Meena that time for the purpose.^[29] The Hindi Belt, of which Madhya Pradesh is a part, has a significant number of economically and socially disadvantaged Dalit and tribal communities. Through his policies, which have evoked both strong support and criticism among academics, Singh targeted the prospects of those people during his first term in office. These efforts attempted to arrest the declining support for the INC by those communities, who since the 1960s had increasingly been favouring the Bahujan Samaj Party (BSP), the Jana Sangh and its political successor, the BJP. He followed the example set by Arjun Singh in taking this approach, which was not adopted in other areas of the Belt such as Bihar and Uttar Pradesh. Sudha Pai says, "He was driven by both the political imperative to sustain the base of the party among these social groups and ... a commitment to improving their socio-economic position." The "Dalit Agenda" that resulted from the Bhopal Conference in 2002 epitomised the strategy, which by Digvijaya Singh's time was more necessary than during Arjun Singh's period in power because one outcome of the Mandal Commission had been increased Dalit desires for self-assertion. His approach to reform in what was still largely a feudal society was driven by a top-down strategy to achieve Dalit and Tribal support, as opposed to the bottom-up strategy of other belt leaders such as Mayawati , who lacked Singh's upper caste/class status and harnessed the desire for empowerment in the depressed communities through identity politics. Among the measures introduced to achieve his aim were the Education Guarantee Scheme (EGS), redistribution of common grazing land (charnoi) to landless dalits and tribals, free electricity for farmers, the promotion of Panchayati Raj as a means of delegating power to villagers and a supplier diversity scheme which guaranteed that thirty per cent of government supplies would be purchased from the disadvantaged groups. There was less emphasis than previously on methods of assistance that were focused on reservation of jobs.^{[30][31][lower-alpha 1]}

The Chief Minister of Madhya Pradesh, Shri Digvijay Singh calling on the President of India, Dr. Shankar Dayal Sharma, at Rashtrapati Bhavan, in New Delhi on 5 May 1997

Returning to the Raghogarh constituency for the 1998 elections,^[33] Singh was re-elected and appointed by Sonia Gandhi to serve a second term as chief minister.^[34] Census data suggests that Singh's education reforms had become a particularly successful aspect of his government. Those reforms included the construction of thousands of new village schools under the EGS, and may have been significant in increasing the literacy rate in Madhya Pradesh from 45 per cent in 1991 to 64 per cent in 2001. The improvement among girls was particularly high, growing from 29 per cent to 50 per cent.^{[35][lower-alpha 2]} In his second term as Chief Minister, Singh sought to extend his decentralising, socially beneficial ideas by instituting reforms in healthcare that would guarantee a minimum level of care at panchayat level by financing the training of locally nominated healthcare professionals. This mirrored his earlier efforts in education and was known as the Healthcare Guarantee Scheme.^[37]

Chhattisgarh gained administrative independence from Madhya Pradesh in 2001 under the terms of the Madhya Pradesh Reorganisation Act.^[38] Singh was directed by Sonia Gandhi to ensure the selection of Ajit Jogi as the Chief Minister for the new state and this Singh did, although Jogi had been critical of his style of politics and Singh had personally preferred not to see him installed to that office. While Singh managed to convince the majority of Congress Legislator Party members to back Ajit Jogi, the absence of Vidya Charan Shukla and his supporters at the meeting raised questions about the exercise of seeking consensus because Shukla was the other main contender for the post.^[39] Subsequently, Singh met with Shukla in order to allay concerns.^[40][41]

Singh won the Raghogarh constituency again in 2003^[42] but his party overall was heavily defeated by the BJP, as it also was in Rajasthan and Chhattisgarh.^[43] The defeat in Madhya Pradesh has been attributed in large part to deadlocks in the pursuit of development that had arisen as the Panchayati Raj and central government squabbled about the extent of their respective powers, and to frequent electrical power cuts. The latter resulted from thirty-two per cent of what had been the generation capacity of Madhya Pradesh now being in the new state of Chhattisgarh: while Chhattisgarh did not need all of that capacity, much of it had historically been used in the remainder of Madhya Pradesh, which now found itself having only around 50 per cent of the power that it required. Aditi Phadnis, a political journalist and author, also notes that in 1985, the state had been producing a surplus of electricity through a process of technical and administrative efficiency that was the envy of other areas and that then "The State Electricity Board began to be looked upon as a milch cow by successive politicians, Digvijay Singh included." Power was given away and no money was set aside for repairs and maintenance.^[31] One of Singh's last proposals while in office was to write-off the electricity bills of 1.2 million people over the preceding three years. In this, he was thwarted by the Election Commission of India, which ruled the proposal to be a breach of election rules.^[44] Singh had claimed that it was desirable because the farmers of the state — who needed electricity to power water pumps^[36] — had suffered three years of drought conditions.^[45]

C.M. Digvijaya Singh with Pandit Ram Kishore Shukla, Santosh Kumar Shukla, Surendra Shukla and Lal Bahadur Singh (extreme left) at chief minister house, Shyamla hills Bhopal in 2002.

Work at national level

Following his party's defeat, Singh determined that he would not contest any polls for the next decade and the Raghogarh constituency was won by his cousin, Mool Singh, at the next elections in 2008.^[27] Singh shifted his attention to working for Congress from the centre, becoming a general secretary of the AICC and being involved in the party's organisation across several states, including Andhra Pradesh, Assam, Bihar and Uttar Pradesh.^[27] In 2012, Singh said that there was a need for younger people to be involved in state assemblies and that he had no further interest in contesting state elections. He expressed a willingness to contest the 2014 Lok Sabha elections if Congress wanted him to do so; he also said that he would like to see his son as the incumbent of the Raghogarh constituency.^[27][46] His son, Jaivardhan, was accompanied by his father when he joined the INC in June 2013 after previous involvement in its youth section. Mool Singh, the incumbent MLA, announced then that he would not be contesting his Raghogarh Assembly seat in the forthcoming elections, paving the way for Jaivardhan to be elected in a form of dynastic succession that is a feature of politics in India.^[47]

In January 2014, he was elected as a member of parliament to the Rajya Sabha from Madhya Pradesh.^[48]

Singh has been criticised by his opposition for corruption,^[49] which he denied.^[50] In 2011, a charge sheet was submitted in court against him^[51] but the Central Bureau of Investigation (CBI) determined in March 2014 that there was no case to answer.^[52]

In June 2015, Singh petitioned the Supreme Court, pleading for a CBI probe into the Vyapam scam. He claimed to have interacted with a whistleblower who had revealed sensitive information to him.^[53] The CBI dismissed the claim in November 2017, raising the possibility that Singh could be prosecuted for fabricating evidence.^[54]

In the 2019 Indian general election, he ran for Lok Sabha in the constituency of Bhopal, but lost to Pragya Singh Thakur.^[55]