Five-time Tamil Nadu chief minister and Dravida Munnetra Kazhagam (DMK) president Muthuvel Karunanidhi passed away on Tuesday (7 August), following a brief battle with urinary tract infection . He was 94 years old.

While his long political career saw many successes, there were undoubtedly some moments he would have wanted to forget.

Here are the 10 key moments:

1. In the 2016 Tamil Nadu state elections, DMK lost many seats by a close margin. The party allowed its coalition partner Congress take on All India Anna Dravida Munnetra Kazhagam (AIADMK) in 41 constituencies. AIADMK convincingly won this duel, with the Congress winning just eight seats. DMK, on the other hand, won most of the seats it contested against AIADMK. It also failed to check the latter from bribing voters.
2. DMK chose to go it alone in the 2014 Lok Sabha polls. It resulted in the party not winning a single seat in either Tamil Nadu or Puducherry. Ironically, an alliance with Congress and other like-minded parties could have helped.
3. In the 2011 state assembly elections, DMK and AIADMK had announced a slew of freebies to voters if they came to power. But the AIADMK, wise from losing the 2006 elections when the DMK promised colour television sets, came up with a better plan. For example, when the DMK promised either a grinder or a mixer, the AIADMK promised both. The DMK promised laptops for college students but the AIADMK also promised laptops for higher secondary students.
4. On 22 March 1989, the late Jayalalithaa objected to Karunanidhi presenting the state budget, and called him a “criminal”. Incensed over this remark, Karunanidhi covered his mike and made a personal remark against her. It led to a brawl which led to Jayalalithaa’s sari being torn. She came out of the assembly crying, and alleged that attempts were made to disrobe her.
5. The 1991 assembly elections that saw DMK being reduced to just two members in the house. Karunanidhi himself won by a meagre 890 votes from Madras Harbour constituency. He resigned from the seat, which was dubbed by his critics as an inability to face a house that was filled by the AIADMK and its coalition partner, the Congress party.
6. After DMK lost the 2001state polls, Karuananidhi’s attendance in the assembly was poor. Often, he would sign the register in the Speaker’s chamber and walk off. From 2011 till his death, the former chief minister’s attendance in the assembly was very low even though he continued drawing salary and perks. His critics claimed that him merely appearing to mark his attendance was an effort to scuttle any attempts by the AIADMK government to arrest him.
7. During the 1984 Tamil Nadu elections, Karunanidhi openly asked the people, “Isn’t it enough you have punished me so long?”. He also told the crowd that if they elected him, he would administer until the return of incumbent chief minister and AIADMK leader M G Ramachandran, who was hospitalised in the US. That election was won by the AIADMK.
8. In 1979, the DMK indulged in violent protests against the visit of former prime minister Indira Gandhi to Tamil Nadu. Stones were pelted, which resulted in her being injured. Her sari was stained with blood but Karunanidhi made an atrocious remark, linking it to her menstrual cycle. A year later, he struck a deal with her and formed a coalition to fight the Lok Sabha elections. Congress and DMK won 37 of the 39 seats. Once Gandhi was in power, Karunanidhi got the MGR government in Tamil Nadu dismissed. He had also struck the deal to get him off the Sarkaria Commission enquiry into the alleged misdeeds during his regime between 1969-1976.
9. Between 1970-75, there were moments when Karunanidhi was snubbed by Indira Gandhi or forced to concede on the sharing of Cauvery river water. In December 1970, when he wrote to Gandhi seeking the setting up of a tribunal to settle problems between Tamil Nadu and Karnataka, she shot back saying that she wouldn’t do anything before the Lok Sabha elections in March 1971. Subsequently in 1975, when the Gandhi government tried to find a solution, then Water Resources minister Jagjivan Ram forced Karunanidhi to sacrifice 100 thousand million cubic feet of water from Tamil Nadu’s share. Initially, Karunanidhi had offered to give up claim on 60-70 TMC feet of water but Jagjivan Ram prevailed over him.
10. Often Karunanidhi had remarked that the DMK was not a “Sankara Mutt”, meaning decisions were taken in a democratic fashion in his party. But the DMK now sees family rule. Besides, second or third generation of select senior leaders, families continue to enjoy clout within the party, while workers have remained just foot soldiers.