The 1992 presidential election was historic as the first one held after Estonia restored its independence, and it uniquely allowed the public to vote directly in the first round.

"I was just a diligent student at the University of Tartu," recalled Anvelt, now a senior editor at Delfi. "That was the only time there was a popular vote, and I was one of Lennart Meri's supporters."

Both Sildam and Anvelt acknowledged that Meri was a true superstar whom everyone looked up to.

"He was a real superhero — basically a super mouse — with incredible work capacity, traveling from country to country seeking support for Estonia," Anvelt said. "He was an excellent speaker and very skilled with languages."

However, Sildam pointed out that Arnold Rüütel was the initial favorite in 1992. "In terms of the popular vote, he was actually ahead," Sildam noted. "In the end, it was the parliament's decision that made Meri president."

In 1996, the old rivals Meri and Rüütel faced off in parliament again, but neither secured enough support, moving the presidential race to the electoral college for the first time.

Anvelt recalled a growing perception that Meri could not gather enough political support due to his strong personality. Sildam, however, believed it was entirely logical for Estonia to reelect Meri in 1996.

"There were many unfinished matters — major foreign policy issues and Estonia's shift from East to West," Sildam said. "Lennart clearly embodied the West."

Ultimately, Meri won the second round of the electoral college by a large margin and ceremonially began his second term at the Estonia Concert Hall.

After the turn of the millennium, the president was again chosen in the second round of the electoral college. Interestingly, the candidates put forward there — Toomas Savi and Rüütel — had not even run in parliament. Rüütel was eventually elected president by the electoral college.

In 2006, the process began again in parliament, where Toomas Hendrik Ilves was nominated in the second and third rounds, receiving 64 votes each time — just four votes short of the required majority. The decision moved to the electoral college, where Ilves faced Rüütel.

"I was an absolute fan of Ilves and was rooting for him," Anvelt said. "When the votes were counted, it was incredibly close. In the end, I think only 12 votes separated them."

Anvelt added that she was very happy Ilves won, calling him one of the best presidents Estonia has ever had.

Sildam recalled shaking hands with Ilves at the Estonia Concert Hall to congratulate him before returning to the Postimees newsroom to write a story. Shortly afterward, Ilves invited him to join the presidential office.

"At one point he called and I said no — I was working at Postimees and was very happy," Sildam admitted. "Then he called a third time, and a weak person gives in. It is very hard to say no to a president." Sildam went on to serve as the press adviser to Ilves for the next 10 years.

The 2011 election went down in history as the shortest, as Ilves was reelected in the first round of parliamentary voting with 73 votes.

Anvelt described the 2016 presidential election as a dramatic spectacle she likened to a show called "Estonia Searches for a Super President."

"It was a real tour of presidential candidates, full of drama — I would say even tears — and enormous disappointment," Anvelt said.

The candidates included Allar Jõks, Eiki Nestor, Siim Kallas, Mailis Reps, Mart Helme, and Marina Kaljurand. For the first time, the search for a president failed even in the electoral college.

Anvelt recalled that several candidates were deeply disappointed because they assumed the path to the presidential palace in Kadriorg was practically guaranteed.

"I am thinking primarily of Kaljurand and Kallas," Anvelt said. "I did not consider the others as strong favorites. Kaljurand had tremendous public support."

The election returned to parliament. Sildam remembered discussions in Kadriorg about what would happen if parliament also failed and the process went back to the electoral college. Politicians ultimately pulled themselves together, electing dark horse candidate Kersti Kaljulaid — whom most people had not heard of at the time — with a record 81 votes.

From the 2021 presidential election, Sildam most vividly recalls an interview with scientist Tarmo Soomere, then president of the Estonian Academy of Sciences. At the end of a Vikerraadio interview, Sildam casually asked whether Soomere would be willing to run for president if politicians asked him. Soomere sighed and replied, "Yes."

"That was one of those moments where the table seems to slide away and the chair collapses," Sildam recalled. "The journalist thinks, 'What do I do now?' because you are completely sure he will say something like, 'I don't know, there is still half a year to go.'"

Later it emerged that Soomere did not appeal to politicians, who turned instead to Alar Karis.

However, the election of Karis was not just a formality, as he did not receive enough votes in the first round in parliament. Some politicians appeared to test his nerves, but he was elected the next day with 72 votes, becoming Estonia's sixth president — a former rector of the University of Tartu and auditor general.

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