Janek Mäggi: A President Should Paint Their Presidency!
09.10.2026
, Postimees
The finest presidential portrait is Kaido Ole’s painting of Toomas Hendrik Ilves.
Jüri Arrak’s portrait of President Meri was also strong; the others, less so.
Ülle Madise is advised to seek a second term so that a stronger portrait can emerge.
A photographer taking a president’s official portrait has a great advantage over the artist painting them: the photographer can capture hope, enthusiasm and the future, because the photograph is taken before the term begins — when everything still lies ahead. The painter must put the exhaustion, tedium and fatigue of the term into the picture, while still showing that the president’s legacy is magnificent and the mark they have left is unforgettably profound, writes Janek Mäggi, head of the advocacy agency Powerhouse.
Of the artists who have portrayed Estonia’s presidents to date, it must certainly be said that they are all accomplished and have hit the mark. Without wishing to spoil the mood, however, only a couple of the works have turned out exceptionally well.
The best, in my view, is Kaido Ole’s portrait of Toomas Hendrik Ilves, which would beat all the others hands down at auction. There is plenty of Kaido Ole in the picture, but not a millimetre less of Toomas Hendrik Ilves — a mischievous, self-assured, influential man who remains utterly sincere even when sincerity does not always work to his advantage. Another €100,000 might be fetched by Jüri Arrak’s Lennart Meri, which is not so very Arrak at all, but rather unmistakably-the-real-Lennart.
The market value of the other four works is rather low. The portraits of Konstantin Päts, Arnold Rüütel, Kersti Kaljulaid and Alar Karis are less valuable — all lack that real spark or a stroke markedly different from the master artist’s usual style: surprise, freshness, expressiveness, flair. They are too ordinary and perhaps, for that reason, rather lifeless.
In art, of course, who painted a work matters far more than what or whom it depicts. Presidential paintings are no exception.
As a seasoned art museum visitor, having probably visited more than 100 art museums around the world, I have noticed that the best portrait is one that makes you exclaim at first glance: “Hang on, what have we here!” In that sense, Kaido Ole has set the bar very high for this particular genre.
But Ole also had the most time to reflect on the president’s legacy, because apart from Lennart Meri, Toomas Hendrik Ilves has been the only president of modern Estonia to secure re-election. For a president, seeking re-election is not merely an opportunity but a moral duty — to show that choosing me was a sound decision, that I deserved it.
Tõnis Saadoja’s Alar Karis is recognisable and captures his character, but he looks slightly hunched and tired. A president cannot afford to grow tired, to go down in history looking weary. For the wall of Kadriorg Palace, he is perhaps too familiar, too casual, too much of a regular bloke.
Although it is fashionable nowadays for men in suits to attend the presidential reception wearing white trainers, I would have expected a clear choice: if white trainers, then go all in on white trainers, rather than a chummy dullness that disregards the office.
If all the presidential portraits were donated back to the Estonian Artists’ Association and put up for sale to plug financial gaps, each work would, of course, fetch a considerable sum. All are worth five figures, but only two are worth six.
With the term of the new president, Ülle Madise, about to begin, the paintings suggest some advice for her: work in a way that earns you a second term — then the artist will be better able to capture what you have achieved as president and put it into the picture; do not grow tired, lest the public get the impression that life in Kadriorg was like the television series Õnne 13: five years and not a single event; paint your own presidency in a way that makes it a joy for an artist to paint it too — add some colour, Madam President!
2591994
