Joseph Vissarionovich Stalin (1878-1953)
Pictured here in 1932 with Anastas Mikoyan (left) and Sergey Kirov (center). Mikoyan had a long career in Soviet politics and lived to the ripe old age of 83 before dying in 1978. Kirov was not so lucky. Although a loyal supporter of Stalin, he eventually came to be more popular than Uncle Joe, and about two years after this picture was taken, Stalin had him...(ahem)..."purged."
In this photo Stalin smokes his pipe in the background while poring over numerous documents, probably lists of people who were "next." In the foreground is Lavrenty Beria, one of the primary executors (no pun intended--well maybe a little) of the Great Purge, happily bouncing Stalin's daughter Svetlana on his knee.
As far as his pipe-smoking habits, well, I have read some about this, but I have no way to verify what I have read. Most of it is bad, which may be just because Stalin is so generally disliked. So with that caveat, this is what I have read.
Stalin allegedly never cleaned his pipes. Any respectable pipe smoker will tell you that this is bad. The frequency of cleaning varies from person to person, and often from pipe to pipe, but every pipe must be cleaned periodically. It may involve some minor reaming to remove excess cake, but often all that is required is that a pipe cleaner be moistened with a bit of cleaning fluid--which can be some expensive "real" pipe cleaning fluid or any liquid high in alcohol. I assume Stalin had plenty of vodka at his disposal; it would have made an excellent pipe cleaning fluid (I prefer Everclear, myself). The moistened pipe cleaner is run through the stem once or twice, followed by a dry cleaner. The same moistened cleaner (or a new one, if you prefer) is then inserted into the shank of the bowl and scrubbed in and out several times, followed by another dry cleaner. Then you put the pipe up for a day and let it rest. That's all there is to it, but apparently this was too much trouble for Uncle Joe. He was reported to have the foulest smelling cloud of mundungus around him when he lit his pipe, because he never bothered to clean them.
Item two on the list, which may be related to the previous item, is that he liked to smoke Dunhill's Royal Yacht. RY is a famous, or infamous, blend of various Virginias, but with a "unique flavor" added. It is this "unique flavor" which some find horrendously offensive, but others enjoy. I guess RY is about as controversial as a pipe tobacco can get. For an idea of what I'm talking about, you can check the Royal Yacht reviews at tobaccoreviews.com. I have never tried it myself, so I can't comment on it personally. One thing I can say for certain: tobaccos with flavor added (known as "aromatics") are about a million times worse at gunking up a pipe than natural, non-flavored tobaccos. This means your pipes will require even more frequent cleaning than if you only smoked natural tobaccos.