A Century of Chess: Harry Pillsbury (1900-1906)
Drawing of St Petersburg 1895/96

A Century of Chess: Harry Pillsbury (1900-1906)

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The story of Pillsbury is that he caught syphilis from a St Petersburg prostitute during the 1895/6 quadrangular event and was never the same after that. The reality is that he was the world’s #2 (or maybe #3) for nearly a decade afterwards and put in world class performances until a year or two before his death.

I think it’s been a bit lost in chess history just how beloved Pillsbury really was. He was popular, charismatic, ever-gracious, the matinee idol of how a chessplayer should be. Had he lived - and had he not been just a shade inferior to Lasker in chess ability - then it’s possible to imagine a world champion who would have been an international icon and a great popularizer of chess, somebody who would have made chess seem athletic and cool. (Although, come to think of it, Capablanca was exactly that sort of world champion a few years later and chess nonetheless never lost its bookish reputation. But Pillsbury would have made an even more charming and extroverted champion, and my feeling is that something incalculable was lost in his non-ascension to the title.) As it played out, he became a very similar figure to Paul Keres and Levon Aronian, ‘crown princes’ of chess, popular favorites, who for one reason or another - bad luck or a lack of soundness somewhere deep in their play - couldn’t reach the very top.

"Who you calling a chess nerd?"

Pillsbury had come out of complete obscurity to win the Hastings 1895 tournament - by far the greatest tournament held up till that time. (Actually - and this picturesque fact has been oddly buried in chess history - he had spent two years as the operator of Ajeeb, the chess machine, an experience that must have been invaluable for him, allowing him to play constantly and to be, in effect, one of the world’s very few chess professionals, although without anyone’s knowing it.) The victory at Hastings automatically made Pillsbury a contender for the world championship, and he very nearly cemented a match by playing brilliantly in the first half at St Petersburg 1895/96. But he collapsed in the last three cycles and finished with a minus score. He lost a playoff to Tarrasch at the marathon Vienna tournament of 1898 and finished distant second to Lasker at both London 1899 and Paris 1900 and that’s kind of where the chess world loses track of Pillsbury - very great but not quite great enough.

Ian Richardson in the role of Harry Pillsbury

In reality, though, Pillsbury entered the new century with a very good claim as the worthiest world challenger and secured that with a long string of second place finishes - second at Vienna, at London, at Paris, at Munich 1900, at Monte Carlo 1902, at Hanover 1902, and then finally third at Monte Carlo 1903. As ever, the chess world tended to fixate on first prizes, but Pillsbury’s was a remarkable record - reminiscent of Keres’ four second place finishes in Candidates Tournaments - and it’s a mystery to me why there wasn’t more of an effort around 1900 to arrange a match between him and Lasker.

Around 1904, though, Pillsbury's play abruptly declined along with his mental health - a suicide attempt in 1905, clearly instigated by insanity, became a surprisingly widely-circulated news story. It’s heartbreaking to play over his games from 1904, knowing as he himself knew but almost no one else did, that he was likely to die soon and that, until he did, his mental powers would steadily collapse. As Frank Marshall observed of this period, "His originality went first, then his opening play, afterwards his combinative power, and finally his endgame play. That stayed with him the longest." 

Pillsbury in the role of Harry Houdini

Maybe most heartbreaking of all is his Pickett’s Charge of a game against Lasker at Cambridge Springs. That was Pillsbury’s first bad tournament - finishing shared eighth - but he used the opportunity to spring on Lasker an opening innovation that he’d been developing since 1896 and which he had undoubtedly been saving for a world championship match that he now knew would never take place.

Pillsbury's legacy - I believe - has been a bit of a casualty of his sudden demise. Syphilis was a shameful illness, as (from the perspective of the chess community) was the initial cover story that he had lost his mind through chess - "the tremendous mental strain which the masters undergo in the great tournaments is too much for the human brain," wrote The Washington Times - as was the corollary story that his bohemian lifestyle had ruined his health (the British Chess Magazine claimed that "the cause of his breakdown was irregularity in time of eating and sleeping and the neglect of outdoor exercise" - and Alekhine would write that he "aspired for the candle of his life to burn constantly at both ends").

Washington Times. 1905.

In some sense, the chess community had to go into spin mode - it was less-than-great that three of its most famous champions, Morphy, Steinitz, and Pillsbury had all cracked up - and Pillsbury came to be viewed as something of a freak, the player with the eidetic memory and the lack of self-control. (His memory was really remarkable - he could, for instance, play 16 blindfold games of chess, 8 blindfold games of checkers, and a hand of duplicate whist at the same time and could recite word-for-word, backwards, a paragraph of an article that had just been read to him.)

Los Angeles Herald 1898

I find the diminishing of his reputation to be really unfortunate - his name is rarely brought up, for instance, in lists of best-players-never-to-have-been-world-champion - and his games and his sayings are less central to chess history than they should be. I like his ringing praise of chess: "There is nothing nobler or more intellectual in sport than chess. It calls out qualities of character – of the heart as well as the head. I have often wondered why chess is not taught in the schools. It brings about concentration of thought upon a given subject as no other study I know of." And I like his paean to concentration: "Perhaps the mental quality most useful to the chessplayer who wishes to rise to distinction in the game is concentration – the ability to isolate himself from the whole world and live for the events of the board while a match is proceeding. And yet 'concentration' does not quite suit me as expressing the quality I refer to, for concentration implies narrowing, and I am satisfied that the influence of chess broadens the mind." 

Womanhood. 1903.

Best of all are his sportsman's line before Hastings 1895, "I want to be quiet, I mean to win this tournament," and his gnomic summation of the game, "Chess is what you see" - which I'm not sure I completely understand but is somehow perfect.  

Pillsbury's Style

1. Energy

Pillsbury's play really is incredibly similar to Keres and Aronian’s and seems to be made of very light, delicate materials. There's the sense of a dance in which the tempo steadily, relentlessly increases, with Pillsbury somehow keeping his composure and his opponent eventually faltering. And the sense too that he had a basically genial attitude towards his opponent - it's like Aronian saying that 'chess is a conversation' and Spassky noting that Keres always had to be friendly terms with his opponents. The idea isn't to create some complex strategic masterpiece or to 'dominate' the board - as Tarrasch wrote of Pillsbury, "Scientific profundity was alien to him." Everything is in the realm of dynamics, tactics, the initiative - there's a fair fight but Pillsbury is almost always bolder and more resourceful. 

2. Offsides

Central to Pillsbury’s approach was the tendency to launch an attack before either player was ready for it - getting in an early strike and then using his ingenuity to bring up his reserves in time. This style reminds me of a football striker who specializes in taking a long ball down the side of the pitch and has the timing to just barely stay onsides. That kind of exquisite timing left little room for missteps, and Pillsbury’s two critical losses of this period - at London 1900 against Lasker and at Monte Carlo 1903 against Tarrasch - were cases of Pillsbury pushing too soon out of the opening and a shrewd opponent keeping him honest about it. The other way to describe this is that Pillsbury was really a pioneer in the art of the initiative - he wasn't particularly impressed with the precepts of classical strategy or the inherent materialism of the 'modern school' and was willing to accept all sorts of deficits for the ability to strike first. Fascinatingly, Pillsbury ascribed his success at Hastings to "certain new theories which I had evolved about the game." He doesn't go on to explain what those theories were, but, based on his play, one would tend to assume that they were along the lines of developing a stable classically-approved opening position and then bidding for the initiative as soon as possible. Lasker had something similar in mind when, in his obituary for Pillsbury, he wrote that, while the modern school was systematically 'weeding out' and dismantling the older Romantic ideas, Pillsbury, "with great courage undertook the work of rehabilitation" - finding the razor's-edge balance between initiative and solidity that would characterize the next phase of chess evolution. Viewed in this way, Pillsbury becomes something like a 'giant of power play' (in Neil McDonald's phrasing) or 'the architect of modern chess' (as Daniel Naroditsky describes him) - fully aware of all of the elements of the post-war Soviet school but straining to incorporate them into the somewhat more sedate openings of the classical era. 

3. Endgame dynamism 

Pillsbury had a remarkable ability to extend the initiative into the endgame. As Tarrasch writes, this skill "instilled fear in the hearts of even his strongest opponents." It came from the evident conviction that chess was nothing but kinetic energy - that whichever side was passive was probably losing and that dynamic chances could be found in virtually any position. 

Pillsbury in the Opening

Pillsbury claimed, in 1901, that "in modern practice among the great masters only two openings – the Ruy Lopez and the Queen’s Pawn – are considered to retain the advantage of the first move for any length of time." Given the time that he was playing in, he was able to achieve extraordinary, and almost effortless results, by playing the white side of the Queen's Gambit Declined. With startling obstinacy, his opponents failed to realize that the Queen's Gambit really was an attacking opening - that if white obtained greater space and particularly if he brought his knight to e5 as in the Pillsbury Attack then black's kingside would prove almost impossible to defend. 

Pillsbury won so often and easily in the standard classical openings that his capacity to innovate can easily be overlooked. As black, he experimented with the Sicilian, Dutch, Petroff, Scandinavian - always with the idea of creating imbalances from the opening moves and avoiding the types of 'closed games' with which he was so dominant with the white pieces. Most dramatically, he fooled around with hypermodern ideas around 1900 and seemed to grasp the key concept that wouldn't enter into chess theory for another half-century, that the voluntary surrender of space could be accompanied by the storing of potential energy and that the more 'coiled' player could be the one controlling the game's dynamics. 

Sources: Not surprisingly, Edward Winter has a pair of terrific posts on Pillsbury (here and here) which includes a trove of Pillsbury photos. Encomiums to Pillsbury are include in Emanuel Lasker: A Readerthe British Chess Magazine 1906, Richard Réti's Masters of the Chessboardand sprinkled throughout Frank Marshall's writing

Plugs: As I mentioned last week, I've been working on a Substack called 'Castalia.' This is non-chess-related (if there really is such a thing). Posts are essays, short stories, commentary on politics and aesthetics, etc. The idea is that this will be a creative home for me - and primary means of expression for some time. Thank you for indulging me on this bit of cross-promotion!