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A chess game can be divided into three phases: opening, middlegame and endgame. Most of us are very aware of when an opening starts, or when the game has become a fairly simple endgame. What many people struggle with, is recognizing when a middlegame starts or finishes.

There are no strict rules to determine this. Generally, however, it is considered that a game has reached its middlegame phase once both sides have finished their development, castled, and connected their rooks. In practice, that is rarely so, and middlegames will have begun with both kings in the center, or with several pieces undeveloped. Another general opinion is that a middlegame starts once we’re out of theory.

A middlegame transitioning into an endgame is easier to determine, but there is no “list of prerequisites” which have to happen for a game to enter its endgame. Whether a transition is possible, and, more importantly, favorable for you, will depend on numerous factors. I have tried to explain the most important ones below.

Stjepan Tomić is a strong player and famous youtuber with his Hanging Pawns channel. His goal is to become a Grandmaster and to share his new Chess knowledge with the community.

Unlike my previous articles, and unlike most articles on the website, this one will be less “position-heavy”, and we will be going over ideas instead of example games.

The example positions are not about finding the one move or a series of moves, but about whether to attempt to steer the game towards an endgame or not, and how to go about doing it.

The term middlegame to endgame transition only sounds complicated. In reality, it means trading pieces off until there is not enough material for a strong attack on the king. In other words, simplifying a position dramatically, thus entering the endgame phase of the game.

Since the decision to enter an endgame or to try and avoid it is most commonly determined by a material count, I have divided the lesson into four chapters depending on the material balance in the position.

  • The introductory chapter covers the basic principles that should guide you when trying to decide whether an endgame would be better or worse for you.
  • The second chapter is the most obvious one – transitioning to endgame when you have a material advantage and simplifying the position would bring you closer to victory. Or, when you are material down and you should avoid the transitions
  • The third covers the most common types of middlegames, those when the material is equal. Those are also by far most complex, and determining whether entering an endgame is favorable or not will require greater general positional, strategic, and tactical skill.

General rules

Anticipating

One thing that most strong players do, and weak don’t, is anticipating possible positions which could arise in the game. The simplest example of that, which most people are familiar with is calculating tactics and imagining the resulting positions. Strong players and grandmasters go much further than that. Looking far ahead is a very powerful tool. Here I don’t mean trying to picture the exact position 20 moves ahead, but rather considering the piece placement, pawn structure, weaknesses, open files, king safety, and other general features of the position. This comes in very handy when trying to decide whether an endgame would be favorable for you.

Imagining the board without pieces

This is another very powerful tool. In your mind, try to remove all the pieces from the board, and only look at the pawn structure. Ask yourself a simple question: “If there were no pieces on the board, would this position be winning, losing, or a draw?”

It’s incredible just how powerful this technique can be. Sometimes it will give you a clear idea of how to proceed in the game, trade the pieces into an endgame, or prevent trading at any cost if the potential endgame is bad for you.

Here is an example in which I had correctly anticipated a winning rook endgame. This position occurred in a game I played last week in Bad Woerishofen Open. My opponent was rated 1945, and I have managed to put some pressure on his position out of the opening, forcing him to make a concession on the queenside.

When you are ahead in material

Another important point: If you are ahead material, it is generally a good idea to transition into an endgame. And I would like to highlight the word generally. If you have a mating attack and you are a pawn up, of course you will not trade the queens off and enter an endgame. You can win faster. There are some positions in which being a pawn up will not be enough to win, so whenever your material advantage is minimal, think twice before trying to enter an endgame.

When you are down in material

Conversely, if you are down material, endgames will generally be bad for you, and trading pieces won’t be a good idea. Again, same as in the above example, there will be exceptions, of course. One general rule is that when you are down material (meaning down a pawn or two at most), a good “drawing technique” is to trade off pawns. This will make it harder for your opponent to win the game.

Analyzing the pawn structure

A very important feature of the position you have to consider when anticipating an endgame is whose pawn structure is better, and whose pawns can be attacked and defended more easily. This can be broken down into smaller questions to make the process easier. Here are some of the most important ones:

  • Does either side have a passed pawn? Passed pawns are a huge asset in the endgame and are often decisive.
  • Does either side have a potential passed pawn?
  • How many weaknesses does each side have, and which piece would be able to target each weakness? Can the weaknesses be liquidated easily or are they fixed? Does either side have a doubled pawn, a backward pawn, an isolated pawn, or hanging pawns?

When material is equal

If the material is equal, and there are no apparent strategic or positional advantages for you, keep the position complicated ! That is a good way to avoid unnecessary simplifications and premature draws. Don’t trade pieces off until you have something exploitable in the ensuing position.

Knowing which pieces to trade

If all the pieces are on the board, or most of them at least, it will be possible for you to decide which type of endgame you want to play. That will, of course, depend on the nature of the position, and mostly rely on the pawn structure. If for example, you have a French Exchange position in which you (as white) have both rooks doubled on the e file, the only open file, then an endgame with just rooks on the board would probably be favorable for you.

Another example could be a “good knight versus bad bishop Sicilian, a position in which black has a hole on d5 which the knight could occupy.

There are numerous other advantages which are exploitable if certain trades happen, and the best way to get better at middlegame to endgame transitions is to learn how to recognize them. Planning and execution are the easy part ! Pawn structure is what most often provides you with good or bad endgame prospects. If you have two passed pawns in a middlegame with equal material, and they are controlled by your opponent’s pieces, and your opponent has none, then trading everything off would mean that you automatically win.

This example shows a good transition from a difficult position: had Bologan kept the queens on the board, he would have faced a very difficult situation !

This overview of the transition to endgame is now over. Next we are going to talk about how transitioning to endgame with a material advantage.

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