Can you make four (4) nines (9) equal 100?

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Use the digits from 1 up to 9 and make 100.

Follow the rules.
=> Each digit should be used only once.
=> You can only use addition.
=> For making a number, two single digits can be combined (for example, 4 and 2 can be combined to form 42 or 24)
=> A fraction can also be made by combining the two single digits (for example, 4 and 2 can be combined to form 4/2 or 2/4)

Question: how can we do this?

John and Jacob are playing bets. John gives $10 to Jacob and Jacob deals four cards out of a normal 52-card deck which are chosen by him completely randomly. Jacob keeps them facing down takes the first card and shows it to John. John has a choice of either keeping it or looking at the second card. When the second card is shown to him, he again has the choice of keeping or looking at the third which is followed by the third card as well; only if he does not want the third card, he will have to keep the fourth card.

If the card that John is choosing is n, Jacob will give it to him. Then the cards will be shuffled and the game will be played repeatedly. Now you might think that it all depends on chance, but John has come up with a strategy that will help him turn the favor in his odds.

Can you deduce the strategy of John?

I know a ten-letter word in the English language which can be typed using only the top rows of the computer keyboard.