Ciaran O’Leary, 35, of Seattle has played poker since he was 9 years old and regularly played against adults – as 9-year-olds traditionally speaking don’t have much money on them. Originally from Ireland, he moved to Boston in 1997 and played poker on his first day of arrival, turning $1000 to $3000 in under two hours. His winning ways have continued and in recent years he has hit the big time, winning a $1500 WSOP No-Limit Hold’em event for $727,000 two years ago and just over a year later placed third in the Ladbrokes Poker Million for $175,000. Ciaran has career winnings of $950,000. Today he answers your questions.
You’re in mid-position in a cash game and get dealt pocket nines, and everyone folds except the guy just before you, who bets 3 times the BB. Would you call, reraise of fold?
– Mid-Pair Master of Manchester

I must proceed here with caution given the fact that I’m in middle position with a bet already in from my immediate right…not to mention – I have no way of knowing at this point what the other players around back of me are going to do, so therefore depending on who the bet came from and on my read…a raise might well be the course of action, which will also make it harder for someone around back to play with a marginal hand.
 
I love tournament poker and I do seem to get pretty deep in the game, but in the last three I’ve gone out the exact same way. My overpair or top two pair runs into trips. Any advice on how to avoid this?
– Sally Gunther, London

The situation you’re describing is a fairly common one as the person who holds the overpair or two pair is always going to find it hard to see that he is beat and release his hand, so don’t beat yourself up too much about it! One thing to look out for, though, is the fact that you had the overpair and were beaten by a set/trips might mean that you may want to try and put in a bigger raise preflop to price out and make it harder for the small to middle pairs to call you, so then there will be less chance to be outdrawn by the set.
    The only problem here is that you do have a tendency to give away the strength of your hand if you have a hand like tens or jacks and you make it four BBs…typically this is seen by a more advanced player as the type of hand that you hold but at least they won’t try and run ya down with a smaller pair. And if someone does call – just hope your hand holds up and make them pay on every street!

Do you think there is any situation where you can lay down K-K preflop?
– Drake Chambers, Monte Carlo

Wow – I believe there is, but it’s not easy! I think it comes down to knowing your player and knowing the situation you’re in. If he’s a rock and it’s a raise/reraise/re-reraise, well, then the alarm bells should be going off as he has to have something, right? Also too – if it’s in a huge event like EPT, WPT or WSOP Main then you could pass/fold providing you’re not too much invested. Now if it’s my good friend Roland [de Wolfe], I’m not passing at all as he falls into the category of very aggressive and might be playing anything as hard.

In a small cash game, I raise from mid-position with A-5 diamonds and get called by the BB. The flop comes 2-7-10, we both check; a deuce comes on the turn, both check. A seven comes on the river and the BB bets three-quarters of the pot. Do I call hoping my ace-high wins, or do I fold?  
– Ace King of Prague

The board has paired and with the type of cards that are often found in the blinds, not to mention the fact that you haven’t already put in a bet on the flop or turn, why would you bother now calling his bet on the end? He could easily have a hand like Q-10 or A-2 – fold.

The later stages of tournaments always seem to turn into crapshoots where players are forced to push all-in on every hand they bet. In situations like this do you think I should bluff to acquire chips and risk running into a good hand or wait for the goods but risk being anted away?
– Karen Winter from Nice

Many people play tournaments different ways. Some are trying to play their way into the money and get some cashes under their belts; there are those who are playing to get deep and if they can somehow make the final table then they would be delighted, and then there are those who only want one thing – to win it – and would rather be out in the first hour than be anted off with only 20 players remaining. Of course, you have to be a realist here as “it’s not easy to win these things!” Keep in mind, though, that almost 70 percent of the prize money is paid out to the top three players, so the more chips you have early the better your chances of getting to where you need to go…and that’s the final table, my friends. This then avoids the all-in move when it’s the only arsenal left in the bag.

I recently started playing poker and have been taking part in a lot of small-stakes rebuy tournaments. Do you have any rebuy strategies?
– Derrick Kendal, London

Give yourself a max amount that you are going to spend, as you don’t want to pump too much into any one event. From a poker strategy standpoint, I would be prepared to gamble a bit more in the early rounds. I would take a lot more coin-flips and would be three-betting it on some big draws to accumulate as many chips as I could. Oh, and have fun!

A few times in my poker life I’ve been lucky enough to flop the nuts, be it an ace-high flush, straight and sometimes even a full house. Unfortunately, my joy always seems to be short-lived because having hit so huge, everybody else seems to miss. Naturally, I check on the flop and sometimes even the turn if everyone looks timid, but even after all that a small bet on the river and everyone’s gone. Meaning my monsters take tiny pots – any ideas on how to make them pay more?
– Clueless in Cairo

The sun, moon and stars often need to align in order for you to have your way at the poker table. That’s what makes the game so appealing, I think, because when does that ever seem to happen? However, we continue to hope, but I’m sad to say that…“Hope is not a strategy.” Not much you can do, sir, if your opponent doesn’t have anything. Just for the fun of it…try leading out and bet it the next time you flop the nuts, especially the full house, as they are less likely to put you on it by doing that and might try and bluff you.

If you’re short-stacked in the later stages of a tournament, what’s the best hand to go all-in with that isn’t a premium hand (A-10 to A-K, J-J or better)?

– Adriano Boundson, Milan

I’m not a big fan of shoving with a hand like ace-rag, as typically it’s a bigger ace that ends up calling you. You must also be careful when there’s no action around to you and you’re in the cut-off pushing with a hand like K-9 or Q-J because the fact that no one has entered the pot yet raises the possibility that no one had an ace, which now raises the chance of the three remaining players waking up with a big ace…hmm – you see – it’s never easy. If you do feel compelled to move in, truth be told, the K-9 and Q-J might well be the best hand that you are going to see with only a few hands left in you!

I’ve mostly played tournament games but would really like to get into playing cash – how should I change my game?

– Alex Johnston from Bristol

The game is the same; it’s how you play that is different. You don’t have the luxury in a freezeout event to reload after you get knocked out. In an event, you can only lose the amount of your buy-in and of course it might also be the only chance that you would ever get to sit down and play against some of the best players in the game, as you wouldn’t ever dream of sitting down and playing against them in the high/high limit games that they play in. Regarding your strategy for cash games, set yourself some boundaries. Start at the lower levels and move up slowly. Never put more than 5 percent of your bankroll on the table at any given time. If you are having a bad day, consider finishing early, as it will most likely save you some money. Try learning from your mistakes, my friends, and remember: “No matter how good you are, you’re not going to beat the game every time you play it as there are just far too many things that are out of our control.” And last but not least, enjoy what you’re doing also – when it stops being fun, you might need a break.

Here’s a hand I was playing the other night: Everybody folds to me in the cut-off position and I’m holding A-K spades. I raise 3 times the BB and get a call from the button, SB folds, BB calls. The flop comes 3-10-J (rainbow, three of spades). I bet out, button flat calls again, BB folds. Turn is ten of spades. I check and so does the button. The river brings the jack of spades, I make a mid-size bet to test the water and he massively overbets by pushing all-in, effectively wiping me out if I lose. Do I take this as a bluff or do I call knowing any ten or jack wipes me out?

– Bad Hand Luck, Birmingham

It may very well be the case here that it went runner-runner for the both of you and he has backed into a full house and you ended up making your nut flush. If it were me I would fold given the fact that I don’t have much invested in the pot and he’d be making a suicide move if he were shoving with nothing as you could easily have a house yourself. Remember: “The great thing about poker is you don’t have to win every hand you play.”

I was playing in the opening stages of a tournament when I picked up pocket queens in early position. I made a four BB raise, everybody folds to the cut-off, who re-raised me three times my original bet, or about a third of my total stack all together. I thought about it and called, deciding to release it if an ace or a king appeared. The flop came ten-high. I bet out about two-thirds of the pot and he instantly pushes all-in. I still have a little under 50 percent of my chips left and the blinds are still low – a comeback is possible if I fold. Do you think I should fold or call?

– Casey Jones, London

He most likely did not put you on queens here when you didn’t reraise him preflop. With this in mind if he has J-J he may feel that he is the one that is ahead and might put you on a hand like A-K. If I play the hand the way you did I’m probably calling here. If he shows you K-K or A-A then it’s just a cold deck. I don’t think he is going to shove with a set when you are betting into him.
    Again, depending on the size of the tournament, if it’s a small freezeout there’s a chance he doesn’t really care too much and might be shoving with A-10 and thinks he’s ahead.
    I might have reraised preflop rather than just calling his raise and if he pushed then at least you would know you were flipping or were a dog!

How should I play suited connectors in a six-handed cash game?

– The French Connection, Paris

Carefully!

What do you think is the most important characteristic to being a good poker player – mathematical skill,  intuition, patience, etc.?

– Newbie in Sheffield

All of the above is needed if you want to be a top-tier player. If you have one and not the others then you should try and work on them. Instincts and also trusting your initial gut feelings are also crucial in making the journey. I personally believe we have the ability to go to the next level/zone when tapping into this. When you consider what the human body can do, then is it any wonder that if we were open to listening to what our own bodies are telling us we might all do a
little better?  MY personal belief is: If I trust my feel/read/instincts and how momentum is going, etc…then four out of five times I should be right.

With poker tournaments being so expensive to enter these days, it seems the only real way to take part is to win a satellite. Do you have any satellite tips that might help me get a seat at the WSOP Main Event?

– Charlotte Church, Edinburgh 
 
Satellites are a great way to get your seat and I believe are a major key to keeping the supply strong. After all, who can afford to put in these huge chunks of money week in week out! Anyway, if you follow this very straightforward method when playing satellites – you should do very well!
    I like to know a few things from the start:

    1: How many do we have playing in it?
    2: How many seats are they giving away?
    3: What is the total amount of chips that are in play?

    From there I do the following. Let’s use this easy example.
    There are 100 players. They are giving away ten seats. Each person is getting 1000 in chips, which makes 100,000 total chips in play. What I do now is work out the average stack that people are going to have with ten players remaining, which is of course 10k. So I’m starting with 1000 and if I can build my stack to 10k then a seat will surely come to me. But let’s take it one step further. I know that some people are going to have around 20k and some will have 15k so now that drops the average for everyone else. So if I can get to 5k or 6k and then play shrewd it may very well get me my seat. You see you are always gong to have two or three people with some huge stacks, which means you are also going to have some very small stacks – people just hanging in there with 2k or 3k, so remember if you find yourself in the second level with 5k already then be aware of this and know that what you want to do is at least maintain that amount. Add to it if you can but don’t go taking any coin-flips with people who can hurt your stack because whether you have 3k or 30k when the bubble boy is knocked out you still get the same, and that is a seat.
    In 2004, I won four seats for the WSOP Main Event using this strategy (and some good play, I might add).