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Run it Twice -- Jay Rosenkrantz Heads-Up Poker Hand

Rosenkrantz Talks About a Heads-Up Hand Against Tom Dwan

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Jay Rosenkrantz is a 25-year-old high-stakes cash-game pro who resides in New York City. In 2007, he was named the biggest winner online in no-limit hold’em cash games playing under the screenames “pr1nnyraid” on Full Tilt and “purplEUROS” on PokerStars. He is known not only for his instinctual and dangerous talent playing the game, but also his renowned ability to teach it. He’s a founder of the online training site Deuces Cracked. The following question and answer is featured in his profile on the site.

Q. Describe the best hand you’ve ever played.

A. I’ve made some crazy hero calls. I remember one nasty jack-high call on an A-9-6-K-K board I made in Monte Carlo while “danzasmack” was sitting next to me, watching and wincing.

But off the top of my head, there’s one hand I should acknowledge. It was a $120,000 pot against “durrrr,” by far the largest pot I had ever played at the time, right when I was moving up through $50-$100 NL [no-limit hold’em] and higher. We were playing an insane match at $100-$200 NL across four tables, and I’d been reraising him a ton. So $60,000 deep, I repopped 5-3 and flopped an open-ender. I bet; he called. I double-barrel semi-bluffed the offsuit king turn, and he thought and called. The river was an ace, giving me the nuts (and unbeknownst to me, making him two pair). Overbetting all in crossed my mind, and I was debating betting pot and check-raising too — but I knew if I was going to overbet, I needed to do it quickly, because of various timing factors. So, I just went for the glory and jammed, and he called quickly. Man, winning that pot was awesome, and it gave me the confidence and momentum to move up through $200-$400 and maintain a long run at the nosebleed stakes."

For this edition of Run It Twice, Rosenkrantz sat down with Card Player to discuss a hand that was a major turning point in his career.

The Game

Game: No-limit hold’em
Stakes: $50-$100
Type: Heads up

The Roster

  • Jay Rosenkrantz
  • Tom Dwan

Run it Twice — Review of the Hand

Kristy Arnett: How long ago did this hand take place?

Jay Rosenkrantz: This was two-and-a-half or three years ago.

KA: You mentioned that this was one of the first times you’d been playing that high. Did the amount of money that was being exchanged intimidate you?

JR: The swings were big, and there was sort of a surrealism looking at the dollar amounts, but not really. I didn’t really start to feel the weight of the monetary differences until I started having six-figure losing days after I’d run hot in the beginning playing $200-$400. That’s when it started to affect me. I’ve always been pretty good about looking it at the monetary amounts as chips and not in terms of actually money.

Preflop Action: Dwan raised on the button, and Rosenkrantz reraised with 5Spade Suit 3Spade Suit. Dwan called.

KA: Why did you decide to reraise this hand?

JR: People were playing very differently back then. They weren’t as adept at no-limit [hold’em]. Reraising with a hand like that out of position against most good players is kind of bad now, because they play so well post-flop. Back then, it worked, because I was able to win a lot of pots by continuation-betting. For heads-up beginners, the good thing about reraising a hand like this is that by taking the initiative, you can take down the pot when you miss and your opponent [also] misses. You can put a lot of pressure on him by putting a lot of money in the pot with a marginal hand. You start taking these pots down preflop and start building an aggressive table image, you’ll get paid off when you get aces or kings.

KA: Do you remember what the bet-sizing was?

JR: I have no idea, it was so long ago. I’d imagine that since the stacks are so deep, we were raising four times the bet.

Flop Action: The flop came 9-4-2 rainbow. Rosenkrantz bet, and Dwan called.

KA: In a reraised pot, what kinds of things are considering when deciding whether to check or bet this flop?

JR: The first thing I look at is the board texture, and consider what types of hands he might be defending a reraise with, what he would do if I bet, and what he would do if I checked. I’ve got to think about what I want out of the hand, and I also have to think about what he would do with marginal hands. What would he do if he flopped a 4, what would he do if he flopped a 7? What does he think I’m considering? What would he think if I checked on this board? It is such a good board to continuation-bet on, because it’s so dry, so sometimes, if I had a hand that clearly didn’t connect, I might check against a really good player to out-level them on later streets. In actuality, I’m making it look like I have a hand that I’m trying to control the pot with, but with complete nothing. I’d say, though, that a very high percentage of the time, I’m continuation-betting here because that’s what I would do with aces, kings, and a set. I think in the context of a long match against a really good player, like Tom, I might check more often, just to throw their reads off. When you show up with hands that they don’t expect you to have, then you are doing things right against the really good hand readers. Anyway, betting here is the standard, and that’s what I did.

KA: What are you thinking when he just called? Does this surprise you, or do you think he’d be calling here with a lot of his range?

JR: No, it doesn’t surprise me, and it doesn’t bother me either because we’re so deep, and I have an eight-out draw. I also have cards that could come that I can use to my advantage.

Turn Action: The turn was an offsuit king. The board read 9-4-2-K. Rosenkrantz bet, and Dwan called.

KA: Was the king one of those cards?

JR: Yeah, when the king comes on the turn, I can still bet and rep hands like K-Q, A-K, K-J, and K-10 even. I can take him off his ace-high hands and complete floats. We’re really deep, and he’s really loose, so he can literally have any two cards there. I would think that he generally is not going to have a set, because sets would usually raise the flop that deep.

There’s no reason to check that turn, because very often I can just win the pot with another bet. He’ll just fold his ace high, he may fold a small pair, and if he doesn’t fold here, he might fold on the river, depending on the card. I think the standard in this situation is to keep betting. In order to balance my play, I would do that with aces, A-K, or set. Basically, I’m trying to say that the only way I’d vary my play by checking the flop or turn is if I have a really good read or think there is a good chance that he’d be more prone to float on this flop or to bet with marginal hands in position. And that goes for when I have a big hand and I’m considering whether to bet or not, or check also.

KA: When you are so deep, what are you considering when deciding on a bet size on the turn?

JR: Pretty much now what goes through my head was completely different that what used to go through my head, back with I played this hand. Bet-sizing was the last thing I thought about. I got lucky in that I was able to make it to pretty high stakes without considering adjusting my bet-sizing. I was kind of a big bettor. I didn’t think about the value of small bets, so that’s something I’ve really added to my game in the past couple of years. Back then, what I was most concerned about was making a bet that looked sort of like I had a king or better; I was going for the value-bet type look. So, something was around two-thirds of the pot. Since we were so deep, the river bet is going to be an overbet, anyway. Something, that lets me put all of my money in if I hit my hand, but also something I can bluff all in with on the river if I feel like it will work. If your bet is too small, you run the risk of getting raised off your hand. You also run the risk of not being able to bluff for enough on the river to get him to fold to give him bad odds to call.

River Action: The river was an A. The board read 9-4-2-K-A. Rosenkrantz went all in, and Dwan called. Rosenkrantz won the $120,000 pot with the wheel straight.

KA: Why did you decide to go with the all-in overbet play on the river?

JR: After I hit my hand, I was just thinking about extracting value. I quickly ruled out checking because he just can’t bet a lot of hands that he has. If he’s got a stubborn pair of tens or a stubborn eight, which was top pair on the flop, he’s not going to bet those hands at all unless he’s making a really sophisticated rare kind of play, which is turning a made hand into a bluff that would move me off something like jacks or K-Q. I can’t expect him to do that. I think he’d be happy to get to showdown with those hands. I think from a game theoretically-optimal strategy, when you are playing against a good player who checks that river to you, shoving almost any hand is going to be a profitable play. Most often, when a player checks the river there, they are either giving up on a bluff or they’ve got a really difficult call to make. So, now the question becomes, “I know I need to bet, but how much should I be betting, and why?” Then I start to think, all right, what would I do if I were bluffing? How many bluffs can I actually have in my range that would bet the flop and the turn? I can have a lot, since I was reraising quite a bit. There are a bunch of different gutshots on the flop, and the turn brings an overcard and more gutshots, and the river brings the Big Daddy overcard, and that can conceivably be a spot to bluff. I could have J-10, I could have Q-J, I could have 6-5 suited, or something like that. Now I need to think that there are bluffs I could represent, so now I think I definitely need to bet big. In a spot where you’ve either got the nuts or you’re on a bluff, you want to bet big and polarize your range. Going through all of this in my head in the 20 or 30 seconds you get online, my gut told me to overbet all in to really polarize my range to say, “Hey, I was bluffing the whole way, and I’m continuing my bluff on the river,” or to say that I have the nuts, which would be like a set or A-K, and obviously 5-3 is the pure nuts. I think it was 1.5 or 2 times the pot. I bet all in, and he called with A-9.

He had two-pair, but in reality, though, even though he improved on the river, he still has the same relative hand strength. It’s a bluff-catcher, because by me making that polarizing bet on the river, I declared to him that I have A-K or better, or I’m bluffing. He has a hand that only beats those bluffs.

KA: Though you could represent a bluff with an all-in bet, would you have done it if the river were a blank and you missed your draw?

JR: That is hard to say. I have to consider his tendency to call. I don’t think I would have bet all in on a bluff. I think I would have bet three-quarters of the pot. By doing that, I’m depolarizing my range, saying, “Hey, I’ve got a lot more possible hands that I could be betting this river with. Not only bluffs, but hands for thin value like K-Q or K-J, because I know that Tom is prone to make ridiculous hero calls, and he might just call me down with 9-8. So, I might have made that three-quarters bet to represent more hands besides just a super powerful hand.


Rosenkrantz is a founder, coach, and instructor for Deuces Cracked, a poker training service that provides in-depth instruction. Videos and blog entries by Rosenkrantz can be found on the Deuces Cracked website.