Sunday Special We Enter Captain Nath's Jackpot Lounge

We hit the jackpot turn, but see an ugly river.

My thoughts are included in the footnotes. If you reading this via e-mail, it might be an easier read on Substack where the footnotes require less scrolling back and forth. Click here.

Greetings readers! A little background on me: My name is Nath Pizzolatto, or, as some people know me per the one of the screen names I picked back in 2005 that stuck as a nickname, Cap’nJackpot. I was part of that generation of online players who came up then, largely studying and discussing the game on the old 2+2 forums. I had some success at the game for a few years, particularly with very aggressive tournament play and as an early adopter of smaller open-raise sizes, but I never had a big breakthrough.

That’s a long way of saying that 20 years ago I was almost somebody.

After Black Friday I had to go back into the ordinary world, where I worked in a lot of different jobs and on a lot of different projects and hobbies— finishing school, food and drink journalism, NFL Draft analytics, standup comedy, TV production, TV and music criticism, songwriting, board game design, podcasting, streaming… uh, accounting and tax consulting— that I can tell you about in my own time. (I’m what they call a ‘Renaissance Man,” in that I’m a dilettante at a lot of things and not good enough at any of them to call one a career.)

Now for the present day: I started playing poker again seriously in 2021, and the fact that I had so much to learn, now that solvers had been introduced into the poker ecosystem, made the game engaging in a way it hadn’t been in a long time. (I suspect the maturity of age and living a healthier lifestyle in a healthier environment has helped me a lot in this regard. If you knew me back then, I was… let’s say, not the most emotionally stable player.) So I’m back at tournaments when I have the time to play.

I am also the copy editor here at Punt of the Day. So if you appreciate the grammatical consistency and correctness in Sam’s posts, or the cheeky editor’s notes occasionally inserted, or just that his editor actually knows exactly what he’s talking about when he writes about things like Roger Ebert zero-star reviews of otherwise long-forgotten movies… that was me, you’re welcome.

I’m also in the midst of launching my own poker content site, smashing my real name and poker screen name together to create Captain Nath’s Jackpot Lounge. So I’ve been blogging and vlogging there for now, although I am in part still trying to figure out what I want it to be, because that in part depends on what the audience wants. One thing I am sure I want to have: My new podcast called Cards Speak, where my intention is to have more in-depth conversations with notable poker players about life beyond the game. (You can read about it in more detail on the “About” page at my website.) If you sign up to my Patreon, you can get some exclusive content there (eventually) and submit questions to future guests (even now), among other perks. We’ve already booked a couple of notable guests in the poker world, and should launch within the next couple of weeks, pending scheduling and my own editing/production skills.

OK! Let’s move onto a hand I thought was pretty interesting. This is from the $33 40k early-evening tournament that used to run on ClubWPT Gold (it is currently a $33 100k mystery bounty) on November 9, 2025. (Hey, remember the November Nine? I haven’t even cashed once in the WSOP Main in six attempts.) One leak of mine I’ve been working on is playing too passively for fear of making a mistake, and I’m trying to do that less. (This is rather ironic if you knew the kind of unhinged maniac I used to be.)

Here, I have 99 in the CO facing a HJ open. It’s a hand I would flat a lot, but I think I’m supposed to mix in 3-bets in this scenario, and I had read somewhere recently (probably here on Punt of the Day) that there is value in raise/calling hands like this when it’s late position vs. late position. I have 45BB and my opponent covers me by a bit. Unfortunately, ClubWPT Gold doesn’t save hand histories, but I recorded as much detail on this one as I could at the time, because I knew I would want to review it later.

We are nearing the end of late registration, so there’s no real ICM pressure, but I do have about four starting stacks at this point, and I don’t want to just blow that, either.

I get a pretty unusual spot here, with a flop that’s not good for me, and a turn card that seems very good but still leaves me in a weird spot, with a very strong but vulnerable and not-nutted hand. How did I navigate it? Read on! Did I screw it up? Read Sam’s footnotes!

ClubWPT Gold $33 40k
10-minute levels, late registration ends in 15 minutes or so.

8-handed

Preflop: Folds to villain (49BB) in HJ who raises 2.2BB, I (45BB) am in the CO and 3-bet 9♦️9♥️ to 7BB, it folds back to the HJ who calls.

Flop (16.5BB) Q♣️ T♣️ 5♠️: Villain checks, I check.

Turn (16.5BB) 9♣️: Villain checks, I bet 8.25BB, villain calls.

River (33BB) 8♦️: Villain checks, I check.

What The Hell Was I Thinking

Preflop: As I said, I often flat this spot, and it might be a safer play, but our positions are late enough that I also thought I could 3-bet for value sometimes.¹ I would say I randomized and rolled high, but that would be a lie; my process was more like “I feel like I’ve been leaning toward more passive and low-variance lines lately in spots I shouldn’t, and this seems like a good spot to take the more aggressive approach.”² Our villain calls the 3-bet, though, so it looks like we have to play some poker; at least I’m probably still pretty good at doing that (and I have position even if I’m not).

On the flop… well, that’s pretty crappy for me. On the one hand, there are enough high cards here that I could reasonably hit, such that making a small bet with range is probably reasonable. In the moment, I considered what I thought of villain’s calling range, and concluded that they either hit this flop or have some kind of draw that won’t fold.³ I’m not sure what I can get to fold other than pairs lower than mine, which are a small part of his range and only have about 10% equity right now anyway. Maybe I get AJ no club to fold, but probably not for 20% pot. And sizing up with third pair in a 3-bet pot feels like a chip bonfire.⁴ I have no club, and every Broadway hand has a pair or a draw on this board. I could fold the best hand if he plays those draws aggressively on the flop.

In sum, this flop is bad for my hand and a lot of turn cards are bad for my hand. So I decided to check to see what the turn would be and how our villain would play it, hoping for a safe turn card and a check, and ideally a 9.⁵

Then on the turn, I hit probably the second-best card for me (other than the 9s). Now I have a set! A set is a good hand.⁶ Unfortunately, it is also far from nutted— the 9c also brings in the flush and completes the straight for KJ. And though there may only be a few combos relevant here… I also have third set, and villain could definitely flat preflop with TT (and possibly QQ sometimes). So while a set is a strong hand, I lose to KJ, QQ, TT, and any club combos villain has (probably a lot of the AcXc and KcXc they opened, maybe if they have medium-to-low suited connectors in their range here too).

Once our villain checks, though, I figure that my hand is probably best but is vulnerable to a lot of one-card draws. I feel like the check indicates some kind of made hand that will take a showdown, but not one strong enough to bet here. Maybe something like QJ with a club. I figure an unpaired hand like AJ with a club (and maybe without) might lead here— or maybe with a club decide they have enough equity to check-call.

In any case, I was going to call a bet if villain bet, of course.⁷ Now that villain has checked, I bet my hand for value and protection. Seems pretty straightforward: At this point, I have every reason to think I have the best hand, but I don’t want to pile in so much money that I only get called when I’m wrong, and I also want to charge any one-card draws to see a river.⁸ So I bet half pot⁹ and get called.

On the river: Wow, that sucks! One-card straight comes in. I don’t think I can value bet my hand anymore.¹⁰ Thankfully, our villain checked to me, so I can just take the showdown.

I saved villain’s hand for the end so as not to ruin the surprise. I lost to QQ.

My Solver Review

To estimate the ranges here, I looked at a mix of the 40BB and 50BB chipEV sims over at Punt of the Day partner Octopi Poker. I think based on our actual stack sizes, it should play closer to 50BB than 40BB, but I’m not sure.

Anyway, 99 is indeed a mix. At 40BB we 3-bet 43% of the time; at 50BB we 3-bet 23% of the time. I don’t know if my frequencies were exactly correct here, especially because my randomization process was “I don’t think I 3-bet these enough and this seems like a good spot to.” It’s probably fine, although my 3-bet is slightly larger than it needs to be.¹¹ I figure that can’t be too big a mistake since it just means I play a slightly bigger pot in position.

Villain is supposed to 4-bet QQ 100% of the time here, however, mixing jams at 40BB but always non-all-in at 50BB.

On the flop: I do mix checks and b20 with all combos of 99, most frequently betting when I have the 9s but not the 9c. I bet least frequency with the 9c (and least of all with 9s9c). My combo is the one remaining combo that fits right in the middle— 55-57% bet, 43-45% check. Again, I can’t say I checked for randomization; I checked because of the reasons I described above.¹² And since villain showed up with QQ here when they should never have it, then they may be playing tighter and more passively in response to the 3-bet than the solver. That may mean the HJ has other hands they shouldn’t have here that also beat me— and I think even more to the point, is calling preflop with fewer of the hands I can actually get value against.¹³

Looking at the solver, I don’t hate my check at all. The HJ not only would have to continue as wide as the solver to make betting a good play— and the crappiest straight draws villain is supposed to continue with have a 9 in them, J9s/98s, and I block those— but I can also get bluff-raised off the hand by something like AJ with one club. (I’m supposed to continue against a check-raise sometimes with the 9c, but I don’t have that.)¹⁴

In short, I think my check back here is probably preferable against this villain, who in hindsight seems to have a tighter and stronger range in this spot than the solver would.

Admittedly, I figured all in all I would bet more often with the 9c than less often, and that was incorrect. I believe I thought the slight backdoor-flush equity made betting more appealing. I would surmise the solver output is likely because when I have 99 with a club and get called, I am a little more likely to be up against a made hand that beats me instead of a club draw than when I have 99 without a club.¹⁵

On the turn, after HJ checks, I am supposed to bet my 99 here (always at 50BB, almost always at 40BB). The preferred size is quarter pot, however, and half pot is a very infrequently used size. I’m not sure why, exactly.¹⁶ Maybe because we want to charge draws and weaker made hands without shutting out too many of the latter, and without making the pot too large with a hand that, for however strong it is, a lot of rivers are terrible for; it’s also a hand where I might throw up if I got check-shoved on after a half-pot bet. (And then I probably call because who check-shoves a straight or flush here? Well, maybe if they have KJ no club and don’t want to give an action-killing or even pot-losing free card. Okay, yeah, the throwing-up line is entirely plausible.)¹⁷ I think I chose the larger size because objectively my hand is quite strong and I thought I could still get calls from worse made hands (and certain draws— I don’t think any hand with the Jc is folding here), and also, getting a fold here is far from the worst thing in the world. All in all, I think I thought about the purpose of my bet correctly, but I chose the wrong size for that actual purpose and could have bet smaller.

The river is a very straightforward check-back from me whether I have 40 or 50BB and whether I bet quarter pot or half pot on the turn. I am just thankful I didn’t get donk-jammed on.¹⁸

Conclusion

I think overall I played this hand pretty well, although it certainly left me with a nagging feeling afterward (mostly because, well, I lost a pretty big pot and ⅓ of my stack). I need to get better at some of the nuances the solver finds, and more importantly, understanding why the solver finds them. My sizes were a bit off, and while every street except the river check-back was a mix, I also chose the least frequent decision at each of my first three decision points.¹⁹ That said, even though I went down the less frequent road at every step, I felt like my rationale at each decision point was sound. The only thing I’m really thinking about is that I didn’t need to bet so large on the turn.²⁰ All in all, though, I think a fairly well-played hand, albeit one that does reveal a couple of areas where I could stand to polish up the finer points of my game.

If you made it to the end of the post and are interested in being the subject of a future Sunday Special, let me know. Do not be shy if you have a lack poker skill or accomplishments. No solver analysis is required from you and I’d much rather have hobbyist poker players, who are good writers that can produce clean copies and clearly articulate their thought process than editing the writing of 99% of accomplished poker players.

1. Especially in low stakes games where people might just call three bets OOP too loose.

2. If you play versus the same opponents this sort of trend can be predictable, but I doubt that’s a concern in $33 with 1000+ runners.

3. A good rule of thumb is you play king high boards a lot more aggressively and often range bet them because your opponent should never have AK and you might always have it. On queen high boards that effect is often flipped because you rarely three bet AQ, unless you want to stack it off preflop and your opponent almost always call AQ OOP

4. You’re never getting better hands to fold, but you have a hand that can find some profitable turn and river bluffs on 8,J,KA turns.

5. This logic is all sound to me, especially if you’re not worried about your opponent frequently bluffing into your check back range.

6. Agreed

7. Depending on villain’s size, I might raise the turn, but generally I’d call.

8. It’s also a spot where getting all-in on a blank river should be pretty easy.

9. Half pot represents a pretty strong hand and your range doesn’t look like you have many very strong hands. So the solver prefers blocking, but half pot seems like a good greedy exploit vs the population.

10. This seems close and I am legitimately unsure, but if it’s a bet, it can’t be making much.

11. I think the size is a little too large, but a reminder that the sizes in many public libraries are not rigorously tested because it doesn’t matter all that much. The EV difference between betting 66% pot and 72% pot is miniscule postflop and preflop. This is all to say just because you picked a size that Octopi or GTO Wizard or GTO Lab did not does not mean you are wrong, it’s possible they are wrong.

12. I think often times checking this class of hand sort of turns your hand faceup. however in this situation checking makes your hand look like AK/AJ/Tx, so it’s nice to check back a hand like 99 that will get too much credit on A,K,J,T turns and not enough credit on 9x turns.

13. It’s possible he overfolds to a three bet, but there is a class of loose-passive player who just hates playing aggressively preflop. They’d call QQ here and they’d call KTo here.

14. I’d assume you’re continuing vs a very small check-raise here and it’s worth very little. So I would not call a check-raise vs almost any actual humans.

15. This is counterintuitive and what’s going on is the backdoor flush draw gives you more playability on turns and rivers so you’d rather see a turn with 9c9x and you’re fine bet-folding 9h9d.

16. I wrote about this above, but it’s partially that you’re not really repping any strong hands that want to stack off. Your range looks much more like AT and JJ betting for protection/thin value than flushes/straights/sets.

17. I’m pretty happy to bet-call here. There are a lot of two pair combos or KhQx type combos and our hand really does not look like a set or better.

18. I did look it up and the solver does pure check here, there are some surprising non human value-bets on four straight boards with a small stack to pot ratio and I always like investigating hands to see if the option is available, but it’s not a play here.

19. If you are always picking the least common play that doesn’t lose EV, that’s an issue. If you are concsciously trying to exploit your opponents or try to hit the infrequent plays to make your own game less predictable, that’s good.

20. A common play from hobbyist poker players is they like betting large on dynamic boards to deny equity or charge their opponent. Often times the solver likes treading carefully and waiting for safe rivers before letting the pot get really big, this is one of those times.