rounders poker strategy analysis

Rounders Analyzed: 3 Hands Played By Mike McDermott & Teddy KGB

What’s your favorite poker movie? And why is it Rounders?

Today we’re going to analyze 3 hands played in this iconic movie. If you haven’t seen Rounders, don’t worry: you’ll still learn from the strategy talk. That said, you should stop reading if you want to avoid spoilers!

The 3 hands we’ll discuss are played between the same two characters: the protagonist of the film, ‘Mike McDermott’ (played by Matt Damon), and ‘Teddy KGB‘, Mike’s ruthless Russian debtor (played by John Malkovich).

Let’s dive in!

Hand #1: The Mad Russian Empties Mike McD’s Pockets

The blinds are $100/$150 (for some reason).

The action folds around to Mike on the button, who looks down at A♣ 9♣. He raises to $500. The small blind folds, and Teddy calls with A A.

Mike’s raise is a bit on the larger side, but not ridiculous—it’s Teddy’s decision with aces that deserves attention. Teddy should be 3-betting with aces here to get value and build the pot, which allows him to 3-bet with some bluffs as well.

The flop is:


The pot is now $1,250. Teddy checks to Mike, who bets $2,000.

While this is definitely a flop that calls for a larger bet because it’s fairly draw-heavy, overbetting this specific size (160% pot) forces draws out of the pot that Mike wants to get value from, and it makes his bluffs more expensive, and he’ll want to bluff fairly often on an ace-high board that hits his range like this.

For these reasons, an overbet here doesn’t make a whole lot of sense. A 66% to 75% pot sized bet would be preferable.

Teddy calls, and the turn is dealt:


Teddy checks to Mike, who checks back.

Teddy has turned top boat versus Mike’s second boat, while Mike’s narration explains to the audience that he hopes Teddy will improve on the river.

Both Mike and Teddy played fine here. Teddy could have lead the turn, as he’ll have many more nines in his range than Mike. However, with his hand blocking aces out so heavily, it makes sense to check to allow Mike to continue betting with his bluffs.

Similarly, Mike’s decision to check gives Teddy a chance to improve on the river or bluff if he misses. This makes even more sense considering Mike’s blockers–he holds both an ace and a nine, making it more likely that Teddy has a draw. 

Finally, the river is dealt:


The pot is $5,250, and Teddy leads out for $15,000.

These two players certainly enjoy their overbets! And just like Mike’s overbet on the flop, this one from Teddy doesn’t make much sense; it’s difficult to imagine what he’s trying to achieve. If he’s targeting flushes, then an overbet of this size might actually get Mike to fold.

But if Mike did have a flush, a normal-sized bet would give him the chance to raise, which would result in a similar amount of money going into the pot as the overbet. Finally, Teddy could go for a check-raise, which gives Mike a chance to bluff—this is especially important given that Teddy blocks out aces so heavily, which Mike would certainly want to check back. Overall, check-raising has the most merit.

Mike raises all-in to $48,000, and Teddy calls.

There’s no getting away from this one for Mike. Second boat is far too strong to not shove, even against a 3x pot overbet. Though if it was my life savings on the line, perhaps I would make a nitty just call.

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Hand #2: When You Spot a Man’s Tell

This next hand is played heads up at $50/$100. Mike has A 5 in the big blind, and Teddy is on the button with cards unknown.

Unfortunately, the preflop action isn’t shown. We’re going to assume from the $1k pot (10 big blinds) that Teddy raised to 5bb and Mike called.

The flop is:


Mike checks with his top two pair, and Teddy bets approximately $5k (which seems to put Mike all-in).

This size is obviously a mistake. A bet this large makes bluffing extremely expensive, and it will be tough for Teddy to get called when he has a value hand.

A much more appropriate size would be around 40% of the pot for a few reasons:

  • The texture of this flop is conducive to a small bet (dry, ace-high).
  • Teddy has a large range advantage versus Mike’s calling range in the big blind.
  • Teddy is in position.

This small size will allow Teddy to force Mike to fold almost all of his non-paired hands for an inexpensive price, and he will for sure get called when Mike has hit the flop.

What happens next is one of the most famous scenes in the movie. With a snide warning “not to worry,” Teddy reaches for a chip rack of Oreo cookies, picks one up, and breaks it in two next to his ear, as though it had something to tell him. Mike notices this and, being the soul-reader that he is, realizes it’s a sign of strength. He then promptly folds face up, declaring that he doesn’t want to draw against Teddy’s flopped straight. Teddy reacts badly, throwing his Oreo stash against the wall, and proclaiming that Mike “should have paid me off on that!”

We can assume from Teddy’s tantrum that he did indeed have the flopped straight, or at least a hand stronger than top two pair. However, we can still analyze Mike’s fold from a theoretical perspective.

Strictly by the numbers, against a 5x pot overbet from a player with a balanced range, Mike needs to continue with approximately 15% of his hands (according to the minimum defense frequency). If you have a strong read on your opponent like Mike does here, you can make an adjustment and narrow you calling range accordingly; however, in this spot A5 is much too strong to be folded. It’s one of the strongest hands Mike can have, it can beat some of Teddy’s probable value betting range, and it’s still drawing live against low sets and straights. This hand simply needs to be called with on the flop no matter the opponent. 

Hand #3: Check… Check… Check… He Trapped Me!

The final hand from the movie we’ll look at is more interesting from a strategic standpoint. In particular, it shows us a good way of dealing with hyper-aggressive opponents.

Still playing $50/$100 heads-up. Mike opens to 2 big blinds preflop with 9♠ 8♠—a fairly standard open size for once, though it could be bumped up a little, especially against a loose player–and Teddy calls.

The flop comes: 

th-hearts-new-cards7s-spades-new-cards 6d-diamonds-new-cards

Mike, who now has the nuts, checks to Teddy (these two are playing an outdated form of heads-up in which the small blind acts first preflop and postflop, so this is more like a blind vs blind spot rather than a typical, modern-day heads-up spot).

Checking here is reasonable.

After flopping a straight with the initiative, Mike should usually bet, though it does make sense to occasionally slow-play a hand like this in order to protect his checking range. Against an aggressive opponent prone to overbets, however, checking is particularly good because it gives them a chance to blast off.  

Generally, vulnerable hands should be less inclined to check, as they want to avoid being outdrawn. Lucky for Mike, his hand is well-protected on this board—he’s very unlikely to be beaten by a single-card straight if an 8 or 9 comes on the turn (although he may miss out on value), and it’s a rainbow flop, so he doesn’t have to worry about Teddy turning a flush.

Teddy goes for his signature move and bets $2,000 (5x the pot). Mike calls, declaring that he’ll “gamble,” and the turn is dealt:


The pot is now $4,400 and Mike checks. Teddy bets $4,400 and Mike calls.

This check-call from Mike makes sense if he expects Teddy to continue his aggression often on the river. Otherwise, check-raising is far superior because it charges Teddy’s hands that are behind and allows Mike to capture a larger percentage of the pot on average. 

Teddy’s pot-sized bet is a good choice. Teddy has an uncapped range that benefits from bigger sizes and this size sets up stacks for a reasonably-sized overbet shove on the river.

The river is dealt:


Teddy shoves for $23,900 into a pot of $13,200. Mike calls and wins the pot.

We can’t really analyze Teddy’s shove without knowing his cards, and Mike’s decision on the river is very clear.

An interesting exercise to do as Mike in this spot is to think about what other hands we would call down with in order to avoid being exploited. After all, we can’t call with only the nuts. An obvious candidate, for instance, is AT, a hand that rivers top two and could conceivably be ahead of some of Teddy’s value hands, although perhaps not when we consider the size of the bets (it’s doubtful Teddy would overbet shove a worse two pair like T7).

Even better call candidates are T9 and T8 because they block the 98 (the hand Teddy’s representing with his size) and, given they both have gutshots on the flop and turn, aren’t as risky to check-call. Though, once again, these would be dicey calls given the size of the bets.

Rounding off

Hopefully this article has been helpful! 

Quick note: don’t eat cookies from a chip rack. That’s gross.

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Ben Ward

Ben Ward

Online and live grinder turned poker writer

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