In essence, yeah, it is kind of a broken shape. However, it also destabilises Black's group, which no longer really has two eyes (1.5 I think). So, how does it differ from this clearly broken and bad shape?
- Click Here To Show Diagram Code
[go]$$Bcm11 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . 9 X . . |
$$ | . . . , . . . . . , . . . . . , 8 . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X , X . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
It's just a matter of distance. For one thing, Black could of course play

@ Q10, and I'm likely to simply lose out on the edge, and secondly, it's harder for me to find a way of looking after

in general. Looking after that stone in some way is important, as the idea here is to force Black out whilst I neutralise Black's right side development.
I'm also not entirely convinced it's globally bigger than the bottom side or the left side, although out of the two I'd somewhat prioritise the lower side. However, my reasoning for playing it now is as follows:
When Black chose to extend rather than jump, he chose to develop the right hand side with a bend (at least, that's the normal continuation). Hence the diagram I showed with a crazy fight developing in the top right a couple of moves ago. If he gets to play that bend, it's pretty annoying for me:
- Click Here To Show Diagram Code
[go]$$Bcm17 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . 3 X . . |
$$ | . . . , . . . . . , . . . . . , . . . |
$$ | . . . . . . . . . . . . . . 5 . 4 . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X , X . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]

may be a bit soft, but even if he doesn't kill, sealing in with outstanding thickness is very worrying for me. Not only that, but I can't play a bit looser and hope things go any better:
- Click Here To Show Diagram Code
[go]$$Bcm17 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . 3 X . . |
$$ | . . . , . . . . . , . . . . . , . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . 5 . 4 . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X , X . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
This is still a world of hurt for White, so if I'm going to pincer, it has to be before he gets that bend in. Why pincer at all?
Well, my local followups fix the fact he hasn't yet settled his group, and quickly give him 4th line territory that's hard to invade:
- Click Here To Show Diagram Code
[go]$$Bcm17 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . . X . . |
$$ | . . . , . . . . . , . . . . 2 , . . . |
$$ | . . . . . . . . . . . . . . 4 3 . . . |
$$ | . . . . . . . . . . . . . . . 5 . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X , X . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
There's no way now I can prevent him making 30 or so points, and I just can't get compensation for that, leading me to believe that moving over the top with

is not particularly clever. Of course, I can't afford to pincer and end up attacked a la the previous diagram, so having miai of base + connect is very valuable indeed:
- Click Here To Show Diagram Code
[go]$$Bcm17 w20 could also be at "a"
$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . 4 X . . |
$$ | . . . , . . . . . , . . . . a 6 5 . . |
$$ | . . . . . . . . . . . . . . . 8 2 7 . |
$$ | . . . . . . . . . . . . . . . . . 9 . |
$$ | . . . . . . . . . . . . . . . . 3 . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X , X . . |
$$ | . . . . . . 0 . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
Pressing Black down in this way is a great result for Black - it destroys the development that Black wanted to make with the lower right corner (i.e. fast development on the right side), and allows me to keep sente to boot. Because I can make a two space extension towards the lower right in some way, I have enough space to play with that I should be very hard to attack. If Black extends out, I have to jump, and I assume he'll extend out again or the first one seems lacking in purpose. As I want to develop the lower side as well, I'm going to try a probe:
- Click Here To Show Diagram Code
[go]$$Bcm17 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . 5 3 X . . |
$$ | . . . , . . . . . , . . . . . , . . . |
$$ | . . . . . . . . . . . . . . 4 . 2 . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X , X . . |
$$ | . . . . . . . . . . . . . . . 6 . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
Now my continuation is entirely based on the way he chooses to respond. If he blocks on top:
- Click Here To Show Diagram Code
[go]$$Bcm23 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . 3 . O X . . |
$$ | . . . . . . . . . . . . . . X X X . . |
$$ | . . . , . . . . . , . . 2 . . , . . . |
$$ | . . . . . . . . . . . . . a O . O . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . b . . |
$$ | . . . . . . . . . . . . d . . . . . . |
$$ | . . . O . . . . . , . . e . X 1 X . . |
$$ | . . . . . . . . . . . . 4 . c W . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
As the ladder starting with the cut at "a" is favourable for me, I'll probably use this as an opportunity to handle the lower side, I need to be slightly careful not to come under attack, but the immediate points value is obvious, and I still have moves like "b" to help settle the group. If he decides to look after his corner with "c", I can jump out with "d" and Black's falling behind. As a result, I expect he'll resist with "e", and after I hane, there are too many possibilities to write out. It may be that "e" should be my move instead of this

, but I'll have a closer look if

happens. If he blocks on the side:
- Click Here To Show Diagram Code
[go]$$Bcm23 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . . O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O . . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . 4 . X X X . . |
$$ | . . . , . . . . . , . . . . . , . . . |
$$ | . . . . . . . . . . . . . . O . O . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . 2 . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X 3 X . . |
$$ | . . . . . . . . . . . . . . 1 W . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
I now get

in sente, and can attack more forcefully.
The other advantage of pincering now, is the exchange that he chose not to make is now more uncomfortable for him:
- Click Here To Show Diagram Code
[go]$$Bcm17 Prisoners:

$$ ---------------------------------------
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . X . . X . 7 O . . |
$$ | . . . O . . . . . , . . . . . X . O . |
$$ | . . . . . . . . . . . . . . . . O 8 . |
$$ | . . . . . . . . . . . . . . . . O X . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . . O X . . |
$$ | . . . . . . . . . . . . . . 5 3 X . . |
$$ | . . . , . . . . . , . . . . . , . . . |
$$ | . . . . . . . . . . . . . . 4 . 2 . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . 6 . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . O . . . . . , . . . . X , X . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ | . . . . . . . . . . . . . . . . . . . |
$$ ---------------------------------------[/go]
It's hard to treat this

as entirely gote now, because Black needs his own eyespace, which may mean that

gets to be my privilege later on. Not entirely convinced of course, and vaguely suspicious that this may be overplay. I perhaps should have played O3 first and left this as a resource for later, but the fact that the bend in joseki makes me think that this may just be urgent enough to play.
Frankly, I don't have a clue
