Because he is just like Vice President Cheney, only smarter.
You are focusing too much on the word “pirate.”
These pirates, fisherman, smugglers, sailors, what ever you want call the people operating boats out of ports on the Somali coastline, have known, well-publicicized ties to Islamic Extremists, many of who have publicly stated support for Al Quaeda. As a group they constitute an ideal intelligence gathering service.
If they are capabale of smuggling guns, drugs, fish, ipods, anything back and forth don’t you think it is logical that they would also be capable of smuggling people? In fact, they are known to have smuggled people, so the answer is obviously: Yes.
These conditions would make it easy for anyone, with any purpose, to travel by ocean between the Middle East and East Africa. Look at the map. With a small boat, which are nearly impossible to detect, you could make the journey in about 36 hrs.
It is even easier for Bin Laden because many of the Somalian people, if they are educated enough to even know who he is, respect and/or fear and/or love the maniacal bastard. If they don’t they are afraid of someone who does.
These same people have better information about Navy Patrol patterns, weather conditions, etc. in that waterway than anyone. They need to have it to survive. If they didn’t have it they wouldn’t be Pirates anymore, they would be dead piractes, or prisoners.
From Osama Bin Laden’s standpoint, this is an ideal motivation for an ideal intelligence gathering service.
He send people to test the routes before he tries them and punish people for bad information if he is so inclined. He can also excahnge their reliable information for misinformation if he chooses to.
Bin Laden is a gifted strategic thinker, and access to both East Africa and the Middle East is crucial for maintaining whatever control he still has over various terrorist networks. These people generally operate with face to face meetings. He needs to be able to get back and forth so he can talk to people face to face if he wants to maintain his grasp on power. Fear of losing this grasp motivates Osama more than any other concern. In this sense he is very much like our former Vice President.
The US Marines are currently pushing towards the Panshir Valley. Many of them expect to find Bin Laden there. They won’t find him there because he isn’t stupid enough to stick around with a bunch of Jar Heads bearing down on his position. He probably left before they arrived.
Like Cheney he is motivated more by a desire for power than any ideal. The power he is seeking is power over the people in the Middle East. Attacking America was just a means to that selfish end.
When any military tries to attack Somalia the people there fight back. They are defending Bin Laden’s position whether they realize it or not, which is even more ideal for him because it means that it is impossible to capture these people and get any useful information out of them. They don’t know he is there, and they certainly don’t know where.
By invading Iraq the Bush Administration played right into Bin Laden’s hands. &n bsp;Bush and Cheney did exactly what our enemy wanted to them, and then used this as evidence of their heroism. I believe Bush was actually foole, but Cheney knew this all along and didn’t care. For Cheney 911 was a political opportunity to practice the politics of fear. The Congress, and the Press, collectively, fell for it.
In some parts of the Middle East, incidents as horrible as 911 happen every day. The death toll may not be as high, but to the people who witness them, who are maimed, or killed, or have family members or friends who are maimed or killed, the psychological effects are the same.
To many who live in these places, in a culture that values personal courage over almost any other quality, we not only looked like cowards, but our national principles looked meaningless.
President Bush is largely to blame for this because in the end it was his responsibility to uphold our national values. He failed miserably while the world watched. This is not a very good strategy for spreading the values of Democracy.
Osama sent a dozen men onto airplanes.  Bush sent most of our Military Forces to a country Bin Laden cares nothing about, and in the process made Osama Bin Laden into what he is today, a hero to fanatical Muslims.  This is precisely what Osama Bin Laden DOES care about.
