Ben, Hurley and Locke had the deepest connections to the island. Yet, they all played the fool as their personal stories unfolded over the six seasons.
Ben had a Napoleon complex: he wanted power, control and respect as many small minded leaders throughout history have come to grasp.
Hurley had an inferiority complex: he wanted love, respect and a purpose in life but he had no drive or ambition to live his own life.
Locke had grandeur issues: he believed he had a higher calling than what society and authority targeted him for; he was a dreamer who had no skills to make his dreams come true. He had a self-destructive personality.
So why was the island's connection to these three men so strong?
The island made fools of them.
Ben worked his way up from a lonely school boy with an abusive, drunken father to a mass murderer psychopathic leader of the Others. But in the end, his loyalty to Jacob, his perceived father figure, was a farce. This led to Ben becoming a broken man.
Hurley was a lonely boy who put himself in a shell because he blamed himself for his father's abandonment. He had only one true friend, who betrayed him after Hurley kept his lottery winnings a secret. Hurley believed he was cursed by the Numbers, and that led to his growing psychological problems, including the ability to speak to the dead.
Locke was a lonely man who could not find acceptance and a real family. He bounced from odd job to odd job, to being an outcast in a commune, to a pigeon taken advantage of by others, including his own father. His desire to be a part of a traditional family structure literally crippled him, making him a bitter man who could not see the hope that Helen could have given him.
If the island was an intelligent being as many have suggested, then it used its magical resources to build up and tear down these three men. It raised up the inferiority complex Ben into a limitless, powerful tyrant, only to pull the rug from underneath his reign and give it to a real monster, MIB. Hurley's mental problems were enhanced while on the island - - - the reoccurring Numbers sounded like bullhorns in his head of his Curse. The ability to talk to dead people. And the new friends around him started to die - - - including the one woman who found him interesting. It was like he was a mental punching bag. Locke seemingly was given the greatest second chance of all time. The plane crash allowed him to walk again. He could become the outback hero on the island. He could find the respect, admiration, loyalty and affection from the castaways. He could lead them to his promised land. But Locke was merely a prop in other people's plans. When things did not go well, Locke tried to rationalize his failures as new opportunities, even though it cost him colleague's lives such as Boone. He was told that he had to sacrifice himself for the island. Martyrdom was not the goal for a young John Locke, so he balked at the notion - - - but was killed anyway. He was barely a footnote to other people because he had lived a measly, stupid life.
The island must have had a cruel sense of humor.
It gave Ben, Hurley and Locke a glimpse of what they most wanted, then tore it from their grasp.
So why would the island intelligence be so childish, so cruel?
Because it is probably a childlike intelligence. It connected to Ben, Hurley and Locke because it too was an outcast from its own society. It had the same deep, dark emotional issues of Ben, Hurley and Locke. The island could not express or vent its anger so it had to act through visitors and its smoke monsters. The island was the puppeteer who smashed its playthings together to release some of its own repressed abandonment feelings.
The island as a lonely, supernatural child lost in space, trapped in the Earth's gravitational pull, is an intriguing side story. Could it be the last of its kind? Could it have been abandoned by its parents or world much like the origin story of Superman? How could such a being with immense power want to hide in plain sight instead of ruling an entire planet? It may have never been instructed on what to do - - - or it was told about certain rules to follow. Or, worse, it was trapped in island form and unable to make a physical transition to our world. That could be just as frustrating as what was going through the minds of Ben, Hurley and Locke.
And this can explain why many aspects of LOST have a theme of cruelty. Unsupervised children often can be cruel, in their play and their outlook on life. A magnifying glass to burn ants may have been a human curiosity, but an island superbeing doing the same to human adults is another thing.