It was all captured in a cell phone video that went viral.
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Now, Drew may have a place to live.
He told me his name is Greg, but most everyone calls him Drew.
He's become a permanent fixture at the Pergola at Lake Merritt. People seem to have gotten used to looking at a pile of his belongings stashed in one corner.
It was a cell phone video taken several weeks ago that shed light on his situation when a man was caught trashing his stuff.
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Outraged, some in Oakland decided they could no longer stay on the sidelines. A GoFundMe page was set up that raised $14,000.
"We're not taking donations at this moment. The reason why is because we...have found an apartment for Drew," said Kenzie Smith, a community leader.
While noble, is that practical? During our conversation with Drew, he assured us he did not have mental health issues.
"If you have mental well wishes, if you mentally think good thoughts, you can project good thoughts," Drew said.
Wendy Jackson is the executive director of the East Oakland Community Project, which helps homeless individuals and families.
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"His community is already a resource, but it sounds to me like from what you've observed he needs an assessment around his ability to sustain himself in housing,"Jackson said.
She promised to get in touch with those helping Drew to try to get him the support he needs to finally get out of homelessness.
People who often see him say it's a complicated fix.
"It's complicated because you have what you think is that person's best interest, which might be separate from what that person feels is in his or her best interest," said a man who did not want to be identified.