I was close to the deceased but didn’t really know the family. Who do I send the sympathy gift to?

According to etiquette you send the gift to the closest relative of the person who has died (i.e.: the widow or the eldest child).  It is appropriate in this case to inform the gift recipient how you were connected to the deceased.  For example, in the case of the death of a business associate you may want to send something to the widow or widower.  In your card you could say something like:
“June and I worked together closely on many accounts at ABC Inc., she was a wonderful woman and fantastic coworker.  I/we will truly miss her and send you our deepest condolences.”

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