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The Gail Rich Awards, "recognize select individuals who inspire our diverse and culturally-rich community." The awardees are generally local artists, but on occasion business owners are recognized. Gail Rich was a writer with the Santa Cruz Sentinel and a classical music programmer at KUSP. Each year's awards are determined by the Cultural Council Associates, and the awards ceremony itself is produced by the Cultural Council of Santa Cruz County, the Santa Cruz Sentinel, and Kuumbwa Jazz.
- I.B. Bayo (Textile Artist / Fashion Designer)
- Janet Fine (Mixed Media Artist / Photographer)
- Paul Fleischman (Children’s Book Author)
- Steve Palazzo (Musician / Guitar Teacher)
- Cathy Warner (Theatrical Teacher)