Maui Arts & Entertainment

MACC announces Schaefer Portrait Challenge 2025 award winners

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Inaugural Gene Freedman Artists’ Choice Award-winner (left) Damian Smith, “Ali’i of Ho’okipa,” oil on canvas; Ruth Freedman People’s Choice Award (right) Jett Green, “Lili’s Gift, the Beauty of a Lifetime,” oil on canvas. Photos by Jose Morales

Maui Arts & Cultural Center has announced the winners of the Ruth Freedman People’s Choice Award and Gene Freedman Artists’ Choice Award for Schaefer Portrait Challenge 2025. Each of the two awards carries a $5,000 cash prize made possible by the generosity of the Eugene and Ruth Freedman Family Foundation, with the awards presented by Rick Freedman and his sister Penny Freedman at a recent reception.

Artist Jett Green of Maui received the Ruth Freedman People’s Choice Award, determined by the popular vote of gallery visitors, for her portrait, “Lili’s Gift, the Beauty of a Lifetime,” depicting Maui resident Lili Townsend.

Gallery Director Jonathan Clark states, “Jett’s painting engages the viewer with striking photorealism in the features of Lili’s face, surrounded by a fantastical menagerie of colors and symbols that speak to her vibrant personality and the stories of her life’s journey shared between portrait sitter and artist. The portrait has a magnetic quality to it – we’ve seen visitors entranced by Lili’s gaze each day in the gallery.”

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Green studied illustration at Art Center, College of Design in Pasadena before embarking on a career in Hollywood. For several decades, she worked as a matte painter for special effects and sets in over 50 films. She moved to Maui in 2020 to focus on her passion for oil painting and currently exhibits at local galleries.

The first runner-up for People’s Choice votes was Maui artist Damian Smith for his painting, “Aliʻi of Hoʻokipa,” while second runner-up position went to Maui artist Jennifer Owen for her ceramic self-portrait, “Free.” The People’s Choice Award has been a fixture of Schaefer Portrait Challenge since its inaugural edition, and visitors to the gallery between Jan. 14 and March 14 had the chance to cast their ballots for their favorite piece in the exhibit. Over 5,000 visitors have come through the gallery doors to see this exhibit.

The Gene Freedman Artists’ Choice Award represents a new addition to Schaefer Portrait Challenge, with the award selected by the collective vote of all forty exhibiting artists. The inaugural recipient of the Gene Freedman Artists’ Choice Award is Damian Smith of Maui with his work “Aliʻi of Hoʻokipa,” portraying John Kalei Matthew Hoʻopai.

  • Damian Smith, winner of the Gene Freedman Artists’ Choice Award for Schaefer Portrait Challenge 2025, stands with portrait subject John Kalei Matthew Hoʻopai alongside his winning piece, “Aliʻi of Hoʻokipa.” Photo by J. Anthony Martinez
  • Jett Green, winner of the Ruth Freedman People’s Choice Award for Schaefer Portrait Challenge 2025, stands with portrait subject Lili Townsend alongside her winning piece, “Lili’s Gift, the Beauty of a Lifetime.” Photo by J. Anthony Martinez
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“Damian honors his subject Kalei, illuminated by the golden light of sunset at his familiar Hoʻokipa pavilion seat and flanked by an expansive panoramic composition of the North Shore that intertwines both person and place,” Clark said. “A frequent plein air painter, Damian worked on this three-panel painting on-site at Hoʻokipa over the course of the summer, getting to know Kalei through talk story, shared meals and surfing.”

Damian Smith is an oil painter and former professional skateboarder originally from Philadelphia. He studied at Studio Incamminati in Philadelphia and has exhibited in both Pennsylvania and Hawaiʻi. He received First Place in the 157th Annual Philadelphia Sketch Club Small Works Show in 2020 and Award of Excellence at the 2018 Rittenhouse Square Fine Art Show.

The first runner-up for Artists’ Choice nominations was Kauaʻi artist Penny Nichols for her mixed media portrayal of her two sons in “All This Time,” while second runner-up position again went to Maui artist Jennifer Owen for “Free.” Artists were given ample time to consider which of their exhibiting colleagues to nominate for this distinction.

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The Jurors’ Choice Award winner was announced in January 2025.

Schaefer Portrait Challenge is a triennial statewide juried art competition and a signature exhibition of Schaefer International Gallery since 2003. This marks the eighth edition of the Challenge, featuring 40 artists from across Hawaiʻi whose works in portraiture were selected by jurors Sonnet Coggins, Mina Elison and Wendy Kawabata.

The exhibition continues in Schaefer International Gallery at Maui Arts & Cultural Center through March 22, Tuesday through Saturday, 10 a.m. – 4 p.m., and also before select Castle Theater shows.

After its conclusion on Maui, the Challenge will be traveling to its next venue. Maui Arts & Cultural Center is pleased to be partnering with the Hawaiʻi State Foundation on Culture and the Arts to travel Schaefer Portrait Challenge 2025 in its entirety to Oʻahu for exhibition at Capitol Modern: The Hawaiʻi State Art Museum. The exhibition is currently slated to open at Capitol Modern in January 2026 and will remain on view for the first half of next year.

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