New Holiday Musical Will Warm Spirits in the Third Ward

A Gift of the Magi. Image courtesy of Milwaukee Chamber Theatre.

Searching for a bit of wintertime cheer? Or perhaps a lesson of love? Milwaukee Chamber Theatre has you covered this holiday season.

For the first time, on Nov. 14 at 8 p.m., the popular Historic Third Ward theater company is set to premiere A Gift of the Magi, an original Christmas musical by James DeVita and Josh Schmidt, based on the 1905 short story by O. Henry.

Set in bustling New York at the turn of the 20th century, “A Gift of the Magi” follows Della and Jim, impoverished newlyweds dedicated to finding the perfect Christmas gift for one another. The musical includes 25 original songs, composed by Schmidt, a UW-Milwaukee alum who received a Tony Award nomination in 2026 for best sound design of a play.

Dimonte Henning, a Milwaukee-based actor, producer, director and educator, landed the lead role of Jim. In a conversation with Urban Milwaukee, he said the show is a good reminder of what’s truly important: love.

“Love is a universal language. We all have, hopefully, experienced some form of love, connection or belonging. That’s what makes this show relevant today,” he said. “It’s not always about what you have, but about what happens when you lose what you have; about what happens in your connections with loved ones.”

Of the show’s relevance in Milwaukee, he said, “To have a story that is as universal as love be told by an all-Milwaukee, local cast and crew is great because we are the same people who live in the community. You may see us at the grocery store or at a basketball game, and at the same time, we are artists telling a story at a local organization that pours into the city and its people.”

A live violin and cello score performed by musicians Susan Nicholson and Sky Yela will join the performers onstage, which is a unique aspect of the show, as orchestras typically perform a musical’s score in a tucked-away stage pit.

“The music is especially ingrained in this show,” said Henning. “There are moments where the artists and the actors interact with the musicians. They help uplift the storytelling; some of them even sing.”

Henning said he’s drawn to Jim as a character because Jim is sensitive and deeply in love with his wife.

“I have played a lot of characters who are very macho, strong-willed and hard on themselves. Jim is not like that, so I get to tap into another level of sensitivity, of charm, of love that I don’t often get to play,” he said.

Della will be played by Jamie Mercado and O. Henry will be played by Jonathan Gillard Daly. Alexander Coddington and Kelly Doherty are the show’s director and assistant director, respectively. Music is directed by Jill Anna Ponasik.

Performances will take place in the Studio Theater at the Broadway Theatre Center.

A pay-what-you-choose performance is scheduled for Nov. 16 at 7:30 p.m., and talkbacks are planned for Nov. 19 and Dec. 3 following the 7:30 p.m. performances on those days. An understudy performance is set for Nov. 24 at 7:30 p.m. A full performance schedule and ticket pricing can be found on Milwaukee Chamber Theatre’s website.

Run time is approximately 90 minutes. Age recommendation is 8 and up.

Henning, who was recently announced as Black Arts MKE‘s new artistic director, called the musical “a Christmas treat.” It will run through Dec. 6.

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