Free Christmas toys Chicago: Hundreds of families receive gifts at annual I Am A Gentleman toy giveaway on Christmas Eve
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In a heartwarming display of holiday spirit, hundreds of toys, clothing, and other gifts were distributed on Christmas Eve on Chicago’s South Side, bringing joy to many families in the area.

This annual event stands as one of the city’s largest charitable giveaways. Families eagerly register online or share their stories to participate. Each child attending the event is allowed to select three toys, with the only stipulation being that a child must be present for the family to join in the festivities.

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For many children, moments like taking a photo with Santa, receiving a warm coat, or unwrapping a new toy are cherished traditions. However, for numerous families in Chicago, these experiences are made possible only through the generosity of others.

On a chilly Wednesday, several families gathered outside the National Association of Letter Carriers in Bronzeville. They weren’t there to send letters but rather to pen wishes to Santa that were swiftly granted, thanks to the efforts of the I Am A Gentleman organization. Among the crowd was Juanita Harris, accompanied by her two grandchildren.

“These two kids have just their mom and, of course, grandma when I can contribute,” Harris remarked. “This event is a tremendous help for her.”

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Many of the families participating in the giveaway were selected after writing in with their stories.

After taking their pictures with Santa, each child was given the opportunity to pick out three toys. There were also bags of groceries with all the essentials for Christmas dinner, and new coats and gloves for those who need them.

“This is a perfect event,” father James Powell said. “I appreciate this with all my heart.”

Many of those on the giving end are participants in I Am A Gentleman’s male mentorship program. Ty’Shaan Williams, 17, is in his first year with the organization.

“This is my third year, back to back to back,” Williams said. “I’m going to come back here every year, even after I leave I Am A Gentleman. I’m going to come back here. It’s an amazing experience.”

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That is exactly the purpose of I Am A Gentleman, to take young Black inner-city youth and turn them into leaders within their community. The Christmas giveaway is the way they close out a year of activities.

“These young men are taught what it means to be productive citizens of their communities,” said Jermaine Anderson with I Am A Gentleman. “They’re part of our 14-week program learning various life skills, but every Christmas Eve, they suspend everything they have going on to serve others.”

The event has replaced what used to be I Am A Gentleman’s home visits from years ago, but that doesn’t mean they don’t still make house calls, or hospital calls. One was planned for later Wednesday at Comer Children’s Hospital.

“We’re bringing Christmas to Tamari,” Anderson said. “Not only are we bringing Tamari his favorite characters from Paw Patrol, but we’re bringing Christmas dinner for that family right where they are.”

I Am A Gentleman’s Christmas giveaway is in its 11th year and each year it gets bigger, with some 300 families participating in the event.

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