In a heartwarming celebration of the holiday season, Chicago’s South Side became a beacon of generosity and joy on Christmas Eve. Hundreds of toys, clothing, and various gifts were distributed to local families, bringing smiles to the faces of both children and adults.

This event, one of the largest giveaways in the city, is a cherished annual tradition. Families eager to participate can sign up via social media or by sharing their stories, ensuring that each child receives the opportunity to select three toys. The only stipulation is that a child must accompany the family to participate, making the experience even more personal and special.

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The simple joys of a picture with Santa, a cozy new coat, and a shiny toy are often taken for granted by many. Yet, for countless families across Chicago, such delights are made possible only through the kindness of others. This year, the gathering took place at the National Association of Letter Carrier’s building in Bronzeville, where instead of mailing letters, families wrote to Santa and had their wishes granted on the spot.

Juanita Harris, one of the many attendees, was there with her two grandchildren. “These two kids have only their mom and, of course, grandma when I can help,” Harris shared. “This event means a great deal to their mother, providing a little relief during the holiday season.”

The selection process for the giveaway included reading the heartfelt stories submitted by families. These shared experiences highlight the community’s spirit and the significant impact such events have on those who might otherwise go without.

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.”

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.