Chicago Bears QB Caleb Williams turns head away from NFL

Imagn Images

Chicago Bears QB Caleb Williams turns head away from NFL

Originally posted on ChiCitySports | By Paolo Songco | Last updated Apr 28, 2026 7:28 PM ET

Chicago Bears quarterback Caleb Williams drew significant attention on Saturday during the closing rounds of the 2026 NFL Draft. Instead of focusing solely on the league’s new arrivals, Williams watched a National Women’s Soccer League (NWSL) matchup.

The Bears star spent the third day of the draft supporting Boston Legacy FC in its game. The Chicago Stars FC hosted the match at Northwestern Medicine Field in Geneva, Illinois. Williams currently serves as a high-profile investor for Legacy, a role he assumed in October 2025.

The 24-year-old quarterback manages his sports investments through 888 Midas. It is the strategic firm he founded in 2024 that provides a platform for athlete-led private equity and venture capital. William’s commitment to the Boston club highlights a growing trend of professional athletes supporting the future of women’s sports.

Jan 18, 2026; Chicago, IL, USA; Chicago Bears quarterback Caleb Williams (18) looks on during warmups before an NFC Divisional Round game against the Los Angeles Rams at Soldier Field. Mandatory Credit: David Banks-Imagn Images

Chicago Bears: Caleb Williams supports women’s soccer

On Saturday, the Chicago Stars posted an Instagram photo of Williams standing on the field between officials from the two teams. Both women wore scarves from the Chicago and Boston squads. The image showcased the NFL star’s involvement with both cities.

“Chicago Boston Caleb Williams is all in on women’s soccer!” The Stars captioned the post.

View this post on Instagram

A post shared by Chicago Stars FC (@thechicagostars)

The post turned heads, with fans flooding the comment section with enthusiastic comments about Williams.

“Love how you are going to games more and more,” a fan commented.

“If Caleb likes Boston women’s soccer so do I,” another fan wrote.

“The only iceman I know

️,” a supporter posted.

“The GOAT ,” another comment read,

“Man of the people,” a supporter remarked.

“That’s my qb1 ,” one more fan said.

Despite the support from their high-profile investor, the Legacy suffered a 2-0 defeat against the home team. The loss marked the fifth consecutive defeat for the winless Legacy.

The club currently sits at the bottom of the NWSL standings as the only team without a victory this season. Williams witnessed the struggle of his investment firsthand as the home crowd celebrated Chicago’s dominant performance.

Williams is a former Heisman Trophy winner and the number one overall pick from the 2024 NFL Draft. Since then, he has transitioned from a collegiate and NFL star to becoming a business mogul.

The quarterback’s presence at the NWSL game highlights his role as a strategic team owner. It also shows his strong connection to Chicago while he stays professionally linked to Boston.

Williams is now entering his third season as the face of the Bears franchise. As he prepares for the upcoming NFL season, he is also focused on elevating the profile of women’s sports.

Williams proves that modern athletes can excel on the field while successfully managing diverse business ventures.

This article first appeared on ChiCitySports and was syndicated with permission.

More must-reads: