Chicago Shakespeare Theater's 40th Anniversary Gala Raises $1.3 Million

Chicago Shakespeare Theater celebrated the company's 40th Anniversary with the Revel in Ruby Gala on Friday, June 12, 2026. The evening raised $1.3 million, honoring four decades of powerful theatermaking and fueling the artistry, education, and community engagement that have come to define CST. 350 attendees from Chicago's civic and cultural community gathered for a lively cocktail hour and seated dinner with a program in The Yard, followed by desserts and dancing in the Jentes Family Courtyard Theater lobby.

The 2026 Gala was co-chaired by CST Board Members Steve Brodsky and Carole Segal, and the committee included Brayton Alley, Jillisa Brittan, Kate Blomgren, Liz Brodsky, Aaron Hoffman, Judith Loseff, Richard W. Porter, Lance Richards, Steve Solomon, Jamie Stone O'Brien, and Donna Welch.

During the event, CST presented the Spirit of Shakespeare Awards, honoring those who embody Shakespeare's spirit through community engagement and artistic leadership, to five new recipients:

Artistic Honoree Kevin Gudahl is an award-winning Chicago actor. He holds the record for appearing in 65 CST productions, including 53 as an actor and 12 as verse coach or director. Memorable roles include Dromio in The Comedy of Errors (2008 & 2023), Duke Senior/Duke Frederick in As You Like It (2021), Winston Churchill in The King's Speech (2019), multiple roles in the two-part history cycle Tug of War: Foreign Fire & Civil Strife (2016), William Shakespeare in Elizabeth Rex (2011), Buckingham in Richard III (2009), Fredrik in A Little Night Music (2003), Brutus in Julius Caesar (2002)—as well as the title roles in Anthony and Cleopatra (CST's inaugural Navy Pier production in 1999), Romeo and Juliet (1993 in Grant Park), and Macbeth (1992).

This year's Civic Award recognized Gary Gerst, William R. Jentes, Raymond F. McCaskey, and Pam Walter for 30 years of continuous service to Chicago Shakespeare's Board of Directors. Gary Gerst is a founding partner and former Co-Chairman and Chief Executive Officer of LaSalle Partners (now JLL – Jones Lang LaSalle Incorporated). During his tenure as Chair from 2008–2010, the theater was honored with the Regional Theater Tony Award and made its Edinburgh Festival Fringe debut. William R. Jentes was a principal litigating partner at Kirkland & Ellis for close to 30 years. Jentes played an active role in bringing CST to Navy Pier as co-chairman of the Facilities Committee (along with Gerst) and was particularly proud to lend his family's name to the Jentes Family Courtyard Theater. The Award was presented to Jentes in memoriam and accepted by his daughter Justine Jentes. Raymond F. McCaskey was formerly the Chief Executive Officer of Health Care Service Corporation, better known in Chicago as Blue Cross Blue Shield of Illinois. As Chair from 2010–2013, McCaskey oversaw CST's 25th Anniversary Season and Silver Jubilee Gala, featuring the inaugural Spirit of Shakespeare Awards. Pam Walter's legal career began at Gardner Carton & Douglas, where she worked for decades, through two firm mergers and changes of name, until she retired from Faegre Drinker Biddle & Reath in 2021. During Walter's tenure as Chair from 2004-2006, the Theater celebrated its landmark 20th Anniversary Season and increased its institutional profile around the world with its Off-Broadway debut and Royal Shakespeare Company debut.

During the cocktail reception in the Theater's lobbies, artists in lavish costumes from past CST productions mingled and posed for photos with guests, alongside lush floral arrangements from Pollen. Guests then transitioned into CST's largest venue The Yard, decked with grand spectacle and floating chandeliers, for a seated dinner and program. The program included remarks from CST founding Artistic Director Barbara Gaines, and performances from actors Bruce A. Young (who spoke the first lines in CST's inaugural production of Henry V at the Red Lion Pub in 1986), Katy Sullivan (Tony Award nominee who played the title role in CST's 2024 production of Richard III), Jaylon Muchison (acclaimed Chicago actor who played the title role in this year's Short Shakespeare! Hamlet), and Kevin Gudahl (Spirit of Shakespeare Artistic Award recipient). The evening also included a performance of “It Don't Mean a Thing” from CST's upcoming production of Play On!, with vocals by Lorenzo Rush Jr. and accompaniment by Beckie Menzie, and a performance by Chicago Public Schools' Senn Arts High School of a scene from Hamlet, which won this year's Chicago Shakespeare SLAM.

Attendees enjoyed a three-course dinner from Catering by Michaels paired with wines generously donated by Flickinger Wines. To cap the night, guests pledged direct support to Chicago Shakespeare's education initiatives during a paddle raise.

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