It’s the melancholy irony of princes: They can’t become kings until somebody near and maybe even dear to them dies. Take Kyle De Santis, for example. Until last spring the self-possessed 28-year-old was crown prince of what is routinely referred to as the De Santis “empire,” a Chicago-based corporate realm with interests in catering, real estate and live theater production. Now he has ascended the throne, which is exactly what he has wanted most. But the condition for that ascent turned out to be the loss, in quick succession, of his beloved grandfather, Tony De Santis, and his aunt, Diane Van Lente.
“It’s been an awful year,” he says, throne or no throne.
Founded in 1949 by the famously feisty Tony, the De Santis empire once extended to five Drury Lane Theatres — famous for putting on the full-glitz-press with musicals featuring major, if often slightly dated stars — and the Drury Lane Martinique restaurant in Evergreen Park. Though it has shrunk some, it still encompasses the 549-seat Drury Lane Water Tower Place at Chestnut Street and Michigan Avenue and the west suburban Drury Lane Oakbrook Terrace complex, which includes catering facilities, a conference center and a 980-seat theater.
Kyle pretty much grew up at the Oakbrook Terrace site, where Tony and grandmother Lucille maintained an apartment literally over the store. “My earliest memory is playing on the stage,” he says, soft-spoken, amiable and remarkably unguarded (the only suggestion of tension, a habit of tugging at his shirt cuff) as he perches on a chair in a small office off the Drury Lane Water Tower Place lobby. “Going through the sets, picking up the props, playing with them — even just opening and closing the fake doors and windows.
“It was always a very magical place and something that I responded to when I was little. How could you not when you’re little?”
There came a moment, though, when Kyle learned to appreciate his grandfather’s domain on an entirely different level. He was in the Oakbrook theater, watching a production of “42nd Street” with his great-grandmother — Tony’s mother — who was nearly 100 at the time. “There was a really big dance number,” he recalls, “and I looked over at her and she was crying. She was just so moved and excited that her son had created all this and was able to entertain all these people. That was the first time I realized what my grandpa did and how this affected a lot of people other than my family. It wasn’t just a playground.”
Kyle worked summers at Oakbrook throughout high school, starting in the box office and knowing “this was something I wanted to do.” He went away to college in 1996, but his divorced mother, Deborah, died unexpectedly within a month of his departure. “And that definitely changed my perspective,” he says. “I felt like I was no longer a child [and] it was better for me to come back home and start right away. … Go to school here but also be more involved in the business.”
Upon returning, he divided his days between pursuing a business degree at Loyola University and acting as his grandfather’s secretary: writing correspondence, maintaining Tony’s notebook, sitting in on meetings. Tony and Lucille, meanwhile, moved into Deborah’s Lake Forest home to help raise Kyle’s two younger siblings, Abby and Drew — in part because their father’s sales work kept him away three weeks out of each month. Though Kyle is careful to emphasize that he, Abby and Drew have a “very good relationship” with their dad, they nevertheless decided to change their last name from Koster to De Santis “just because [Tony] was always there for us.”
Tony was in his early 80s then, and still noted for his toughness. But Deborah’s death “changed him,” recalls Bill Osetek, an 18-year Oakbrook veteran who became artistic director in 2006. “He definitely softened at that point.”
Spent a lot of time together
Osetek also sees this as the period when Tony truly began grooming Kyle for succession. “I know it was happening,” he says. “You could tell by the way Tony was taking Kyle under his wing. They would spend a lot of time together.”
Apparently the grooming process was complete by the time Tony’s health took a turn for the worse earlier this year. “My grandfather was a person who never liked to give up control of anything,” Kyle says, “but in his last couple of months he started [doing so]. I was doing just about everything. … And then it got to a point where I was telling him what was going on in the business and he just shut it out. Just like, ‘It’s fine. We don’t need to talk about this anymore.’ So that was it.”
Tony died June 6. His daughter, Diane — Deborah’s only sister and Drury Lane’s longtime executive producer — died of ovarian cancer Aug. 13, at age 57. She had been sick for three years but had kept it quiet to avoid upsetting her parents. In interviews he gave right after taking charge of the empire, Kyle emphasized continuity. There would be no radical changes to the Drury Lane formula of presenting people-pleasing productions in a Victorian-music-box setting heavy with red plush, filigree and outsize crystal chandeliers. In fact, one of Kyle’s few initial deviations from the norm might be interpreted as a fuller embrace of it: The 2008-09 Oakbrook season will consist entirely of musicals, whereas Tony usually programmed four musicals and a play.
But a more significant change was under way even before the transfer of power. According to Osetek, Diane had long lobbied the bottom-line-conscious Tony to put more money into production values — sets, sound system, etc. — arguing “that the likeliest way to improve profits is to improve the quality of the show.” Kyle has taken this on as his priority, and the effects may already be evident in Oakbrook’s current production, “Meet Me in St. Louis.”
Throwing down gauntlet
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“Clearly with ‘Meet Me in St. Louis’ there has been a real dedication to the visual production,” remarks David Bell, a director/choreographer best known in Chicago for his work at the rival Marriott Lincolnshire. “The fact that they inaugurated Kyle’s first show with something so beautiful is very, very impressive and throws the gauntlet down to everyone else in the community that this is a place where good and quality musicals are going to be done.”
Drury Lane Water Tower is more of a puzzle. Reopened two years ago after Tony’s first effort closed in 1983, the Gold Coast site lacks Oakbrook’s clear identity and enviable 24,000-name subscriber list.
Fortunately for him, he has time to look. An outside production of “The 25th Annual Putnam County Spelling Bee” has vacated the space after a long run; now an outside production of “Altar Boyz” is filling it nicely and seems likely to stay for some months.
Gary Griffin has confidence in Kyle’s ability to figure it all out. A former Oakbrook artistic director who has gone on to direct some significant shows, including “The Color Purple,” Griffin has been consulting with Kyle and considers it a good sign that the young king is seeking advice “from people who know.” He also finds it encouraging that Kyle enjoys the day-to-day nitty-gritty even more than Tony did, and seems to be willing to “grow in all ways,” not merely feeding his successes.
And then, too, he thinks Kyle’s a “sharp, classy guy.” Which appears to be the case. For this interview, Kyle was dressed in a tailored, gray wool, pinstripe suit and red-and-blue Windsor-knotted tie. His loafers looked Italian. Unquestionably sharp and classy. Even regal.
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