Now president and general manager of WGN-AM (720), the fast-talking, f-bomb-dropping radio impresario — who helmed WLUP-FM (97.9) “the Loop” during its 1980s heyday — made a vast fortune when he sold his company, AM/FM, Inc., to Clear Channel Communications in 2000. But while these days he’s shedding material possessions (and would like to shed some weight), his drive to succeed and passion for people haven’t waned.
I don’t want a younger audience for ’GN. I want 35- to 65- or 70-year-old people.
I’m never telling my age, so don’t ask or I’ll kick you in the stones.
People would say, “Whoa, now you have a sports station [FM-87.7]. Isn’t the Score [WSCR-AM 670] your enemy?” No. I started in the business with [program director] Mitch Rosen. And [CBS Chicago radio boss] Rod Zimmerman, I play golf with him all the time. Do I want to bury ’em? Hell, yeah. I wanna kill ’em.
I’m not spending a nickel [at WGN]. All the people writing that I’m spending all this money have no f—— idea what they’re talking about. None.
Economics are report cards to people. How much do you make? How much stock do you have? That doesn’t matter to me anymore, because I’ve played the game.
It isn’t about money. It’s about people. It’s about doing something that you really care about.
I don’t have one contract with one person on our station. Not one. They’re all here because of how they feel. Any time they want, they can walk out the door.
I grew up [in Montclair, N.J.], having everything, losing everything, having everything, losing everything, with a lot of craziness in my life.
My mother was very ill. It was a long, very difficult medical situation. My father was a big-time attorney. He was a macher, a rainmaker. He drank. Ended up drinking himself to death. They died four months apart. I was 15.
That made me have to go out and fight for it, because I had nothing.
Money isn’t a driving factor for me, because I’m old — I’m done. Money never makes you happy. It corrupts people. It makes you weird.
Your ego drives you to do silly things.
Now I’m trying to learn to say, “Thank you, that’s a really nice compliment.” [But] I won’t go home and sit around going, “Wow, hey, I’m great.”
I’m smarter [now]. Way less ego-driven.
A good friend of mine said to me, “Deacon, from [age] 0 to 30, we’ll live anywhere, work anywhere, do anything, sleep anywhere, travel on a dime. [From] 30 to 60: cars, kids, planes, houses. At 60 until the day you die, you want to just get rid of everything you have and have your golf clubs in your truck, a pimped ride and your friends with you.”
So at 55, I started getting rid of things. It’s cathartic. It’s fantastic.
I’m in the process of selling a home on the lake, and [my wife and I] just bought a house in Northfield, which we’re remodeling. And I have a place in Palm Springs. Sold everything else. Sold the ranch, sold the ski house, sold the planes [a Falcon 50 and a Falcon 2000], sold [the home on] Nantucket.
Do you have any idea what the upkeep on a Colorado ski house is? $150,000 a year.
I can go rent the top floor of the Ritz-Carlton, get up in the morning, stand on the roof naked and burn hundreds and it would be less than heating and running the ski house.
I would say I’m a shoe whore. And I like technology.
I live comfortably. I’m not a miser. Donated a lot to my school [the University of Colorado], to Catholic Charities and have done a lot of fun things for people.
Keefer’s restaurant [in which de Castro is a founding partner] is because [co-owner] Glenn Keefer is the first guy I met here. Tavern at the Park is because my two nephews run it. Not ’cause I’ll ever make a f—–’ nickel at either place.
I don’t have stress. I think it’s because I care less. Not care less, but it’s less important. I’m not going to fail or make it based upon what we’re doing [at WGN].
I’m pretty happy. Of course I’d like to be a little thinner. Of course I’d like to have a little more time.
I’ve done the data collecting on going to Palm Springs for two months and trying to hang out there, and by the third day I’m like, “OK, I’ve played enough golf. OK, I’ve seen enough tennis. Let’s go do something.”