The Cadillac Bar & Grill: Keeping a Legacy Alive

The Cadillac Bar & Grill has a long history as a social and cultural institution. It’s more than a restaurant: it’s a place where life is brimming to the top. Since the 1980s, people have flocked to The Cadillac from cities away, just to get a taste of the vivacious entertainment and authentic Tex Mex cuisine. These days however, it’s a quiet, high-ceilinged space in Mid-Market, with just owner Michael Rodriguez and a handful of employees to run the takeout and delivery service.

“Takeout and delivery has been really slow. We sit around for 8-9 hours and get maybe six orders. The business coming in from doing takeout/delivery isn’t enough to cover the expenses. I’m just hanging in there and hoping to build up a reputation,” Michael said to me. Having been in the restaurant business for over 30 years, his calm demeanor shows his experience.

“I have a lot of patience,” Michael explained. He’s had a bit of time to develop this virtue, to say the least. His involvement with Cadillac began when he was 21 years old, working for a restaurant group in Austin, Texas. Across the border in Nuevo Laredo, resided the original Cadillac Bar, which started during the prohibition. It was famous for being a drinking hole that  Americans could hop across the border and visit. Long after the prohibition lifted, the bar remained a cultural epicenter that Americans flocked to. Michael, along with colleague Jeff Warner, Bill Diaz, and financial backer Lou Miller, were intrigued by this bar. They made a deal with the owners to open up a Cadillac Bar location in San Francisco. They took certain aesthetic elements and specialty dishes with them to the South Market neighborhood, and bought a cheap warehouse near the Financial District and Moscone center.

About three months after opening in 1982, a key element changed the course of the SF based Cadillac Bar and Grill: Herb Caen. Herb was a highly influential gossip columnist for the SF Chronicle, whose work garnered critical acclaim and widespread readership, what Herb wrote could make or break a restaurant.

Herb visited the fresh Cadillac bar, headed by 21-year-olds Michael and Jeff, and praised the restaurant in his first review, saying, “It’s loud, you bring someone you don’t want to talk to, and you enjoy the entertainment.” After Herb’s sixth mention of the restaurant, lines formed outside of Cadillac’s front door for the next 15 years. Pride and a sense of “Can you believe it?” was apparent in Michael’s voice as he shared the anecdote. After years of phenomenal business, in 1999, the Moscone Center expanded, closing this social hub by power of eminent domain.

In 2015, the current version of Cadillac Bar & Grill was revitalized singlehandedly by Michael. It resides in Mid-Market, which is still stigmatized for being a more run-down area, in spite of recent renovations over the past few years. Cadillac Bar in the 80s was a place people couldn’t get enough of. The way Michael describes it, it was the halcyon days.

“That time in my life will always be embedded in me. I grew up with the staff there. We had weekly regulars we loved. People told me they met their husband or their wife there. After everything closed, we always talked about opening it again. It was always on my mind,” he said to me. Fast forward to the 2010’s when Michael reopened the bar; tech companies have flooded the neighborhood, but the tech employees don’t eat at Cadillac or any of the other recently opened restaurants. They eat at their company’s cafeterias and get their entertainment from Company provided game rooms. The business local restaurants were counting on remained insular and out of reach, forcing all restaurants but Cadillac to close.

The heady success of the 80s/90s for Cadillac isn’t the same now. Michael has steadily been rebuilding his loyal customer base. He serves employees from the nearby Civic Center and crowds who need a pre-show dinner before heading over to the Orpheum.

Michael said to me as our interview closed, “We make a good first impression. I wish people could visit us just once. If our service doesn’t overwhelm you, our food and drinks will. The area has a stigma, it’s hard to park around here, but we retain the majority of our customers. People will like what they see when they visit.” I was impressed by Michael’s confidence and the legacy he carries on. He’s seen the ebbs and flows in the restaurant business, and continues to build, hope, and dream in the midst of a global pandemic. I think it’s worth giving his restaurant a shot, don’t you?