The Sentinel

I'm a big fan of working from home--not only is every day casual Friday, but there's no line to get my morning macchiato--and if the barista happens to be copping attitude, maybe it's because she was out late and is feeling a little cranky. And when it's lunchtime, I get to make my sandwiches just how I like 'em (yes, I have a panino press and I know how to use it). And I get to eat lunch in my slippers. (Only my UPS guy and I know what color they are.)

So when I find myself occasionally downtown at high noon, it's a big whirlwind of lunch-getting activity I forgot about. Heck, it's been eight years since my ad agency job on Spear Street. In those days I occasionally made runs to the spendy salad bar at Lightening Foods, but I preferred to make my sandwiches instead, like spicy coppa with melted provolone and artichoke hearts on rosette rolls from Il Fornaio. My boss even offered to pay me each week to make sandwiches for him, but I was trying to be known as a copywriter around the office, and not the sandwich maker.

Prior to that, I remember working on Maiden Lane, and being a broke-ass 20-something, I'd suffer the multitude of sandwich abuses at Lee's (both ordering and consuming abuses)--but I will say my custom combo of egg salad and olive salad was pretty rockin'. Just the same, those were the dark sandwich years.

And now, the light. I have tried to make my way to Dennis Leary of Canteen's ~THE SENTINEL~ at least four times. It has been shining its beacon for months, but either the line was way too long, or my lunch date had to cancel, and finally, finally, I was downtown last week and got to try the famed sandwiches with a pal.

Since this place is take-out only, and I don't have an office desk around the corner where I can sit and eat, I had to hunt down a sunny little spot to scarf my sandwich. On a rainy day, maybe someone will rent me his or her desk for ten minutes?

The menu is posted online daily for those of you who want to start salivating early, or call your order in. It definitely reads like food porn: smoked trout with fennel, apple, horseradish cream cheese, or how about turkey meatloaf with cranberries and chipotle? You know you want the chocolate chip walnut cookie.

The line was about ten people deep, but moved impressively quickly. Some folks try to get there early to beat the line, and get their pick of the litter before anything runs out. Inside, the staff is hustling. Dennis Leary, the powerhouse for this outfit, is behind the counter daily, moving intently like the prizefighter of sandwiches. I just hope he doesn't give himself a coronary before he's 40--the guy is like a downed power line, rippling around with an intensity that makes you keep your distance. I've never seen him stand still.

I do say bless him: not only is he supplying the city with some of the tastiest breakfast treats and sandwiches, but he's also taking a stand on sandwich preparation, stating on his menu that "all of our sandwiches have mayonnaise, please specify if you don't want it," and "no more tomatoes until next summer, sorry!" So fuhgettaboutit! Love it.

While you're waiting outside, the smell of baking bread starts tempting you. No, it's not from a ubiquitous Subway, with its tacky bread smell. This is more like mmmmm mmmmmm good bread smell. Real bread.

The flatbread on my corned beef sandwich ($8.25) was most definitely mmmmm mmmmm good--perfect texture and flavor, just-right oiliness, and it held up like a champ. Now, the corned beef is not like a mountainous deli sandwich from Millers East Coast West that you can hardly get your mouth around, or finish eating. This is more like a classy California sandwich, with just enough meat. Juicy meat, too. The kick of Gruyere, crisp shreds of cabbage, and bright Russian dressing made this sandwich an ace. You can taste everything, and you can taste it all come together. Oh yeah, and the pickle on the side had a good homemade tang, but wasn't too sour.

At first, I thought the sliced pork loin ($8) with fig jam, frisee, and manchego was too sweet--I wanted something to counter it, like some mustard vinaigrette on the frisee. But that's just because I was still immersed in my corned beef sandwich--there was no competition. Once that half was done, it was time for meat dessert, which the half of pork loin sandwich fulfilled.

Unfortunately, the yellow lentil curry soup was a disappointment--I couldn't detect any curry, and it was thin and watery. It was like having expensive gruel ($5.50). Not a good soup day. Although the little wedge of bread was a nice touch. Wasn't super thrilled with the pomegranate-lemonade ($3) either, it was just kind of meh--it's like the flavor was still asleep and hadn't woken up yet.

I did appreciate the little touch of the complimentary Andes mint in the bag (totally brought me back to my childhood--we used to have a bowl of these at the counter of our deli), and the eco-friendly packaging and silverware is right on. A friend who works in the area is all cracked out on the homemade muffins that come with fresh fruit in them--she also likes the coffee a lot.

And then there's the look! It's vintage cigar shop (its previous incarnation) meets sandwich shop, with an on-point 1940s East Coast vibe, an old school cash register, cigar boxes for napkins and tips, gleaming subway tile, and the biggest pepper mill I've ever seen. Not sure about that--maybe it's a totem pole for a sandwich shop that kicks butt?

The Sentinel
37 New Montgomery
Cross: Jessie St.
San Francisco, CA 94105


Mon-Fri 7:30am-2:30pm

Sandwiches $8-$8.50
Desserts $2.50

A few tablehopper readers wrote in some ideas for where to eat your Sentinel sandwich! Check this out:

I recommend one of the two lovely public rooftop gardens accessible from Crocker Galleria across Market. The nice one on the corner of Post/Montgomery/Market (over the gorgeous old Wells Fargo bank) has a prominent entrance from the top floor of Crocker Galleria. If it's raining, you can snag a table inside Crocker Galleria. Or go to the inside public space around the corner from Sentinel at 55 Second St.

There's a smaller, more hidden rooftop garden that faces Sutter and the historic Halladie building. From the top floor of Crocker Galleria, go to the unmarked staircase in the NW corner of the building and go up. It's also accessible from the Galleria Park Hotel. Excellent for good weather days when everywhere else is busy.

343 Sansome Street is another place with a beautiful rooftop deck that is open to the public - great for taking your own lunch from Sentinel or elsewhere.

And one more tidbit I plan to put to use: the groovy folks at REBAR have even created an interactive map of downtown privately owned public open spaces, check it out here.

37 New Montgomery San Francisco
(at Jessie St.)
Dennis Leary, chef


  • Sandwiches


  • Breakfast
  • Lunch

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