Sears, Roebuck & Company
1290 Cleveland Avenue

1952-1986




Color photos by Joe Courtney from the Stephen Grooms Collection
posted on the Vintage San Diego Facebook page October 19, 2023








Two photos from Paul Bowers

An aerial looking Northwest.  The intersection of University and Normal is at the right front.  That's Mercy Hospital left of center.   The color version below popped up on Facebook on August 31, 2023.  Sorry, that's as big as I can make it.

This aerial has a nice view of the Vermont Street
pedestrian bridge, which still crosses Washington





Evening Tribune, October 7, 1952



Evening Tribune, October 15, 1952

See above aerial photos



Going Out Of Business Sale:  Evening Tribune, February 22, 1986




Evening Tribune, March 15, 1986


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(When these comments were first posted, I wasn't sure when the Hillcrest Sears opened -- JF)

I  guess I was about 8 years old when the Sears store opened, so that would be around 1951.  I was living in my grandma's house on Maryland Street and my mother, grandma and I walked across the foot bridge (over Washington St.) to the brand new Sears Store.  We were all very excited to have a big store so near to where we lived.  Later, my first nice job was at the same Sears.  I taught sewing there (from beginning all the way through tailoring).  I was 22 and very much enjoying the work I was doing -- Elaine Robinson Davis ’61

I don't have a photo, nor a "photographic memory," but I remember as a child looking at the big white round seal on the side of the Sears building and noticing the year 1952 -- Owen Western '63

It had to be opened before 1958 because I worked there.  I used to take the bus (E route if I recall) and my job was to walk around the parking lot putting flyers for Allstate Insurance on the windshields of cars.  My "office" was a stockroom behind the garden shop and God knows how I remember this, but my boss was Mr. Matheney.  Yes, Mr. Olive worked in the tool department using saws and power tools and we would often drop by to watch him work -- Ernie Cowan ’62

I know I went to the Sears in 1956, so it had to have opened before that.  I looked it up on “hillquest” and found 1953 as the year.  I have been in the DA’s Office for almost 30 years now; early on, in the 80s, I had a supervisor who wouldn’t let us make popcorn for a snack in the office, because it made the place “smell like Sears.”  Remember the popcorn?  Had to have it every time, and then so thirsty had to go to the drinking fountain which was way in the back of the store.  Anyway, I said something recently about that, and the youngsters in the DA’s Office (all young enough to be my children) looked at me with blank stares.  They really missed out.  No more popcorn at any Sears!!!!  Oh, the good old days!!!!!   Cindi Mitton Means ’68

I worked at the Sears from about 1965 to 1968 and it didn’t seem like a very new store then.  I would guess it opened in the very early 50’s – the store number was 1078 . . . if I remember correctly, the “1” indicated it was a full sized store, the “07” indicated it was the seventh full sized store built in the “8” (or western) area of the US.  Thinking about the architecture and my various memories I might even say it was built in 1951.  (I just googled Sears 1078 and see that the number has been reassigned to a store in Mesa AZ.)    Barbara Bright Wilder ’62

I’d say that the Hillcrest Sears opened in 1952 -- Gary Epstein ’64

As I recall it was about 1952 when my mother went to work for Sears and I believe it was when the Hillcrest store opened.  She didn't drive and she had to get a transfer to another bus every morning -- Jim Smith ’63

I lived on the north side of the wood trestle bridge that crossed over Washington Street.  Sears was located on the south side.  I remember crossing the bridge as early as 1954 and Sears was there then.  I believe it opened in 1953 -- Ron Fox ’62

My first paying gig was at the Hillcrest Sears demonstrating organs. I was in Junior High -- Doug Kvandal ’66

(Sixty years later Doug is still demonstrating the Hammond Organ -- JF)

I’m guessing Sears opened in 1960. I had Mr. Olive for Wood Shop at Horace Mann.  That was where I made the 18” wood sailboat that won the regatta at the small yacht basin in Mission Bay, top boat at Horace Mann Jr -- High Ron Dixon ‘64

1953 Saw Olive too! -- Mike McKittrick ’60

Thank you for posting the info for Mr. Olive. The year I had him we each "built" a three-legged coffee table made of Monkey Pod wood.   I treasured that piece for many years -- Billy Wood ’65

I was a shop student of Bill Olive in 1960, off and on, until 1963.  I taught with my hero from 1990 until he retired from Horace Mann Middle School.  He  immediately started subbing at Mann. He was always my sub teacher if I could get him.  My wife, Mary Dart and  I were with him in the hospital for days and we were with him hours before he passed. I'll say it again!! He was my HERO!!! -- Lee Cook ’66

Mr. Olive had a side job demonstrating table saws at the new Sears. My family would always stop by the tool section to say hello. He always was happy to see us and always was making something with the saw.  Great teacher and great person! -- Russ Flynn ’64

I took wood shop from Mr Olive and we made a lamp. His teaching saved me money when I was a single mom and needed to replace the light sockets in lamps. In fact I have one right now I will be repairing soon.  He is the ONLY teacher I remember from Horace Mann -- Aletha McGregor Dellamo ’60

Our Wood and metal shop teacher at Horace Mann was Mr McLaughlin. He was also at Crawford as teacher and advisor. A great teacher and friend to all -- John Blackwood ’59

I had Mr. Olive in the early 1970s at Horace Mann.  I still have this fish I made in his class so many years ago.  Mr. Olive was a fantastic teacher and I have thought about his classes many times over the years -- Carl Spier ’75

Thanks for the Sears page. Like so many Crawford kids, I learned to drive in the Sears parking lot on Sundays when it was empty.  What a great memory! -- Wendy Williams ’76  

Well, they did have 8,000 parking spaces -- JF

I was in Mr. William Olive’s wood class.  He taught us how to make a sailboat. It was a good class. Very complex.  However, he put the keel at the front of the boat to make it more modern.  He never tried to put it in the water.  I found it just sailed in circles.  Remember to try something before you give a class -- Mark Torbert ’62

Thanks for the link to Mr. Olive's obit.  I would often see him with his troop at the district camporees.   The first day of his mechanical drafting class, he told us that the work we did fulfilled the requirements for the drafting merit badge.  Other teachers as well were aware of merit badge requirements.  I got woodworking from Mr. Howland, metal working from Mr. Hook, music from Mr Mentze, and public speaking from Mr. Meeks -- Joe Dyke '65

I remember sears, my parents would take us with them and my sisters would be taken to the TV section and watch TV until my parents would get there business -- Ted Hazlewood '63

The picture of Mr. Olive brought back so-o-o-o many memories. He was my wood shop teacher at Horace Mann back in '68. Could you find out the Metal Shop teacher from that year? For the life of me, I can't remember his name and I don't have a Mann yearbook to look him up. Thank you and I really look forward to your emails every Friday. It's kind of cool taking a stroll down memory lane -- Dan Chesser ’72

Ron Jagodinski's "Olive-18" sailboat

Mr. Olive's Obituary