Joseph Wood Hill built the four story Hill Military Academy on NW Marshall Street in 1900. In the 1930s, the academy constructed 13 concrete buildings on the north side of Rocky Butte (the military-style buildings can still be seen on the City Bible Church campus). The structure on NW Marshall was finally condemned as a nuisance in 1943 and demolished. The Marshall Street Professional Building and a parking lot replaced the academy.
(City of Portland Archives)
Vintage Portland 
So the county jail that was on Rocky Butte took over the military school’s buildings?
Chuck – It’s my understanding that Rocky Butte Jail was built on the southeast flank of Rocky Butte. It was directly under the present-day I-205 about at the end of Thompson Street and was accessed from Hancock. It was demolished to make way for I-205 construction.
Now that I think about it, it seems like we only visited Rocky Butte at nite and I’m not sure what side of the butte we were on. I just remember those buildings that looked like fortresses. Did they close down RB Jail when the new Justice Center was built downtown? I remember its being built but can’t remember exactly when.
I’m a little late to this discussion but just a point of clarification on the history of I-205 / Rocky Butte Jail.
The jail actually stood through construction of I-205 and was located just to the east of the freeway on the south-east side of Rocky Butte (in the area between I-205 and I-84). Closing and tearing down the jail had to wait for the Justice Center downtown to be built which was set for late 1983.
At the time that section of I-205 was essentially complete, in early 1983, there was a little controversy over whether I-205 would be allowed to open before the prisoners were moved. I was in 7th grade at the time and remember we all thought it seemed a little silly to hold up opening the freeway because of worries about disturbing the prisoners. Not sure how they resolved it, but I believe that last section of I-205 did end up opening in March 1983 well before the Justice Center was set to open so I guess they decided the prisoners could live with the noise for a few months. 🙂
Once the Justice Center opened and the prisoners were moved, the old jail was demolished, but it did briefly coexist with I-205 (I believe parts of the complex were demolished to make room for the freeway but the stone fortress like jail proper was not).
Anyway here’s a quote from a story in The Columbian about the opening of the Glenn Jackson bridge in 1982 that references the potential dilemma and delay over the jail:
“The stretch of freeway near the Rocky Butte Jail (near the Banfield) is not complete. That will be done before summer next year [1983], but the question of whether the freeway can open before jail prisoners are moved to a new facility in downtown Portland has not been settled.”
http://www.columbian.com/history/i-205-bridge/
Oh and this slide show has a couple nice photos of the area, pre-I-205
Click to access GoogleEarth_HistoricalPics_Comparison.pdf