Kankakee High School is presently located at 1200 W Jeffery ST in Kankakee, IL, but it is a 4th generation structure for the Kankakee area. The first independent high school structure was built in 1906 in the downtown area to relieve the enrollment pressures on the Central school building. That building served well for a little over 20 years, but as the area experienced rapid growth in the roaring 20's, a replacement was needed, so they chose open property about a mile east of the court house on the SE corner of (now) Merchant and Warren ST's. The second high school building was completed in 1929 and served as the city's main high school facility until further growth moved the city to build two new high schools as a replacement for the second structure. These new schools - Eastridge and Westview - served as high schools for Kankakee from 1965 until 1983. After the city experience a dramatic and traumatic downturn in fortunes, Eastridge was re-purposed to be the middle school and Westview on 1200 W Jeffery became Kankakee High School that continues to serve the city to the present. Oh, and the 1929 structure is in use today (mid-2015) under the moniker "Lincoln Cultural Center," containing offices and facilities for the school district as well as the local theater company.
This mug appears to be a commemorative for a KHS Class of 1939 50th anniversary reunion. I can find no information on the event, but I can ascertain no other reason for the 1939 date (as the school house depicted on the mug is the 1929 structure). So I'll leave the history and assumptions there and get on with the item! The depiction of the school house is from the perspective of someone standing on the corner of Warren and E Maple ST's, and DOES NOT show the addition on the south side that stretches nearly to E Maple ST.
The mug is standard-sized and looks spanking new - no, I mean it... there is absolutely NO abrasions on the raised maroon screening of the school building and writing below it. There are no marks outside or inside this cup! Perhaps it was brought home from the assumed reunion, put on a shelf, and promptly forgotten for a quarter of a century! It's in amazing shape. The printing is maroon over columbia blue, and there are no signs of cracks, blemishes, or chipping anywhere on this mug.