Checked the newspapers and this is what I found.

April 7, Monday. Whiteman and his team rehearse in Seattle before going on to give what is described as a preview showing at the Spanish Ballroom of the Olympic Hotel in Seattle
April 8, Tuesday. (6:00–7:00 p.m.) Whiteman’s Old Gold broadcast comes from the Civic Auditorium, Seattle, over station KOL and Bing is prominently featured with two solos, “It Happened in Monterey” and “Alice in Wonderland.” There is an audience of only 1500 in an auditorium that can seat 6000 and Whiteman curtails his concert somewhat. 

Songs from the latest talking screen successes will be played and sung during the coming Old Gold Hour tonight when Paul Whiteman directs his famous jazz orchestra from the civic auditorium at Seattle. The program will be relayed from that northwest city direct to New York, whence the Columbia System will transmit it over its nationwide network.
      Outstanding among the features of this hour will be Bing Crosby’s rendering of hits from two musical comedies now on Broadway. One is the waltz song, ‘It Happened in Monterey’ from Whiteman’s picture, ‘King of Jazz.’ The other is the novelty number, ‘Alice in Wonderland,’ from Harry Richman’s picture, ‘Puttin’ on the Ritz.’ With Crosby on the program will be the popular crooner, Mildred Bailey, who will sing ‘Blue Turning Gray over You’ and ‘I Still Remember.’ Jack Fulton, tenor, will sing the new ballad, ‘Romance,’ and Whiteman’s 32-piece band will include in its own repertoire such hits as ‘Why?’ from ‘Sons o’ Guns’ and ‘Hay Straw’ from ‘Song of the West.’ This program goes on the air this evening at 9 Eastern Standard Time.
(Press release)

Paul Whiteman and his symphonic jazz orchestra, who appear on the Old Gold offering via WABC, went “Sailing on a Sunbeam” and brought penetrating rays of music to our hearts—yes, they did. Bing Crosby warbled some pretty dittys, the most fetching of which was, “It Happened in Monterey” from the maestro’s picture, “The King of Jazz.” Jack Fulton sang about something that has always intrigued us, “Romance” and accomplished this to good effect. Mildred Bailey, blues crooner, said that she was “Blue Turning Gray over You”—wonder it she meant us. This was a good all around presentation.
(David Bratton, Brooklyn Times Union, April 9, 1930)
 
April 9–13, Wednesday–Sunday. Starting at 8:30 p.m. each day, Whiteman performs at the Civic Auditorium, Seattle. There is a matinee show and dance on April 12 and a grand concert at the Civic Auditorium on April 13.
April 14, Monday. Whiteman and his entourage arrive in Portland, Oregon, during the late afternoon by car and check into the Benson Hotel. They had been expected by train and a civic reception committee had been waiting at the railway station. (8:30–10:00 p.m.) Whiteman performs at the Auditorium, Portland, and the concert includes a “comic sketch by the Rhythm Boys.” The whole Whiteman ensemble then goes to Cole McElroy’s Spanish Ballroom where they play until 1:00 a.m.

Bringing his throne and dais, mace and sceptre with him, Paul Whiteman last night made Portland the capital of the mythical kingdom of Jazz. The jazz king appeared before some hundreds of his loyal subjects in the public auditorium for almost two hours earlier in the evening, dispensing some two-score of the musical items which have lent luster to Whiteman’s name. Later in the evening and on toward the dawn the throne and dais, and the famous band which accompany these impediments, held sway in Cole McElroy’s Spanish ballroom for the edification of those who would dance as they listen.
(The Oregonian, April 15, 1930)

Last edited by Malcolm Macfarlane (11/11/2025 9:02 am)

The Olympic Hotel in Seattle was built in 1924 and it incorporated a Spanish Ballroom. Can’t see that Cole McEnroy was involved in any way. Mildred Bailey was definitely on tour with the Rhythm Boys March 31, 1930-April 15, 1930. The Rhythm Boys left Whiteman after the show on April 15, 1930. Whiteman and his entourage then travelled to New York. Mildred appeared on the Old Gold Show with Whiteman on April 22, 1930, which was broadcast from New York. The Criterion Theatre in LA was showing King of Jazz on April 20. Cannot trace a Shrine Auditorium benefit on December 24, 1929.
The Whiteman troupe (including the Rhythm Boys and I assume Mildred) were at Loew’s State, Los Angeles from February 13–19, 1930. Cannot trace Bing being in Chicago in 1930 but he was there on several occasions both before and after 1930.
Hope this helps.
See also ‘Bing Crosby - Day by Day’ on www.bingmagazine.co.uk

Yes, the Nov. 14, 1929 and Dec. 12 1929 performances both show in my diary. Can't find much more about them though. Probably both the Rhythm Boys and Mildred would have taken part too. Can't help with Three Duces. Are you researching Mildred Bailey for any particular reason?
The Bing on Radio link on the BING magazine site has the content of all the Old Gold shows listed.

Bing and "The Three Deuces" club are mentioned in Eddie Condon's 1947 autobiography "We Called It Music" in a chapter labelled "The Three Deuces". Here's an excerpt which I've edited for clarity:
"After the show {Condon is referring to Paul Whiteman's appearance at the Chicago Theatre where they performed from Nov. 7 to Nov. 13, 1927-from there, they went to the Uptown and Tivoli theatres} I met Bix and took him to a speakeasy around the corner at 222 North State Street...About two o'clock we took our drinks downstairs and Bix played {likely piano}. Some of the other Whiteman boys followed us. Suddenly everybody was there and everybody was playing along with Bix. Some singers arrived but they kept quiet and listened. The were the Rhythm Boys-
Al Rinker, Harry Barris and Bing Crosby-sharp-looking lads, slightly young."
Condon goes on to mention that a second jam session took place the following night at the same location. While Bing is not mentioned, Condon does say that Bud Freeman, the Dorsey brothers and drummer Ben Pollack participated. The "Three Deuces" continued in business into the 1930s when great musicians like Art Tatum, 
Roy Eldridge and Zutty Singleton were part of the regular entertainment. I don't know of any other references to Bing and "The Three Deuces" but it's certainly possible that he returned there when he was in Chicago during the late '20s-early '30s. Mildfed Bailey may have also attended "The Three Deuces" when she was working with the Whiteman band at the Edgewater Beach Hotel in Chicago c. 1931.

Colin, Bing was on a cruise south along the Mexican coast on M.V. Kamika, deep-sea fishing with Lew Ayres, Nick Stuart, Lennie Hayton, and Eddie Lang from August 13-30, 1932. He then returned to LA. Meanwhile in Reading, Pennsylvania, the Embassy Theatre was showing a film called “Million Dollar Legs” supported by the Bing Crosby short “Hollywood on Parade” and Cab Calloway and His Orchestra. Whether this was a short featuring Calloway or a live performance I don’t know, Calloway was in Pennsylvania at that time though.

Nightclubs were the center of Capone’s business and, also, his source of relaxation. Kutner recalled that he went along with Capone time after time to hear Isham Jones at the College Inn, “a big hangout for the boys.” And he remembered when Bing Crosby, then an unknown from Spokane, Washington, was in town with Paul Whiteman’s Rhythm Boys, and showed up at the Three Deuces (a Capone cabaret). “He came into the Three Deuces with Bix Beiderbecke, who said that some dude had invited them to play in Cicero. They had been told that they would be picked up at the Deuces. . . . Crosby sat there biting his nails and drinking Coke. Chicago made him nervous, he said. . . . Finally one of Al’s limousines called for them. I went out with them and introduced myself to the driver: ‘You know me, I play piano for Mr. Brown (Capone’s pseudonym).’ Capone had set up the Greyhound Club for them to play in, with his boys patrolling the streets armed to the teeth like a small army. Bing stepped out of the door of the limousine, looked around at all the mugs toting submachine guns in the open, and asked me, ‘Is this a jazz joint or World War II?’ He had never before seen men carrying arms like this in the heart of an American city.”
(When Hollywood Had a King, page 22)

Last edited by Malcolm Macfarlane (21/11/2025 4:17 pm)

Malcolm
I am very familiar with your excellent research. I had thought that another California EMBASSY club would correspond with a Cab Calloway gig in the area. More so the Cab Calloway "Hi de Ho for AUGUST 29,1932" has a printed add noting both Bing & Cab Calloway. Under that it states, 'with Bing Crosby on stage" So that is incorrect. /
Al Capone's Chicago area clubs did include the "Three Duces". Other contemporary entertainers like Ethel Waters, Adelaide Hall, Fats Waller, Helen Morgan, Ruth Etting, & Louis Armstrong also found interest from Capone. In addition to the "Greyhound Inn'-later known as "Montmartre", there were "Colosimo's (still operating after "big Jim" being gunned down in the site in 1920),) the "Cafe de Paris"-bombed, "Cinderella Cafe", "Showboat", "Cocoanut Grove" and the "Cotton Club" in Cicero, Illinois-run by Al's brother, Ralph., and the Metropole Hotel There were others. . While as performers IN clubs, accounts note that they were PERSUADED to perform for Capone personally, in other locations-perhaps one of these noted above?