Pawn and Two: <Chicago Chess Man> 17...O-O-O is certainly more risky than 17.O-O. Bogoljubov may have expected 17.O-O-O would give him more counter chances.In their book, "World's Championship Match", F.D. Yates and W. Winter stated in regard to 17...O-O-O: <"Too venturesome, 17...O-O, left a good and playable game".>
Alekhine in his notes for this game, stated in regard to 17...O-O-O: <"In making this risky move Bogoljubov already planned the sacrifice at e5 which, doubtless, gave him some fighting chances. He can hardly be blamed for that decision, inasmuch as the alternative 17...O-O 18.Nd5 Bxd5 19.Qxd5 Rfd8 20.O-O-O Nf8 21. Qb7, etc., would have left him but very few chances of salvation.">
As there is some difference of opinion regarding the merits of 17.O-O or 17...O-O-O, it is helpful to get Fritz 9's evaluation.
Fritz 9 prefers 17...O-O and gives the following evaluation and line of play:
Evaluation after 17...O-O: (.63) (18 ply).
17...O-O 18.Nd5 Bxd5 19.Qxd5 Rad8 20.O-O Nb8 21.Qb3 Qxe4 22.Nc3 Qa8 23.f5.
After 17...O-O-O, Fritz 9's evaluation and line of play is:
Evaluation after 17...O-O-O: (1.18) (16 ply).
17...O-O-O 18.Nd5 Qd6 19.Qa4 Bxd5 20.Rd1.
Based on Fritz's evaluation and suggested lines, it does appear that 17.O-O may be a better move, but White would still have an advantage.
However, Bogojubov and Alekhine may be correct that 17...O-O-O may provide more counter chances.
Look what happened next! At move 18, Alekhine, instead of playing the strongest line indicated by Fritz 9, 18.Nd5, played 18.Qa4.
After 18.Qa4, Fritz 9 provides an evaluation of (.62) (16 ply). Fritz indicates the following line: 18...f5 19.O-O Kb8 20.Bc6 fxe4 21.Nxe4 Bxb2.
At move 19, Alekhine again played differently from Fritz with 19.e5.
Bogoljubov was now getting the fighting chances that he was hoping for after playing 17...O-O-O. Next followed some real fireworks with both Bogoljubov and Alekhine sacrificing material. Bogoljubov sacrificed a Knight at move 20 and Alekhine sacrificed a Pawn at move 24.
At move 28, the game was decided when Bogoljubov blundered with 28...Kb8??. Alekhine's reply 29.Ned4! was immediately decisive.
Alekhine stated: <"A longer resistance was possible after 28...Nxf2 29.Kxf2 Kb8; but by continuing 30 Ng3 Rhf8 31.Ra3 (followed by 32,Re3 or Rd3, etc.)-White would still increase his pressure in a decisive manner".>
In Yates's and Winter's book of the match, they make no mention of Bogoljubov's mistake, 28.Kb8??.
In 1954, in "Kings of Chess", Winter stated that after 28...Nxf2 29.Kxf2 Kb8, White would still have the advantage, but the disappearance of the Bishop makes the win much more difficult.
Fritz 9 clearly showed that after 28...Nxf2, Alekhine's suggested line would lead to a certain draw.
28...Nxf2! 29.Kxf2 Kb8 30.Ng3 Rhe8 31.Kg1 Rd5 32.Rc4 Qe3+ 33.Kh1 f4 34.Re4 Re8xe4 35.Nxe4 f3 36.gxf3 Qxf3+ 37.Kg1 Qe3+ (.00).
A small advantage for White, per Fritz 9, is still possible after 28...Nxf2: 29.Kxf2 Kb8 (.30) (18 ply) 30.Ra3 Qd7 31.Rab3 Qd2.
Or 28... 29.Kxf2 Kb8 30.Rd1 (.32) (18 ply) Qc6 31.Rxd8+ Rxd8.
Any win for White after 28...Nxf2 would be very difficult to prove. The line Alekhine gave appears to be a draw.
In summary, I think Bogoljubov was right in chosing 17.O-O-O. It may not have been the best move according to computer programs, but based on his style and abilities, it was probably his best chance to obtain counter chances.
Unfortunately, Bogoljubov missed a very good chance for the draw, had he not overlooked the more obvious 28...Nxf2 and Alekhine's winning move 29.Ned4.