He's indecisive. He won't choose one side or the other. He wants it both ways.
SOURCE: Stutchkoff, Der Oytser fun der Yidisher Shprakh. Compare:
He's sitting on two chairs. | Er zitst af tsvey shtuln. | .ער זיצט אויף צוויי שטולן
SOURCE: Stutchkoff, Der Oytser fun der Yidisher Shprakh
Mit eyn hintn zitst men nit af tsvey ferd. | מיט אײן הינטן זיצט מען ניט אױף צװײ פֿערד.
You can't sit on two horses with one behind.
SOURCE: Kumove, Words Like Arrows