I had difficulty doing so, because it is unclear whether the former slave Shimon of Herod (who attempted to usurp the throne after Herod's death) was ever identified as a messianic figure (and was reportedly beheaded rather than crucified) whereas the Shimon Bar-Kokhba (who was identified as a messianic figure) occurs too late in history to fit the purposes of the OP (and the manner of his death is unknown, though old Jewish mystical tradition reports that he was miraculously saved). If you know of any evidence about a credible candidate for such a Shimon, tell us about it
The enterprise of distinguishing various "messiah" concepts in antiquity, based on modern cultural concepts, seems to me fraught with peril. It's natural to regard primitive Christianity as a sect within ancient Judaism, and under such a view the "Christian" notion of messiah may have had a "Jewish" counterpart at the time. In this context, it is interesting to note that Tractate Sukkah 52, for example, distinguishes "Messiah ben Joseph" and "Messiah ben David":
... Said Rab: They found another passage and lectured about it, <52a> namely <Zech. 12:12>: “And the land shall mourn, every family apart by itself, the family of the house of David apart, and their wives apart. And they said: Is this not an a fortiori conclusion? At the time of mourning, when the passions are so powerless, it is said the women and the men should be separate; so much more in the Temple, where they were occupied in rejoicing, and the passions can have power over them. What was the mourning for? R. Dosa and the rabbis differ. One holds that it was for the Messiah the son of Joseph, who was killed; and one holds that it was for the evil inclination, which was killed ... The rabbis taught: The Messiah ben David who (as we hope) will appear in the near future, the Holy One, blessed be He, will say to him: Ask something of Me and I will give it to you, as it is written <Psalm 2: 7>: “I will announce the decree. . . Ask it of Me, and I will give”, etc. But as the Messiah ben David will have seen that the Messiah ben Joseph was killed, he will say before the Lord: Lord of the Universe, I will ask nothing of You but life. And the Lord will answer: This was prophesied already for you by your father David <Psalm 21:5> ... http://www.hebrewroots.com/node/198As far as I can discover (as a googling amateur), this distinction between two messiahs in Jewish literature is not unambiguously known (in surviving documents) until around 200 CE, so it is difficult to known whether distinction is pre-Christian. If the distinction occurred in pre-Christian Jewish apocrypha, that could explain the interest of some early Christians in identifying Jesus of Nazareth as a descendent of David, born in Bethlehem, and of identifying the apparent father as Joseph, since such identifications re-combine the messiah defeated and the messiah triumphant; on the other hand, it also seems possible that the "two messiahs interpretation" could be an early Jewish reaction to Christian exegesis insisting on a messiah who was simultaneously a son of David and a son of Joseph; and of course, the "two messiahs" in Tractate Sukkah could also be neither precursor nor derivative of any Christian tradition