As a missionary working in Israel in the 80's, I spoke to many Jews about why I believed that Jesus was the Jewish messiah. One of the platform declarations I would make is that there were some 300 prophecies from the Jewish Scriptures which were fulfilled in Jesus' alleged virgin birth, his ministry, his death on the cross/tree, his three day burial*, his resurrection, and his ascension. I would cite many of the connected "fulfillments" between the testaments to show inquisitive Jews how these prophecies were validated.
In truth, I was unwittingly shooting an arrow, drawing a bulls-eye, and then claiming pinpoint accuracy as an archer!
About a year and a half ago, I wrote an article on this subject which was published on Jewsweek.com. You can read that here.
* No matter how you calculate it, there is no way that Jesus spent three days and three nights in the grave as he said he would. All the gospel accounts are fuzzy on this point. This is disturbing because of all the specific events Jesus said he would fulfill, being in the grave for three days and three nights was "the sign" that would be given to validate his claims. Mt. 12:38-40 says: Then certain of the scribes and of the Pharisees answered, saying, Master, we would see a sign from thee. But he answered and said unto them, An evil and adulterous generation seeketh after a sign; and there shall no sign be given to it, but the sign of the prophet Jonas: For as Jonas was three days and three nights in the whale's belly; so shall the Son of man be three days and three nights in the heart of the earth.
The most ancient of Christian traditions tell us that Jesus supposedly died on the afternoon of Good Friday and rose before dawn on Sunday. There is no way one can derive three days and three nights from this account. There are many discussions on this serious problem. I've never read one that adequately resolves this contradiction.
Furthermore, Jesus made the claim about the three day/three night sign to "certain of the scribes and Pharisees". It would make sense by every stretch of reasonability that Jesus would return to this "certain" group following his alleged rising from the dead in order to deliver the sign. However, according to the gospel accounts, he did not. He appeared only to those predisposed to believe in him. So, how is this a sign if only a select few are entitled to see it?
When G-d delivered the Torah to the nation of Israel at Mt. Sinai, the event was witnessed by millions.