ESV - 16 Therefore let no one pass judgment on you in questions of food and drink, or with regard to a festival or a new moon or a Sabbath.
I want to offer an explanation that I don't hear too often in churches. Let me quote the verse in question: “Therefore let no one pass judgment on you in questions of food and drink, or with regard to a festival or a new moon or a Sabbath. These are a shadow of the things to come, but the substance belongs to Christ.” (Col. 2:16, 17) Why do we have to translate the verse as if Paul were telling these Messianic Gentiles, “Don't let anyone (presumably Messianic Jews) judge you for NOT keeping kosher, feasts and Sabbaths just like they do. Those things are just shadows. You have the substance which is Christ…”? This interpretation does not fit with historic accounts of who was judging whom, and why. If we back up into the chapter, we can gain a better context in which to work from. We know from Col. 2:6-15 that Paul is admonishing his readers about the wonderful forensic realities that they now possess in Messiah. They have truly been grafted into Isra'el (Rom. 11), they have been brought near to God and to the Commonwealth of Isra'el as fellow heirs and fellow citizens (Eph. 2), and they have received the more important circumcision—that of the heart (Col. 2:11). It is in this context that Paul comforts his readers with the famous passage in Col. 2:16, 17. He tells them not to let anyone (outsiders, pagans, Jews and Gentiles outside of Messiah, etc.) judge you for who you really are and what you do in Yeshua (Jesus). You are the righteousness of God in Messiah! (read 2 Cor. 5:21) Hallelujah! Why would Gentile outsiders be judging Paul’s readers? History shows that pagans and Gentiles outside of Messiah would often judge Gentile Christians for no longer attending the state required emperor celebrations with all their vile lewdness, demon worship, blood rituals, nudity, sexual promiscuity, and all-purpose pagan pageantry. That this judgment would eventually fall upon them is a given and Paul challenges them to hold their ground and not return to the former life of debauchery that they have been graciously rescued from. However, Scripture likewise attests that Gentiles attracted to Isra'el’s God and Isra'el’s laws would attend the synagogue alongside Jews (read the numerous accounts in the book of Acts). After coming to faith in the Jewish Messiah, it was natural for these Messianic Gentile believers to begin walking out the Torah just like their Messianic Jewish brothers were doing. However, the unbelieving Jewish leaders would always become jealous and outraged that Paul was teaching these Messianic Gentiles about their equality to Jews in Messiah. Remember, the Judaisms of Paul’s day practiced a social class/caste system in which Gentiles were not worthy to be counted as genuine covenant members in Isra'el without going through a ceremony of the proselyte. Thus, in this imbalanced view of covenant membership, the Torah was seen as a Jewish-only document. In their eyes, the Gentiles had no right to keep the feasts of the Jews—even if they believed in the Jewish Messiah (recall in Acts 15:5 that even some believing Pharisees wanted these Gentile Christians to becomes Jews before they could be received in the community). Paul came to set the record straight: in Yeshua, the Messianic Gentiles have every right to keep kosher and keep the Feasts just like Messianic Jews, since both constitute the Remnant of Isra'el. So, the verse should be interpreted as Paul telling these Messianic Gentiles, “Don't worry if the unbelieving religious Jews judge you for KEEPING kosher, Feasts, New Moons, and Sabbath observances—without becoming legally recognized Jews first. You are grafted into Isra'el—as Gentiles—via your faith in the King of Isra'el. In the end, you will most likely get kicked out of their synagogues and out of their festive celebrations because you did not change your ethnicity, but don't worry, those things are a shadow nonetheless. You have the SUBSTANCE that those shadows point to—which is Messiah himself.”