Although your question states the age that you were when you were charged with these crimes, it doesn't say how many years ago this was. Also, if you were charged as a juvenile in either of these, the juvenile record is NEVER revealed to adults (except law enforcement, who will be able to see "under" the seal of any record).
The new CORI law in Massachusetts states that a felony may be sealed after 10 years and a misdemeanor after 5 years by a mailed petition, but there are other considerations that can shorten that time. In your case, if each of your CWOFs has now been dismissed because the probation was completed successfully, you can wait out the time and mail in a petition, OR it is eligible for sealing by a judge. This involves submitting a petition and also a motion (an act that opens the case to put it back into court before a judge). The sealing requires that you show it is in the interest of "substantial justice", that you are able to show how sealing it serves a more important interest than the First Amendment interest of the public in knowing what you have done. As you can see, this is precisely what lawyers do best--advocate for the interests of their client. Therefore, while it is not technically required (you can always represent yourself in any court), your best opportunity for success in this process will be with the assistance of an attorney.
For links to the forms that are required, as well as more information on CORI, click the "CORI" blue link after this answer. Good luck.
Providing users with information is not intended to create an attorney/client relationship. However, if in reading my response, you are interested in retaining me to represent you, please do not hesitate to contact me.
For the malicious destruction charge, you were 16 at the time of the incident so it would have been charged as a juvenile delinquency charge. Delinquency charges are sealed via petition under G.L. Ch. 276, s. 100B and requires hat 3years have passed since the end of th probation, and that you have not been convicted of any crime in the 3 years preceding the request to seal. Your A&B dangerous weapon CWOF is not a conviction. If three or more years have passed since the end of your juvenile delinquency probation, you ar eligible to seal the delinquency matter.
As for the AB D/W charge, you could go about sealing that charge in possibly two ways. The first is if 10 years have passed since the start of probation have passed, and you have not been convicted any crimes in the 10 years preceding your request to seal, you can petition the Commissioner of Probation to seal under ch. 276 s. 100A. If less than 10 years passed, you are limited to petitioning a court to seal under ch. 276, s. 100C, which requires you to convince a judge that you case meets the tests for sealing, specifically that "substantial justice" requires sealing and that there is a "compelling governmental interest" which outweigh th public's interest to keep your record unsealed. Side note: Are you certain that the AB D/W charge was not amended down to a simple A&B? If it was amended down, this would make the charge a misdemeanor and shorten the waiting time to seal under 100A to 5 years.
An attorney is especially helpful in a 100C situation, and is also helpful in a 100A and 100B situation. There is a right way and multiple wrong ways to seal a criminal record. An experienced sealing attorney can get it done for you the right way.
Best of luck,
Disclaimer: This answer is provided for informational purposes only and it is not intended as legal advice. Additionally, this answer does not create an attorney-client relationship. If you wish to obtain legal advice specific to your case, please consult with a local attorney.
Both attorneys Peng and Leary have given you a great road map to follow in case you decide to do it alone. However, as it has been pointed out, it is not as simple as filing a paper; there are arguments needed to be made in order to maximize your chances of getting the desired outcome. Contact an attorney for a consultation in the matter, or contact your local bar association along with the Massachusetts Bar Association to get a referral for an affordable attorney in your area.
Best of Luck
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The above is NOT legal advice, and is NOT intended to be legal advice. No Attorney-Client relationship is created through the above answer.