Most likely yes, but accompanied by the right parent, i.e. the one who did not previously overstay.
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Yes, he will be able to re-renter the USA in the future, but most likely not with overstaying parent, unless the overstaying parent's US visa status should change.
Overstays do not count for individuals under 18. There are re-entry bars for those older. Contact a US immigration attorney for assistance and a family attorney if there are custody issues.
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