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By the security clearance regulations that Trump passed in 2017, he probably wouldn't get one.
https://www.debt.org/veterans/military-security-clearances/National Security Adjudicative Guidelines, last updated in July 2017, are clear about the link between security clearances and well-managed finances:
“Failure to live within one’s means, satisfy debts, and meet financial obligations may indicate poor self-control, lack of judgment, or unwillingness to abide by rules and regulations, all of which can raise questions about an individual’s reliability, trustworthiness and ability to protect classified or sensitive information,” the guidelines say.
...
Still, it’s financial irresponsibility — that is, an unwillingness to address debt trouble — that’s a bigger deal than actual bad credit. Context matters. Are your problems largely out of your control, such as a divorce, job loss, health emergency, or business failure? You may be in luck.
If, on the other hand, your financial troubles are an extension of personal foibles, such as gambling or alcohol addiction, or illegal activity, you can kiss that security clearance goodbye.
“Failure to live within one’s means, satisfy debts, and meet financial obligations may indicate poor self-control, lack of judgment, or unwillingness to abide by rules and regulations, all of which can raise questions about an individual’s reliability, trustworthiness and ability to protect classified or sensitive information,” the guidelines say.
...
Still, it’s financial irresponsibility — that is, an unwillingness to address debt trouble — that’s a bigger deal than actual bad credit. Context matters. Are your problems largely out of your control, such as a divorce, job loss, health emergency, or business failure? You may be in luck.
If, on the other hand, your financial troubles are an extension of personal foibles, such as gambling or alcohol addiction, or illegal activity, you can kiss that security clearance goodbye.