Caveat: I do not use Cassandra. But perhaps this will help.
Data types
As you seem to have learned, do not store date-time values as text when your database supports an appropriate date-time data type.
Text formats
And, FYI, your format for representing a date-time value is terrible. When serializing date-time values as text, use the standard ISO 8601 formats.
Moment versus date-with-time-of-day
Another problem: You are trying to track moments with your use of type timestamp in Cassandra, but your stored strings such as Wed Jan 15 14:29:00 2020 is not a moment. Without the context of a time zone or offset-from-UTC, we cannot know if that time of almost 2:30 PM is 2:30 PM in Tokyo Japan or 2:30 PM in Toledo Ohio US, two very different moments several hours apart.
If you know the intended time zone for that date and time-of-day, apply a ZoneId to get a ZonedDateTime. I will assume that UTC (an offset of zero hours-minutes-seconds) was intended.
OffsetDateTime odt = ldt.atOffset( ZoneOffset.UTC ) ;
See this code run live at IdeOne.com.
Database
If you have a driver for Cassandra that supports JDBC 4.2 and later, you should be able to submit this java.time object directly.
myPreparedStatement.setObject( … , odt ) ;
If not, you can get a count of milliseconds since the epoch reference of first moment of 1970 UTC.
long milliseconds = odt.toInstant().toEpochMilli() ;
milliseconds: 1579098540000
Going the other direction.
Instant instant = Instant.ofEpochMilli( milliseconds ) ;
getting this error: DateOverFlowWarning: Some timestamps are larger than Python datetime can represent
I can only guess. Somewhere in your toolchain is a Python library. I suppose that library is limited to using a 32-bit integer. But you need a 64-bit integer to represent the count of milliseconds since 1970-01-01T00:00Z for a Cassandra timestamp value.
About java.time
The java.time framework is built into Java 8 and later. These classes supplant the troublesome old legacy date-time classes such as java.util.Date, Calendar, & SimpleDateFormat.
To learn more, see the Oracle Tutorial. And search Stack Overflow for many examples and explanations. Specification is JSR 310.
The Joda-Time project, now in maintenance mode, advises migration to the java.time classes.
You may exchange java.time objects directly with your database. Use a JDBC driver compliant with JDBC 4.2 or later. No need for strings, no need for java.sql.* classes.
Where to obtain the java.time classes?
