Leap year
The name "leap year" probably comes from the fact that while a fixed date in the Gregorian calendar normally advances one day of the week from one year to the next, the day of the week in the 12 months following the leap day (from March 1 through February 28 of the following year) will advance two days due to the extra day (thus "leaping over" one of the days in the week). For example, Christmas Day (December 25) fell on a Sunday in 2016, and Monday in 2017, then it fell on Tuesday in 2018, and will fall on Wednesday in 2019 but then "leaps" over Thursday to fall on a Friday in 2020.
Hebrew calendar
The insertion of the leap month mentioned above is based on the requirement that Passover—the festival celebrating the Exodus from Egypt, which took place in the spring—always occurs in the [northern hemisphere's] spring season. Since the adoption of a fixed calendar, intercalations in the Hebrew calendar have been assigned to fixed points in a 19-year cycle. Prior to this, the intercalation was determined empirically: