Issachar is the fifth son of Leah and the ninth child of Jacob.

^{Deuteronomy 33: 18} About Zebulun he said: “Rejoice, Zebulun, in your going out,
and you, Issachar, in your tents.
^{Genesis 49:14} “Issachar is a rawboned (strong) donkey lying down among the sheep pens. ¹⁵ When he sees how good is his resting place and how pleasant is his land,
he will bend his shoulder to the burden and submit to forced labor. (NIV)

Like most of the other sons Issachar does not have a lot documented about his life. We know that he was involved in looting Shechem, selling Joseph and the trips to Egypt but that is about it for the story of his life. His family is also pretty quiet but he does have a few standouts in his linage and they are mentioned when all the tribes come together or are being assigned things to do by David or Solomon. They are included in some of the revivals in the latter part of Chronicles.

Tola, a judge mentioned in Judges 10:1+2 is from Issachar and Deborah includes them in her song in Judges 5:15.

Baasha, a king of the Northern Tribes (Israel) is found in 1 Kings 15:27 – 16:7; the NIV mentions that the name may mean “bad” and he lived down to the meaning as he killed the previous king and his entire family. (That seemed to be standard practice for the day.)

Issachar with Zebulun and Judah formed the leading edge of the Camp during the Exodus; in fact those three appear together many times. I feel it is because they are the three “blessed” sons of Leah. Reuben, Simeon and Levi all incurred Jacob’s wrath during his lifetime. I also feel that they were the “true” children of a wife instead of a concubine. (Judah was not a poster child for good as he starts the selling of Joseph and had the trouble with his daughter-in-law.)

He and Zebulun are often mentioned together and were allotted land next to each other after the conquest. But like most of the Northern Tribes they go into Exile under the Assyrians and you loose track of them after that.

Another Issachar connection has to do with Gideon.  He was in Ophrah that was actually in the land of Issachar.  Several sources I have read refer to Manasseh mingling with both Issachar and Zebulun; a map in my Holman Bible puts much of his story in those lands.

Map from http://www.biblestudytools.com/resources/maps/twelve-tribes-of-israel-map.html and eBibleTeacher.com.