Extremely Negative
Yishmael was evil, and he committed the most heinous of crimes, including the threesome of idolatry, murder, and illicit relations.
SOURCES: R. Akiva and other Sages, Targum Pseudo-Jonathan, Pirkei DeRabbi Eliezer, Rashi
Prophecy to Hagar – "וְהוּא יִהְיֶה פֶרֶא אָדָם"
According to Resh Lakish in Bereshis Rabbah and Rashi, the angel's words pointed to the wickedness of Yishmael's character. Rashi asserts that he was to become a robber ("יָּדוֹ בַכֹל") who was to be hated and provoked by all ("וְיַד כֹל בוֹ"). Resh Lakish goes a step further, asserting that he would rob, not just possessions, but people's lives.
Avrohom's plea: "לוּ יִשְמָעֵאל יִחְיֶה לְפָנֶיך"
Rashi asserts that Avrohom was praying for the spiritual well being of Yishmael, that he should live a life that is "before God".
"מְצַחֵק"
These commentators suggest that the word refers either to idolatry, murder, or illicit relations, the three cardinal sins in Judaism.
Why did Sarah want Yishmael expelled?
Given such wicked behavior, it is not surprising that Sarah wanted Yishmael banished.
Why is Avrohom "upset about his son"?
According to Targum Pseudo-Jonathan, Avrohom was upset about his son's idolatry, not at the request to expel him.
Why did HaShem reject Yishmael?
Yishmael's actions proved him unworthy of a place in Avrohom's household and warranted his expulsion.
HaShem saves Yishmael
Targum Pseudo-Jonathan emphasizes that HaShem saved Yishmael only for the sake of Avrohom and his merits.
Yishmael after the expulsion
Most of these sources assert that Yishmael repented later in life. Pirkei DeRabbi Eliezer depicts Avrohom as checking up on his son, and leaving him messages to change certain behaviors, which Yishmael follows.
Why is Yishmael made into a great nation?
The Torah says that this was merely a fulfillment of HaShem's promise that Avrohom would be the father of a multitude of nations, rather than a reward for Yishmael's behavior. Some of these commentators even attempt to diminish this promise. Thus, R. Yitzchak in Bereshit Rabbah and Rashi assert that Yishmael's twelve princes will be short-lived ("כעננים יכלו"), and Targum Pseudo-Jonathan says that he is destined to become a "nation of robbers".
Yishmael's descendants
Rashi asserts that Yishmael's descendants plagued the Israelites later in history. As they were dying of thirst in route to exile in Babylonia, they begged their cousins for water but were refused.
Yishmael and Islam
Some suggest that only pre-Islamic Midrashim present Yishmael as worshiping idols, as that was the common practice of the Arabs of that period. Pirkei DeRabbi Eliezer, on the other hand, was written in the Islamic era, and thus even while painting a negative portrait of Yishmael, it nonetheless depicts him as monotheistic. Pirkei DeRabbi Eliezer also provides a postscript to the Yishmael story containing an account of Avrohom's subsequent visits to Yishmael. This account which closely parallels some Islamic traditions appears to also polemicize against them.
