Were all the Jews enslaved in Egypt?

Question

According to this Midrash there were Jews and

They had favored positions among the Egyptians and could not dream of giving up their wealth. Therefore, they died in the plague of darkness.

(Translation Here)

Do we have any background information about the fact that this midrash says that there were Jews in favored positions? Are we led to believe that there were Jews that were not enslaved? Or perhaps they developed these positions over the period of the 10 plagues? Or perhaps they weren't wealthy and the midrash is metaphorical and it means they lived "as if" they were wealthy, meaning they had gotten comfortable in Egypt and didn't desire to be redeemed?

Answer 1

Although Meir's response is more on the mark in answering your question based on the Midrash itself, another consideration is the Meshech Chochma (Vaera 8) who says

ויצום אל בני ישראל ואל פרעה כו' להוציא את בנ"י כו' יתכן כי גם אז במצרים היו גדולי האומה אשר היו שרים נכבדים ואפרתים והם היו משעבדים את בני ישראל לעבדים שמכרו המצרים להם ואולי היו המה השלשה שבטים ראובן ושמעון ולוי שהנהיגו שררה במצרים כמו שאיתא במדרש נשא פ' י"ג לוי שלא היה בשעבוד מצרים לכן לא נטל נחלה בארץ, וכן ראובן לא נטל רק בעבר הירדן ושמעון נתקיים עליו אחלקם ביעקב כמוש"פ רמב"ן ומהם היו בני חורין הרבה ושרים אשר היו משעבדים את ישראל הנמכרים להם מהממשלה של פרעה, לכן צוה השי"ת שבני ישראל גם פרעה יוציאו את בני ישראל מהשעבוד

Essentially, the commandment told "to Klal Yisroel and Pharaoh to remove the Jews from slavery," refers not only to the Egyptian leader's requirement to send us out, but also to the tribes in power who had Jewish slaves. Specifically, Reuven, Shimon, and Levi who did not receive an inheritance in Eretz Yisroel proper had more independence in Egypt to have Jewish slaves (perhaps not having the land to hope for would have made being a slave too emotionally crushing). Although the Meshech Chochma does not suggest the Egyptians desired their position of power, it does note the higher positions these tribes had.

Answer 2

The actual expression in the Midrash there is

שֶׁהָיוּ פּוֹשְׁעִים בְּיִשְׂרָאֵל שֶׁהָיָה לָהֶן פַּטְרוֹנִין מִן הַמִּצְרִיִּים וְהָיָה לָהֶן שָׁם עשֶׁר וְכָבוֹד

there were wicked Jews who had Egyptian patrons and who had wealth and honor.

In other words, these Jews were indeed slaves or dependents of these Egyptian masters/patrons, but through their association with said masters, they could amass fortunes of their own. Compare https://en.wikipedia.org/wiki/Slavery#Dependents:

"Slavery" has also been used to refer to a legal state of dependency to somebody else. For example, in Persia, the situations and lives of such slaves could be better than those of common citizens."

So it may well have been the same in Egypt.