Jesus and the Rich and Powerful

People sometimes like to say that Jesus hung out with the poor, not with the rich and powerful.   Well, the Gospels to seem say only that Jesus didn’t hang out exclusively
with such as them.  He clearly had friends, disciples, and would-be
followers who were at least somewhat well-off and/or influential.  For example:

• The Roman centurion whose servant Jesus healed (Mt.
  8:5-13);
• The royal official in Capernauam whose son was ill (Jn 4:46-54);
• Matthew’s tax-collector friends, who likely weren’t all impoverished (Mt. 9:10);
• Jairus, the leader of the synagogue, whose twelve-year-old daughter Jesus
  declared was not dead but sleeping (Mt. 9:18-25, Mk 5:22-23, 35-42);
• Joanna, the wife of Herod’s household manager, and other women who supported Jesus "out of their own means" (Luke 8:3);
• The rich
  young man (or ruler) who went away sad (Mt. 19:16-22, Lk 18:18-23);
• Jesus’
  friend Lazarus, whose sister Mary just happened to have costly perfume worth 300
  denarii, or about a year’s wages, that she used to anoint Jesus (Jn 12:2-5, NRSV
  footnote j).
• The owner of the house with a large guest room upstairs, furnished
  and ready for the Last Supper (Mk. 14:13-16);
• Nicodemus, a Pharisee who was a leader of the Jews (Jn 3:1);
• Joseph of Arimathea, the rich man
  and member of the council who claimed Jesus’ body (Mt. 27:57-58, Mk. 15:43).

In a related vein, the Gospels repeatedly tell us of the “great crowds” that
followed Jesus, from Galilee, the Decapolis, Jerusalem, Judea, and beyong the
Jordan (e.g., Mt. 4:25), as well as the thousands present at the miracle of the
loaves and the fishes. it seems a bit of a stretch to suppose that these crowds
were made up exclusively of poor people.

It also seems relevant that Jesus told lots of parables featuring rich and
powerful people. That in itself doesn’t prove anything about his social
connections. But it’s not implausible that he came up with these parables in
part because he had first-hand experience with such people.

Moreover, good
preachers and other communicators often tailor their messages to their particular audiences, the better to be understood by them.  Jesus may have sometimes told parables about rich and
powerful people precisely because that’s just whom he was talking to.