Monroe and Jennings for Rondo looks like it could work for both. Monroe can't be traded until late December and he needs to consent to the deal because he loses his Bird rights if traded. However, with plenty of teams having cap space and him appearing to not want to stay in Detroit longterm, I think he'll consent.
I would want a pick if we're taking back Jennings' 2 year deal. Or we could include Wallace, while they include expiring contracts of Bynum and Jerebko, to facilitate a deal.
Makes sense for both teams. Monroe would give us a big man in the middle and allows us to take a closer look at him should we want to sign him longterm. Jennings would back up Smart, and provide that wildcard scoring off the bench like Crawford did.
Rondo clearly upgrades the Pistons PG spot. I question how a non-shooting trio of Rondo, Smith, and Drummond would work. However, the Pistons do have decent shooting surrounding them with Meeks, Caldwell-Pope, Butler, Augustin, and Datome.