It depends is a team wants him in a toss in. Say to get a LF a team would take Jackson and Olt. I believe Olt will become a quality major league player. His 3B D is really good. With his power all he has to do is hit .260 or higher and he becomes a quality 3B in the league. If it wasn't for Bryant I would have rather have kept Olt out there to adjust like they are doing with Baez.
Now on a team with a need? Yanks could move A-Rod back to SS. Gardner would be a good return and nets a legit lead off. Jackson's value sours that deal but I believe that Jackson was just jinxed as a Cub. He is not that bad.
I think A-Rod has seen his last days at SS even if he comes back. If the Cubs could swing a deal with Castro or Baez headlining the deal and Michael Pineda headlining it the other way, I think that would be a fair proposal for starters (may need a sweetener either way) since both teams need players like that.
The Yankees could get young at SS again, and the Cubs could get a TOR pitcher who is just 25. Plus, the Yankees have the funds to easily replace Pineda with a Scherzer, Lester, and/or Santana.
Keep Castro or Javy at SS for now till Russell joins, and the Cubs could thrust their money at Cabrera and Shields to strengthen the team and still have a very modest payroll with a very formidable rotation.