If there is a trade to be made with Detroit it revolves around Monroe and Rondo.
Thing is, what's Detroit gonna do with Brandon Jennings if they make a trade for Rondo? Is anybody gonna take on that contract?
Jennings' contract isn't all that bad just 2 years left 16.3 million total. Still just 24 and not a horrible player (his 2PT% is bad, but he is a respectable 3PT and FT shooter).
I would guess during free agency, a reasonable trade for Detroit and Boston would be something like this.
Monroe (S&T 4 yrs, 60 million), Jennings (2 yrs, 16.3 million), Singler (1 yr, 1 million), Caldwell-Pope (1 yr 2.77 million with 2 more years of team options), Jerekbo (1 yr, 4.5 million) (total ~ 31 million)
for
Rondo (1 yr, 13 million), Bradley (S&T 4 yrs, 25 million), Bass (1 yr, 6.95 million), Anthony (1 yr, 3.8 million) (total ~ 30 million)
That trade seems to be fairly reasonable for both team. Boston gets a lot younger and Detroit gets a much better fit for its roster. Other players and picks of course can be added, but I do think that is a pretty solid trade on the hole (depending on just how much you value Monroe of course).