Since we are having fun “re-doing” the draft, I’m going to take a different direction. Following your premise that Trubisky is available at 3, I would then trade down to 12 for a very fair TVC deal which would be appealing to the Browns. Browns get 3 (2200), Bears get 12, 33, 52, 145 (2193). There is now no reason to trade down to 45 to recoup additional picks.
12 Deshaun Watson QB
33 David Njoku TE (the fudgies don’t trade back to 33 now and instead just select King at 29)
36 Markus Williams FS
52 Chidobe Awuzie CB
67 Jordan Willis OLB or Chris Wormley DE
111 Josh Malone WR (no need to take Jackson here, Josh is a 4.4 guy who caught 11 TDs from Dobbs in 2016 )
117 Tarik Cohen RB
fill in the rest for 145, 147, 221