My guess at 53-man roster:
QB (2)- Trubisky, Daniel.
No-brainer. Bray had a shot, and granted it's been w/ guys that aren't making the team, but he's been trash in games. A lot of Bears fans hate Daniel, but he's exactly what a backup QB is. A dude that knows the offense and can help by communicating well w/ the starter. But also a dude that you never want to actually play. If he does have to play, see last year. Short passes, gimmick plays, letting Cohen throw the ball. No reason to care about the #2 QB.
RB (4)- Cohen, Montgomery, Davis, Whyte Jr.
Top 3 set in stone. The 4th comes down to draft pick, Whyte vs. a UDFA, Nall. Whyte has uncoachable speed, and Nall can likely be kept on the practice squad. Outside chance of all 5 kept. Bears kept Howard, Cohen, Cunningham, Mizzell (as a RB), and Mike Burton (as a FB) last year.
WR (6)- Robinson, Miller, Gabriel, Patterson, Wims, Ridley
Marvin Hall has a shot to make the team, but he's not much of a route runner and didn't look like a good option to return kicks as a backup either. I honestly would dangle Wims as a potential trade target. If the Bears can get a potential guy for the pass rush rotation for their 5th WR, I'd gladly make that trade.
TE (4)- Burton, Shaheen, Braunecker, Sowell
Bears have some potential sleepers here in Ian Bunting, Dax Raymond, and Jesper Horstead, but all project as better receivers than blockers now and in the future. Sowell makes the team as he's the only of the 4 that can block adequately. 2 of the 3 above probably go to the practice squad.
OL (9)- Leno, Whitehair, Daniels, Long, Massie, Larsen, Coward, Bars, Clemmings
Starting 5 pretty well set. Larsen has the ability to back up OG or C so he's the 6th. Bars has been strong thru 2 preseason games, and is too talented to try to pass thru waivers. Kept a 2nd backup tackle because IDK Coward's status w/ the elbow injury. But if he can go, the 9th lineman would be a prime cut candidate when you need someone at another position. Would also watch for a released player as a swing tackle. Coward didn't look great week 1 of preseason.
DL (5)- Hicks, Goldman, Robertson-Harris, Nichols, Bullard
Top 4 are a great group, set in stone. Bullard probably stays as he does provide a decent rep or two per game inside, though not the best fit. I know they like Nick Williams too, but I elected to keep an extra DB over him for special teams reasons. If they could find a taker for Bullard for a 7th or for another player at the end of their roster, I think they'd do it.
OLB (4)- Mack, Floyd, Lynch, Irving
Not a deep position. Don't like the 4th and the 3rd has had health issues in the past. Good thing the best edge in the league is here. James Vaughters has looked good in the preseason, but more of a practice squad to me at this point. Fitts looks mostly talentless and shouldn't make the team just because he was drafted late last year.
ILB (5)- Trevathan, Smith, Igeyibuniwe, Woods, Pierre-Louis
Kwiatkoski is a FA after this year, and got a raise to 2Mil this year due to arbitrator ruling. He's not worth the money, as he can't be put on the defense. Can't cover at all. Woods is a former safety w/ athletic upside. Pierre-Louis is a better special teamer who's cheaper than Nick Kwit.
CB (6)- Fuller, Amukamara, Skrine, Shelley, Toliver, Franklin III
The Bears actually have some interesting guys competing for that 6th CB spot. Franklin, Joseph and Duck. The competition's losers are both practice squad possibilities. Franklin gets the edge for me because of his speed and probably projects as the best special teamer of the 3. Not sure how much Denmark has practiced, but looks like potential IR stash. Definitely shouldn't make the roster just because he was drafted.
S (5)- Jackson, Clinton-Dix, Bush, McManis, Houston-Carson
McManis and DHC both make it here for special teams. McManis has the versatility to play nickel, so he stays. DHC could be the odd man out if they elect to go with an extra player at another position. 4 of 5 are FAs after this year, so no long-term help here and nothing really worthy of a practice squad spot.
ST- Pineiro, O'Donnell, Scales
Obviously just cut Fry yesterday. I liked Pineiro better anyway. Accuracy seems to be similar, go with the bigger leg. Maybe bring in another guy here, but I think they might as well develop what they already have instead of someone else's cast off.