In light of the Gaine firing, I think that this question is a really interesting one now.
Obviously the boss thought that Gaine failed at the draft. This is what I would've done.
1st round - trade with RAVENS for #22 - (Ravens get #23 and #86)
#22 - select - Andre Dillard - LT (best pass-blocking LT in draft)
2nd round
#54 - select - David Long - CB (top 3 cover-corner in draft IMO)
#55 - trade with CHIEFS for #61 & #167
#61 - trade with RAMS for #94 & #99
3rd round
#94 - trade with Bengals for #110 & #183
#99 - trade with Colts for #129 & #135
4th round
#110 - trade with Falcons for #117 & #186
#117 - select - Hjalte Froholdt - C/G (future starter at C or G)
#129 - select - Foster Moreau - TE (best blocking TE in draft, athletic potential to become weapon receiving as well)
#135 - select - Justin Hollins - OLB (Just needs a bit more bulk before he can start, athletic freak)
5th round
#161 - select - Charles Omenihu - DE (Perfect body for 3-4 DE, better pass-rush than people give him credit for)
#167 - select - Trayveon Williams - RB (He can run and catch, instant upgrade over Foreman
6th round
#183 - select - Drew Forbes - RT/G (Good feet, might be best at guard)
#186 - select - Olisaemeka Udoh - RT (Prototype project OT, big, long, athletic, just needs to be taught the game)
#195 - select - Kelvin Harmon - WR (Best hands in the draft)
7th round
#220 - select - Jordan Brown - CB (Has all the tools to be a starter, just needs to reach his potential)
ALL trades were deals that happened in the real 2019 draft. but with teams that drafted after us, so we easily could've made all of these deals.
#55 deal was #56 in real draft
#61 deal was #70 in real draft
#94 deal was #104 in real draft
#99 deal was #109 in real draft
#110 deal was #111 in real draft
and the trade up for Dillard was a known option
We had a lot of needs going into this draft since Free Agency was mainly a bust...so trading for more picks was needed. The good teams aren't afraid to trade up and down.
UDFA priority targets -
Porter Gustin - OLB
Andrew Beck - TE
Kyle Phillips - DE
Darius West - S
Ross Reynolds - OG
Mark Fields - CB
Jazz Ferguson - WR
Ashton Dulin - WR
Alex Barnes - RB
Dominick Bragalone - FB
Yosuah Nijman - LT - maybe the best athlete per size, but really bad technique at the moment
I'd sign up as many extra O-linemen with good athleticism as possible, someone is gonna hit, not sure why we didn't bring in more UDFA lineman
DJ Coker - OL
Brian Fineanganofo - RT
Ryan Crozier - OL
Mitch Hyatt - LT
Brandon Hitner - RT
Ryan Bates - OG
Calvin Anderson - OL