I think it will be 2019 until you can really compare Watson and Trubisky. The difference in experience and NFL readiness is too vast right now.
That is fine, but for my little experiment I looked though the play by play of Watson 3rd down passes vs Cleveland
First Drive
Q1 14:04 3&1 Deshaun Watson right end for 8 yards (tackle by Joe Schobert)
Q1 11:05 3&6 Deshaun Watson pass incomplete short left intended for Will Fuller (defended by Jamar Taylor)
2nd Drive
Q1 5:05 3&11 Deshaun Watson pass incomplete short middle intended for Ryan Griffin
3rd Drive
NO 3rd down throws. Watson did hit a wide open Will Fuller on a busted play for a 39yard TD
4th Drive
Q2 8:32 3&9 Deshaun Watson middle for 3 yards (tackle by Joe Schobert and Myles Garrett). Penalty on Chris Clark: Offensive Holding (Declined)
5th Drive
No 3rd down passes
6th Drive
Q2 1:54 3&10 Deshaun Watson sacked by Myles Garrett for -8 yards
7th Drive
Q3 10:17 3&1 Deshaun Watson pass complete short middle to Braxton Miller for -6 yards (tackle by Derrick Kindred)
8th Drive
Q3 3 and 5 Deshaun Watson pass incomplete deep right intended for Will Fuller.
9th Drive
No 3rd down passes - Watson intercepted pix 6 on a deep throw to Fuller on a 2nd down pass
10th drive
Q4 12:43 3&13 Deshaun Watson middle for 9 yards (tackle by Christian Kirksey)
This was his last pass. Houston ran the ball the rest of the game to chew the clock.
Summary Watson went 1 for 9 on 3rd down passes only hitting the 3&1 pass on the very first set.
On 3rd & 6 or more the money down he was 0 for 5.
Watson looked good for the most part. playing with a lead throughout the entire game with little pressure, but he did not preform well on the obvious passing downs.
I will update this when Trubisky plays this same defense.