Mitch,
Thank goodness, the TI survived.
This afternoon I decided I need to understand what the heck happened.
Here is my CSI analysis of the situation.
There is the electric gate, and the tree on the right. As I passed through the gate (I think I might have hit the button for the gate to close). Which it did, and it caught the left side of the trailer and then pushed the trailer into that tree. I did not realize this was happening (still - user error - isnt it?). Anyway the rest is history. The important part is coming up.
Gate, Tree and note the grass to the left of the tree.

Right side of rear brace caught this part of the tree. Ah - so left side pinned by gate, right side pinned by tree. This is not going well is it? Now I see why the rear brace snapped in two. It gets a little better.

Now, I am thinking if this is where the trailer got caught - I wonder where the kayak rudder hit? I could not tell exactly but after an hour or so - I found the top portion of the rudder pin. Nice. It was a nice jagged break and fit great with its other piece. Anyway, now that I found this piece I reasoned that the missing part of the rudder must be (hopefully) somewhere near where I found the rudder pin.
I found the rudder pin kind of the upper middle left of the picture. And started my search for a little piece of black plastic.

Another hour goes by - looked all over the place - and Ta DA! Found that dern thing!
Look right in the middle of the pic - there it is, hiding in the grass! Awesome!

So - I have these little parts. Can I glue them - heck lets try!!!

I go to Hobby Lobby and get some glue called Extreme Power - It is Cyanoacrylate ester. Seems good to me - suppose to be strong.
And some bought some accelerator - which speeds up the bonding process.
I glued the pin and then the rudder assembly. Waited a few minutes and put it back together.
Works! Steers fine, ruder up/down work. It seems pretty strong. I will still get another pin and rudder assembly but maybe it will work?


After all that - we put the sail up and took a snap.
2nd day was better than the first!

Thanks for all the support and comments.
Hope to make it to the water soon...