Looks like you have a double leader there. If you are considering removing it, you may want to do it in stages where you cut the left side back part way to back to a lateral branch and then allow the right side to fill out and become dominant. Once the dominant side has spread out more in the crown, you could take the left limb off at the trunk. I am not an arborist but would consider getting a certified arborist's advice since you are correct - that IS half the tree. It relies on those leaves to produce energy, so staging it may be of value so it suffers less shock.

Also, get some mulch down to help reduce bark damage from mowers and trimmers, but not directly against the bark.

i would start .. by removing the grass in a 3 foot circle around the base ... and adding some good course mulch ....

i would then take the hand shears.. and remove everything at least 2 feet above the large branches where they 'Y' .. so i could really see what is there ... if the branch is too big for a good pair of hand shears .. i would leave it for now ... to saw it later.. once we come up with a plan ...

after that.. i would stick my head in there.. and remove any damaged or crossing branches ... that are being damaged.. remove at least one ...

then i would snap another pic.. post it here.. and ask where to go from there ...

second pic.. there is a white dot in the middle of the tree ... whatever is back near the fence.. my tree would be bare of everything but the major branches.. to at least that height ...

we dont do live oak up here in MI ... so if timing of when to do it is important.. i would leave it to others with that knowledge ... [in fact.. up here.. the trees lose their leaves ... and that is the best time to 'look' at what is there to 'see' the structure' ... i suppose your is evergreen and there is no need do wait???]

in my world.. if that tree were bare to 8 or 10 feet .. in the future .. that would be the 'goal', presuming you dont live on a golf course and have space for a ground hugging tree ..

as it stands right now ... it has the potential to be a bush.. rather than a tree ... and that is why you are getting ready for the job ... eh

lets see what the other say ...

do you have a GOOD pruning saw ... you should have a knockoff version of the one at the link.. no more than 15 bucks at the bigboxstore ... though i havent bought one in a few years.. so who knows how much they are now ... though you should not have to mail order ... the key is two rows of surgical razor sharp teeth ... will cut that tree like butter ... this is a case where the right tool matters.. IMHO ....

ken

Here is a link that might be useful: link

I removed a few branches, and it definitely is starting to look more like a tree, thanks for the help too. I think that side branch on the left has a couple issues, first being it's still half my tree, and you can see another branch on that branch that is super close together. Look at these pics and see what you think, going to get mulch this weekend.

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pic above... the intersection of two major limbs is called a crotch .. [you cant really make this stuff up ...]

the one on the left.. is future failure .... it will collapse.. probably the day after you are extremely satisfied with your 50 year old tree ... or in the next severe wind storm

i dont know what to tell you about how to prune it .. and will await .. with baited breath [again.. what the heck does that mean] .. as to how to fix it ...

the other one doesnt look much better ...

man.. you didnt waste any time cuttin that chucker up.. lol ...

when this tree is 50 years old.. and 75 feet tall .... that trunk will be straight as an arrow .. and it wont matter if half the canopy has to go now ... forget about worrying about your 'half the tree'.. your concerns about what needs be done.. is very short sited .... put in your mind .. what the 20 year goal is.. and dont worry about what proper pruning will do to it in the first few years here and now ...

but removing 3 of them.. and training a single trunk.. is going to be a 3 or 4 year program/project .... not something you are going to do in the next week ....

i need more opinions ... please include a discussion of crotches and included bark ... never forget.. you can always take more next year.. you cant staple or glue them back on ... [where are dan and Brandon???]

ken

Thanks Ken, you are definitely right about being short sited, this is actually a short period of the trees life, if you think of it in terms of a tree. My only concern is that I don't shock the tree or anything. I will wait for other responses before I make my next move. Next move I'm thinking will be to remove the left inside branch and the let the tree fill in the void some. Then eventually remove the whole left branch, then work on the right side over the next few years. That's my plan so far, ofcourse it may change because I'm no expert. Thanks again for all the help.

"man.. you didnt waste any time cuttin that chucker up"

ROFL. That's funny.

"training (to) a single trunk.. is going to be a 3 or 4 year program/project"

Definitely. If that's the way you decide to go, do it slowly as advised above (mustard_seeds, et al). I think you've removed enough for this go-'round.

The next step I would take is to elliminate the turf/weeds from a 3'+ radius circle around the trunk and mulch correctly.