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School A offered 135k and school B offered 105k.

I really want to go to school B so I showed them School A's offer and they matched 135k.

I asked for an increase at school A and they gave me 150k.

Would school B be less inclined to match 150k from school A now since I showed them a lower offer from school A? They are both peers in the T14 but I'd rather go to school B even with less money.

How successful are second round negotiations after receiving an increase initially? Are schools usually out of money by this time of the cycle?

UPDATE:

They wouldn't match the offer the second time?

Even though they didnt match, Im still going to Cornell, but how should I go about getting a little extra $?

Should I ask again after the deposit deadline? If so, what would I say?

Georgetown & Cornell ? If so, then $15,000 shouldn't deter you from attending one over the other because they offer such different environments.

Whether or not the other law school will match probably depends in large part upon that school's yield of scholarship students. You won't know for sure unless you ask. Also, how you ask is important.

It wouldn't deter me at all, but 15k is a lot of $$$.

I'm just worried about the idea of showing them an new offer from a school they already matched

Then it comes down to how you present it to the other admissions office. One approach to consider, if true, would be to state that if you match the other school's offer I'll attend. Another approach could take a humble tone: $15,000 is a lot of money to me, are you able to offer any more scholarship money ?

update in the bold in the OP

In my opinion, Cornell is worth the extra money. Once you've committed, you can always ask, but the game's over.