Since you have to exercise ALL the options within a year, it really doesn't matter which one your exercise first! I would exercise the last ones FIRST in hopes that some of them would get long term treatment.

"Stock options" covers a lot of ground. I'm assuming, based on inferences in the wording of your Q, that these are "naked call" options, which give you the option to purchase stocks at specified prices on or before certain dates, or the option/s expire worthless, with absolute zero value on the close of the market at the specified date. And though you say "5000 stock options", I'm thinking that this is probably 50 "option contracts", each contract covering 100 shares. If these are 'normal' call options and you own them outright, with no restrictions on their use (other than those in a normal options contract), then you don't necessarily have to "exercise" them by buying the underlying stock. There is a very strong options market by its own-self. That is, you can sell the option at any time before the contract expiration period. Calls that are "in the money" (where the strike price is already less than the listed price of the stock on its home exchange) can be enormously profitable and will enjoy highly leveraged appreciation in value -- up to the contract expiration. That contract expiration date will kill you, though. You MUST pay attention to that. Talk to a broker. You may be sitting on a gold mine -- which will turn into a pile of shit after 4:30 PM Eastern Time (US) on some Friday. But offhand, and all other things being equal, and if I were going to exercise the options to purchase the stock, then the ones to exercise first would be the ones that are "most in the money". If instead you're talking about stock "warrants", which are another kind of option entirely, then the advice above is more or less meaningless, because a warrant is a different instrument than an option. I think you need to have a serious talk with a stock broker. Good luck.