By making your charitable contributions with long-term appreciated assets instead of cash, you will receive a charitable deduction for the full fair market value of the assets gifted. Even if you have a low basis in the assets, you will still receive a charitable deduction for the full fair market value. When the charity liquidates the assets, it will realize all the built-in gain. Because charity selling the assets is tax exempt, it will owe no taxes on the gain.
In contrast, if you liquidate the appreciated assets and then make a gift of the cash, you will owe taxes on the built-in gain. When possible, it is almost always better to make charitable gifts with appreciated assets.
By way of example, imagine you own 10 shares of Amazon stock with a basis of $1,000 per share and a fair market value of $3,000 per share. If you gift those shares to a charity, you receive a charitable deduction for $30,000. If you sold those shares and used the after-tax proceeds to make the donation, you would owe taxes on $20,000 of built in gain. After paying taxes at 23.8% (cap gains + Net Investment Income Tax) on the gain, the amount going to the charity is $25,420. Yes, you could use your $25,420 charitable deduction to offset the taxes you paid, but why? Instead, gifting the shares directly to the charity places you and the charity in a better position.
When making gifts of appreciated assets, your ability to use your charitable deduction each year will be limited to 30% of your adjusted gross income for that year. For many individuals, this limit will not be an issue. If your donations of appreciated assets each year are more than 30% of your AGI, you can carry the unused charitable deductions forward to future years.