Before the SALT cap of $10K, it could easily matter. Prior to the cap, I itemized deductions every year - easy if you have a mortgage, live in a high income tax state, and both spouses work. In those days the standard deduction was $12K, and just our state taxes exceeded that amount - forget about mortgage + charity.

Even after the SALT cap, on some years itemizing was better.

And I believe as of next year (or the one after?), the SALT cap is going up significantly. Back to itemizing every year.