Wild Card

Wild Card Questions

85-year-old parents just sold their home

Hi Terry, My 85-year-old parents just sold their home of 55 years. Unfortunately, they never planned well for a retirement...

Best way to title vehicles for an older couple

Hi Terry, My wife and I are in our late 70s and have our 3 vehicles titles in seperate names,..

Making changes for protection

You had discussed on WGN radio about something that should be done on google to protect our (iPhone) security—could you..

Can I be classified as Head of Household for Tax Filing Status?

My adult son moved in with me in April, 2025. He has no money, no job and no prospects. I..

Online banking apps

Just bought a new car. Financed it through Kia Finance and signed up for their app, kiafinance.com. I’m planning on..

Annuity

I currently have an annuity that has a balance of 165,000. It is getting a 5.65% rate. It’s a 3..

I appreciated your report on WGN tv about the market today

I appreciated your reporting on the stock market falling this morning on the WGN morning show. I felt the segment..

Increase in Medicare Costs due to Real Estate Sale

I sold some property which increased my income for last year. It’s a one-off. SSA says that because of that..

Capital Gains

Hi Terry, am I to understand that I can cash in some long held stock and not pay Capital Gains..

Estimated Tax Payments

Need to make estimated tax payments. The IRS website says it is ok to write a check to the government...

Should I take offer Paramount’s offer to acquire my 35 shares of Warner Bros. Discovery shares

Good morning, Terry. I love listening to you on WGN and reading your columns. We acquired 35 shares of Warner..

Medicare cost after inheritance…

Hi Terry, my monthly Medicare cost triple this year because of a one time inheritance that was on my tax..

Recently widowed

I’ve just filed with the SSA for survivor’s benefits. My husband passed in October. SSA has no W-2 from 2013,..

Medicare fraud

My husband has been charged on his Medicare account for intermittent catheters at the cost of $12,000 over two separate..

Government taxing IRA,401K,RothIRA

Saw a rather disturbing video on email that was warning retirees to move on securing their accounts because the government..

SIM card

Dear Terry I always enjoy reading your articles and financial advice . Last Sunday you mentioned SIM card protection so..

SUM Theft in the Chicago Tribune on Dec 21, 2025

Is the SIM protection code you mentioned different from a PIN I have created before I can use my phone?..

INHERITANCE

I HAD A SIBLING WHO PASSED AWAY DECEMBER 2024. THERE WAS A WILL, HOWEVER NOT UP TO DATE. WE ARE..

Crook County property appeals

Hi, Terry, can you recommend a trustworthy person who can help my elderly parents appeal their Crook County property taxes?..

Gold

I just heard you on WGN radio and you gave a name where you have bought gold and I missed..

money

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