Winning A Trump Tower Condo Not So Great For Staff Assistant

Winning A Trump Tower Condo Not So Great For Staff Assistant

I just read the Tribune article about Deborah Robertson, a Baltimore staff assistant for the Social Security Administration, that just won a condo in the Trump Tower in an HGTV contest. My first thought was that her excitement is very short lived.

Of course she is delighted right now. After all, the Trump Tower is a spectacular building. But, the condo is worth $750,000 so she is about to find out what it really means to now be in the top 1% and “rich”. Her income tax liability will be $239,814 + 35% of whatever else she is going to make this year. Since she is a staff assistant and lives with her sister I think it’s safe to say that she doesn’t have this money and it will be due by April 15.

Second, she is now liable for a $560/month assessment.

Third, her annual property taxes are going to be around $11,250/ year.

Oh…and she doesn’t even live in Chicago. Is she planning on flying out here on a regular basis? The cheapest Southwest fares are $273 round trip. Is she going to move here?

I dunno. She’s pretty excited about winning this place right now but when reality sets in she’s going to realize that she needs to dump this place ASAP. If she does she can find herself with almost $500K in the bank. Now that’s good luck! Unless of course she decides that she needs to use a celebrity realtor to sell her place, in which case she’s likely to spend $45,000 in commissions.

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Tags: Taxes, Trump Tower


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  • Per rule on the contest,,

    "In lieu of taking title to the HGTV Urban Oasis Home, Grand Prize Winner will have the option of receiving $675,000.00 in cash."

    If she's smart, the cash decision ought be a no-brainer.

  • In reply to Jeff:

    Interesting. They set that number so that it works out to be pretty equivalent to taking the place and selling it overnight. She saves on commissions and closing fees and also saves a bit on taxes by not paying taxes on the commissionable amount.

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