Last week, New York Yankee shortstop and future Hall-of-Famer Derek Jeter played his last Major League Baseball game. He chopped a single to third in the third inning to drive in a run, then took himself out for good. That final hit brings his total to 3,465 hits, along with a .310 batting average, five Gold Glove awards, and five World Series rings. Jeter was that rare player who stayed with a single club for his entire career. He’s also untainted by so-called “performance enhancing drugs” plaguing the game (or, in the case of Jeter’s teammate Alex Rodriguez, you can leave off “performance enhancing”). Jeter goes out a very popular guy — and that popularity is about to send him into extra innings with our friends at the IRS.

Jeter earned over $265 million over the course of his 20-year career. And that’s before his endorsement deals with Gatorade, Fleet Bank, Ford, VISA, Discover Card, Florsheim, Gillette, Skippy peanut butter, XM Satellite radio, and even his own Nike shoe. If ever there were a guy who could buy anything he wanted, it’s “Captain Clutch.”

But that didn’t stop the baseball world from showering him with gifts upon his retirement. The Tampa Bay Devil Rays gave him a custom-painted kayak that cost more than $6,000. The Cincinnati Reds gave him framed autographed jerseys of fellow shortstops Dave Concepcion and Barry Larkin, along with three photos from the weekend in Cincinnati when Jeter was named captain of the Yankees. The Seattle Mariners gave him a seat from the Kingdome, where he made his major league debut on May 29, 1995. Even the lowly Chicago Cubs, which hosted Jeter for just five career games, honored him with a number from the hand-operated scoreboard. All told, the gifts are said to be worth about $33,000.

So, naturally, Jeter will owe another $16,000 or so in tax on those gifts. That includes 39.6% federal income tax, 3.8% Medicare tax, plus whatever state and local taxes apply where he receives the gifts.

Wait a minute. We’re talking gifts here, right? How can Jeter owe income tax on gifts?

It all comes down to why the giver makes the gift. If a gift is made out of “detached and disinterested generosity,” like when you give your children a birthday present, the officials in charge of collecting income tax generally turn a blind eye. (If the value of gifts to any single individual exceed $14,000 per year, the officials in charge of collecting gift taxes start getting interested.) But if the gift is really a marketing gesture in disguise — like when a team hosts a ceremony to present Jeter with his gift, then uses it as part of its marketing — that “gift” becomes taxable income.

What could Jeter do to avoid the tax? He could refuse the gifts, which wouldn’t seem very sporting. Or he could request they go to his charitable foundation. But that would defeat the purpose of gifts like the Cincinnati shortstops’ jerseys that are intended to be sentimental rather than valuable.

Jeter’s final-season salary was $12 million, which works out to about $74,000 per game, or $8,230 per inning. So the good news is that the tax on the gifts should only eat up a couple of inning’s worth of income.

Are your business associates planning to lavish you with gifts this holiday season? Call us. We know you won’t be happy to pay tax on them, but at least we can help you with a plan to pay the least amount allowed. And remember, we’re here for the rest of your teammates, too!

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