What Would I Buy w/ Tonight’s Powerball Jackpot?

I don’t play the lottery, I think it’s a foolish waste of money and time… well unless it gets to above half a billion dollars like it is tonight with the Georgia Powerball. I’ll throw down a couple of bucks on that and put my ethics and belief aside for greed, I am the Greedy Pinstripes after all but I digress. Let’s just throw a nice round number out there, after taxes, and assume that if I won tonight’s drawing I would take home $500 million in cash. If I were running the Yankees what could I do with said winnings? And spoiler alert, you won’t be calling me the cheap owner when it’s all said and done.

$500 million can buy a lot but I would want to be smart with it. Justin Upton is smart money and is easily the best positional player and best fit left on the free agency market. I personally like him more than I did Jason Heyward so if Upton wants $200 million Upton gets $200 million from me. At 28-years old and with the stats he has put up in pitching friendly parks in Atlanta and San Diego I think he will live up to the contract and then some. Upton hits right-handed, hits for both power and average, will take a walk, steals bases and plays some stellar and underrated defense.

My next thing to do would be to eat the contracts of Jacoby Ellsbury and CC Sabathia. I am personally big fans of both but honestly there is just better ways of spending your money than on oft-injured and under-performing stars. As a fan that hurts but on the business side of things it simply makes sense. I am reluctant to eat the Ellsbury deal with a shade over $100 million left and the Sabathia deal with around $50 million left but that’s business. It’s six of one and a half dozen of the other if you’re paying them on the disabled list anyway. With my final $150 million I would throw a contract to a starting pitcher and/or a relief arm. Wei-Yin Chen and Antonio Bastardo maybe? Chen and Doug Fister? Who knows what it would take but I would improve the pitching in some way, shape or form.

Releasing Ellsbury allows Brett Gardner to slide back into center field and Upton to slide into left field. Releasing Ellsbury and adding Upton balances out a very left-handed heavy lineup and ultimately makes the lineup 100 times better in my opinion. Releasing Sabathia and adding a proven AL-East veteran and bullpen arm finishes out the roster and the pitching staff and all because I bought a stupid $2 lottery ticket and won the Georgia Powerball. You’re welcome Yankees family!