For starters, is Boston's farm system sufficiently deep? Detroit is sure to demand a hefty package of prospects. Clay Buchholz, Michael Bowden, Daniel Bard, Ryan Westmoreland, Casey Kelly, Lars Anderson – no one is off limits when you're dealing for one of the elite sluggers in the game. How much talent can the Red Sox afford to give up?
How big are their wallets? Cabrera is about to enter the third year of an eight-year, $152.3 million contract. He's got around $126 million left on the deal, which will keep him fat and happy through 2015. Cabrera's 35-homer power won't come cheap.
How much does character matter? Cabrera is just two months removed from an ugly domestic incident with his wife that led to his arrest for drunken driving with a blood alcohol level of three times the legal limit. The night before a crucial one-game playoff, no less. Is this the kind of guy the Red Sox want in their clubhouse?
All of the above are valid questions. And they're questions that any GM in baseball, including the Red Sox' Theo Epstein, will be asking themselves this winter before they do anything too crazy. But at the end of the day, the Red Sox are the one team most likely to pass the Cabrera test.
If you're looking for a major league owner willing to fork over nine figures to pay Cabrera, then look no further than John Henry. In fact, it was Henry who first discovered Cabrera over a decade ago. Now he has a chance to bring the slugger back.
Upon first purchasing the Florida Marlins in 1999, Henry's front office found Cabrera, a 16-year-old kid in Venezuela blessed with raw power, and jumped at the opportunity to bring him to the States. Henry threw down $1.8 million, an unheard-of sum of money for the teenage phenom, and Cabrera was in the major leagues four years later. He became a superstar almost overnight.
Henry and Cabrera have long since parted ways. The owner left South Florida in 2002 when he sold the Marlins and entered into a deal to purchase the Red Sox alongside Tom Werner. The slugger skipped town five years later, when a blockbuster trade sent him from Miami to Detroit.
But back in the day, Henry saw something in Cabrera. He knew what he was looking at — a kid blessed with incredible talent. And in a lot of ways, that's what Cabrera still is.
It's hard to believe after a decade in professional baseball, but Cabrera is still only 26. He's still coming of age, both as a baseball player and as a man.
Does he have character issues? At the moment, it's easy to say yes. Cabrera's messy legal troubles over the past two months have cast him in a negative light, and front offices around baseball have taken notice. But back in 1999, John Henry saw a kid with potential, a young man waiting to mature. Perhaps he still sees it.
Is he worth the money? The Red Sox can't say no. This is the same team that offered Mark Teixeira $170 million. They dangled $160 million in front of Manny Ramirez to lure him away from Cleveland a decade ago. The Sox are no strangers to paying big money for big sluggers. And Cabrera is that kind of slugger.
He could be worth the prospects, too. After all, he's 26 — not much older than Buchholz, Bowden or Bard. And with Cabrera, you're looking at a sure thing. You're looking at one of the best in the game.
There are a lot of questions surrounding Miguel Cabrera. But there are also a lot of very encouraging answers. Cabrera could be the next big thing in Boston.