I don't think you can critique the health factor of an NFL wide receiver, and their longevity, then disregard the same questions with pitchers. Sure, football players get hurt rather easily. But I'm not so sure NFL WR get "career ending hurt" any more frequently than pitchers, in fact, I'd bet they don't. And you are kind of glossing over the "if he makes the major leagues" portion of the debate. If he goes to baseball, there is no guarantee he'll ever make the majors. If he goes to football, he's pretty much guaranteed to make the bigs in his first year, with the only exception being injury, or being so incredibly unimpressive that the team makes him inactive all year(they won't cut him in the first year of a deal that gives him such a signing bonus). I would say that if he's drafted in the top 20, it would be really hard for the Cubs to offer enough money to make him give it up. If he's later in the first round, it will still be hard, but a little more even (I think a WR taken in the mid 20's would get about $4-5m guaranteed). And if he's in the 2nd round or later, the Cubs should be able to win the up-front money debate. The second question, however, is how quickly he'd be able to sign his next contract. If he goes football, he could conceivably be onto his 2nd big money contract by year 3. If he goes to baseball, he will be lucky if he's making arbitration money by year 6 (3 years in minors and 3 years majors). He should also make far more up-front secondary income via the football route, with advertising, appearances and all that. None of this takes into account which sport he actually prefers, as I believes it's impossible to know. But financially, it comes down to this: Baseball offers the far greater longterm potential for earnings, provided he makes it through 3-5 years of the minors relatively healthy, then pitches pretty well for another 6 years in the majors. If he reaches his peak in either sport, he's going to make more in baseball. But football probably offers the greater short-term guaranteed money, as well as potential for his next contract, unless he drops to the 2nd round of the draft or lower. Then, it becomes more of a question. Assuming he does well in the pros, then he'd still be in-line to make much more over the short-term, but, if he's drafted in the 2nd or later, and struggles in the NFL, then he'll only end up with a few million guaranteed.