Bolded - Yet since he'll be entering FA as a CF he'll ask for CF money. The contract could/should easily top 100 million because of that positional value, which I'm sure he and Boras have already thought of. 1 - Upton's a better fielder, better base runner, slightly better base stealer, and is a competent offensive player in his own right. He's a significantly better glove at that IMO, and I have no questions about his ability to man CF in the short and long term. He's one of those gliders who makes it look lazy (which is the new easy since people like to see a good gritty effort). Kemp delivers those good gritty efforts by diving, but they'd be unnecessary if he was a better defensive CF. 2 - Upton plays for a team that consistently overachieves rather than underachieves year in and year out. Not all that significant in today's numbers driven world, but something that I put some value in. 3 - Upton's 2007 wasn't a complete fluke. This was a player, a former #2 overall draft pick and top tier prospect, who was playing up to his true talent level. It was within the realm of possible outcomes. The problem is that after that he hurt his shoulder, and his game got untracked a little. We're seeing his LD% go back to what it was before the shoulder injuries (it's over 18% for the first time since '08), he's working with a BABIP (.272) a good 50 points off of his career BABIP (.324), and he's also playing half his games in a pitchers park in the AL East in a severely diminished run environment (the run environment will also drive Kemp's price up given his season). - Upton is a prime change of scenery candidate. He's hitting .170 at home this year, and that's just the number I'm using. The guy is one of many who absolutely hates playing and hitting in Tropicana Field. The place is truly a dump, and he's one of the players who's let it be known that he thinks so. This isn't about saving money to me at all, at least not in the way you're painting it. It's about getting bang for the buck. I've always wanted the Cubs to be one of those teams who buys low on high end talent if its there. Upton is that kind of player to me. I also just don't buy that Kemp is the kind of player I want to see the Cubs give 100+ million to. He's very good, but it takes more than that for me to want to see my team spend money like that on you. Soriano was a good, even very good, player when we gave him his money. That's not to say that Kemp is going to go Soriano on his big money deal, but as a future/probable COF who'll be getting CF money he'd be off to a good start. No, really I expect that size and power will start taking over his game when he gets his big money contract, and he'll gain big there while dropping his speed and defense. He's a very big dude as it is and that makes him a candidate to lose his CF speed earlier than BJ (and it's already worse). I don't see him as THE GUY, and landing and then paying him would make him just that. I'd much rather give 5/50-60 to Upton than the money and years Kemp will command. I could see Upton throwing up at least a couple .270/.350/.450 seasons in his prime with top of the line CF D and 20+ SBs a season at a good rate. I'd like to get in on that while more desperate teams are throwing their money at Kemp. Hopefully by the time the Cubs are looking for an OF bat they'll have landed another player teams will be desperate for, one of the 1B Pujols or Fielder. Of course with one of those guys Kemp makes a whole lot more sense too...For now my thought is buy the 1B, surround him for home grown and outside bargains, buy a TOR type pitcher or two in the next couple of years, and go from there. So many words.