The first step we'll take in determining which franchise is in the better long-term position is by looking at albatross contracts. Who owes whom the most money over the longest period of time?
The highest-paid player on either side should be obvious to readers of this or any other Cubs blog: it's Alfonso Soriano, who's owed another $57 million between 2012 and 2014. For all the crap Sori gets about his contract, it's important to note he's still an above-average player, and actually probably will be for the duration of his contract. But there's a massive difference between "above-average" and "worth $57 million," and there's no doubt the team is overpaying him.
Elsewhere on the roster, the Cubs have already committed to paying $72.6 million to a handful of players in 2012, including Soriano. Like Alf, Carlos Zambrano is owed $19 million, while Ryan Dempster will be paid $14 million. Recently-extended Carlos Marmol is owed $7 million, Marlon Byrd gets $6.5 million, and Sean Marshall will make $3.1 million, while Aramis Ramirez and Carlos Silva (!) will each likely be paid $2 million to buy out option years.
The only Cub player not named Alfonso that has been guaranteed money after 2012 is Carlos Marmol, who will be owed another $9.8 million in 2013.
On the other side, there is the fact that the White Sox don't owe any one player $19 million annually until 2014. That said, the South Siders have much less financial flexibility respectively, with nearly $95 million committed to player salaries in 2012.
The team's three highest-paid players -- Jake Peavy ($17M), Adam Dunn ($14M), and Alex Rios ($12.5M) -- are hardly guaranteed to be worth the money. According to Fangraphs, that trio has combined to be worth roughly zero wins above replacement so far this season. Surely all three are talented and could yet bounce back, but Jerry Reinsdorf can't be too happy about owing Peavy, Dunn and Rios a combined $104.5 million between 2012 and 2015.
On top of that, the White Sox will pay Paul Konerko another $25.5 million over the two years after this season, plus Alexei Ramirez is guaranteed $32 million over the four years following the 2011 season. Both players are very good and could be worth the money, but the deals are worth mentioning in a conversation about long-term financial capabilities.
The Cubs have the highest-paid individual player of the two teams on their roster, but the NL team has much more flexibility after the 2012 season, with just $28 million in committed salary on the books for 2013, and $19 million in 2014. This apparent advantage could evaporate quickly if the Cubs acquire, say, a veteran first baseman in free agency, and agree to pay him gobs of money over an extended timeframe. But for now, I think the Cubs have the advantage here.
Better Long-Term Financial Flexibility: Cubs