Perhaps at the top of the free agent heap in the outfield is Upton. Going into the offseason, it appeared a six or seven year deal worth over $150 million was entirely possible. At this point, that seems to have been a generous estimation. Upton is still a solid, above-average major leaguer, but he may never live up to the expectations that were forced upon him in his teenage years and that have followed him since he was drafted. Upton will obviously get a contract for next season, but it may not be for the money he expected. For Upton, it may make the most sense to take a “pillow contract,” otherwise known as a one-year deal, especially given the weak free agent market next offseason. With the Orioles focused on both Chris Davis and Yoenis Cespedes, and the Angels apparently unwilling to spend, the Rangers may be the most likely fit, especially on a one- or two-year contract.
Potential Fits: Texas Rangers/Baltimore Orioles/Los Angeles Angels
Prediction: Texas Rangers
If Upton is A-1 on the free agent outfield market, Cespedes is most clearly A-2. The only real knock against Cespedes when it comes to contract talk is his age, given that he is a few years older than Upton and thus a few years closer to his decline years. With a deal in the five- or six-year range, it is likely that Cespedes’ next contract will take him into his decline years. That has made quite a few teams wary of giving him beyond a two- or three-year contract, which has been discussed by a few teams, including the Chicago White Sox. Cespedes may be inclined to take a shorter term deal if the big contract does not work, but it appears likely that his market is still strong enough to get him in the $100 million range. Despite the need, the Angels do not have the money to spend on Cespedes. The White Sox appear to be a good fit, but they seem unwilling to go past two or three years on a contract. That leaves the Baltimore Orioles, who seem increasingly frustrated with the Davis negotiations, and see Cespedes as a better alternative than Upton.
Potential Fits: Baltimore Orioles/Chicago White Sox/Los Angeles Angels
Prediction: Baltimore Orioles
While going into the offseason Upton, Cespedes, and Jason Heyward were in a tier of their own at the top of the free agent outfield market, one tier below them were several other players, including former Chicago Cubs center fielder Fowler. Fowler is coming off one of the best, and more importantly most consistent, years of his entire career. With the signing of Heyward, the Cubs made it pretty clear that they considered Heyward capable of playing center field, which left Fowler unlikely to return. However, even so, the fit still makes sense especially if the Cubs end up trading Jorge Soler at some point in the immediate future. It remains unlikely though, which makes the most logical fit for Fowler the other Chicago team, the White Sox. His acquisition could push Adam Eaton to a corner position and push Avisail Garcia to the bench, significantly improving the team both offensively and defensively.
Potential Fits: Chicago White Sox/Chicago Cubs/Texas Rangers
Prediction: Chicago White Sox
While the players mentioned above occupy the top two tiers of free agent outfielders, there is a third tier behind them, occupied by Jackson. Jackson represents an interesting outfield option this offseason. Coming off a season in which he was traded midseason and rebounded slightly, Jackson has rebuilt at least some of his value. Jackson is still young enough to bounce back further and could provide countless teams with some good outfield depth. Despite the cheap price, the only two logical fits of teams that have shown some interest are the Cubs and White Sox. Given the Sox being big players for some of the bigger outfielders, Jackson makes the most logical sense as a fourth outfielder with the Cubs for next season.
Potential Fits: Chicago Cubs/Chicago White Sox
Prediction: Chicago Cubs