Written by Adam Burke

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BJ Upton’s five-year, $75.25 million deal signed this past week was yet another reminder of why the Indians can’t afford nice things. The amazing thing about the current state of Major League Baseball is that $15 million per season is market value for Upton. Yes, BJ Upton, off a season in which he batted .246 with an on-base percentage below .300, got a long-term deal worth over $15 million per season and, yet, it’s perfectly justifiable. If you want to understand why baseball economics are so flawed, this deal is a pretty good starting point.

As I said, that is market value for Upton. It’s not really up to me to decide if this deal is right or wrong, but that’s the going rate for a player of Upton’s skill set and value. He has stolen 30 or more bases each of the last four seasons. In spite of a batting average hovering in the .240s, Upton has posted an average OBP of .316 over the last four seasons. Not an elite figure by any means, but considering his batting average, a nice achievement. His power numbers have increased each of the last four years and he is a solid defensive player, in spite of a less than stellar 2012 season defensively.

That would make Upton the Indians highest paid player by around $7M (estimated arbitration award for Shin-Soo Choo is just shy of $8M). If this doesn’t explain why it’s really hard to win in baseball without abundant financial resources, I’m not sure what will. This is not an indictment on the Atlanta Braves, who opted for Upton instead of Michael Bourn, who may be more valuable at a similar price. It’s an indictment of the system as a whole – a system that sets small market teams up for failure.

Every offseason, we, as Indians fans, are stuck watching the developments around us and getting more and more depressed about our chances of being any kind of consistent contender. Another one of those dreadful periods in Indians fandom will likely happen next week as the Winter Meetings take place in Nashville, TN from December 3-6. Representatives of all 30 MLB teams convene to discuss pertinent issues with Major League Baseball, or so they say. It’s probably just a lot of Maker’s Mark drinking and bullshitting about baseball, while talking trades and taking jabs at each other. AKA, I’d love to be there.

Agents mill around waiting for the perfect time to give their sales pitch to a GM. The cream of the free agent crop gets talked about more than the slutty sorority girl at a frat house party. Trade rumors spring up as a result mindless chatter between two GMs that some national MLB writer accidentally overheard and reads too much into. It’s a great event for fans that are able to keep all of the media reports in perspective. Well, for fans of teams who have money, anyway.

As for us Indians fans, we’ll be the subject of a lot of rumors we don’t care to be a part of. While I, personally, believe trading Shin-Soo Choo, Asdrubal Cabrera, Chris Perez, and various others, is the best course of action for the organization, many are going to have a hard time coming to grips with that. Suffice to say, that’s probably the only Indians news we’ll hear about next week. General Managers of rival teams will be trying their best to poach the talent we have to offer. Tribe fans keeping up on the minutia of the Winter Meetings will wear out Baseball-Reference.com and Fangraphs.com looking up prospects that they have never heard of before as their names get brought up in trade discussions.

The roster could look drastically different by the time the calendar reads 2013. As it stands now, just five years removed from the 2007 ALCS run, the only Indians remaining from that team are Choo and Cabrera. Choo played just six games and had Tommy John surgery. Cabrera was an August call-up. In a small market like Cleveland, where contention is cyclical in nature, it’s not very shocking that just two of the 41 players that made appearances for the 2007 team are still around. That doesn’t make it any less disappointing.

As of now, for 2013, the oldest Indian would be recently-acquired Mike Aviles, who will turn 32 in March. As the roster stands now, if Choo is not traded, he will join Aviles as the only players in their 30s. Of course, the Indians will likely add a couple of bargain bin, past-their-prime free agents in February or March. But, this is going to be an extremely young ballclub. A somewhat experienced ballclub, as the Indians’ struggles have allowed them to expose their youngsters to Major League Baseball at a young age, but an extremely young ballclub nonetheless.

Two weeks ago, I picked out my top five starting pitcher targets for the Indians this offseason. So far, I’m holding off on the position players because it’s all contingent on whether or not Choo is traded. Having two gaping holes at the corner outfield positions is not good for the offense, nor is it good for the defense. From a pitching standpoint, however, the needs there are not changing anytime soon.

At this point, I think it’s important for fans to realize how difficult of an offseason this is going to be. Despite the hiring of Terry Francona, a proven manager with World Series rings, he signed up for a long, drawn out process. The turnaround will not be built in one offseason, especially one where the Indians look to be subtracting current Major League talent from the roster. If everything goes how I predict it will, this is an offseason that won’t be judged until at least 2015 or later. Short-term gains will be non-existent while long-term gains will be an unknown.

In fact, I’ve been spending my downtime watching other teams’ personnel moves. The Diamondbacks are reportedly close to answering their shortstop question by trading Justin Upton to the Braves in exchange for Andrelton Simmons.The Diamondbacks were reportedly interested in Asdrubal Cabrera. If a deal for Simmons does, in fact, happen, now they have an opening for an outfielder. Enter a Shin-Soo Choo trade possibility. The Cardinals, meanwhile, still need a shortstop and Cabrera would fit nicely. Both of these teams have what the Indians want – young, high-upside starting pitching.

With the Braves adding two Uptons, the Nationals will probably make additional moves. They already acquired Denard Span from the Minnesota Twins in exchange for solid pitching prospect Alex Meyer. They are reportedly going to make a run at Zack Greinke. Enter the Phillies, who are coming off a very disappointing season and could use an offensive threat like Shin-Soo Choo. Other National League contenders, like the Giants and the Reds, could also both use offensive upgrades. The Reds could certainly use Choo, while the Giants could use both Choo and Cabrera. As Isaac Newton’s third law of motion says, for every action, there is an equal and opposite reaction. That can also apply to baseball front offices. If your competition gets better, you should make a move to improve your ballclub as well. Similarly, with the Tigers getting Torii Hunter and improving their club, the favorite to win the division got even stronger. It would make sense for the Indians to have the opposite reaction and look to build for the future. The Indians have two of the more attractive players on the market and can capitalize on the needs of others.

In that regard, the Indians are actually sitting kind of pretty this winter. It won’t be pretty for the fans, who could be watching a very bad baseball team next year, but the top levels of a very mediocre minor league system could soon have some serious talent worth watching. The 2012-13 offseason is a microcosm of small market life in baseball. When top talent gets too expensive, or nears free agency, recycle it into quality prospects. Unfortunately, with the last attempt at this – Sabathia and Lee – epically failed. For the Indians to have any chance in the near future, this offseason cannot be a failure.

All of this has to be remembered as Indians fans are reading the reports coming out of the Winter Meetings. The big picture is what Indians fans must focus on this offseason, no matter how hard it may be.