Justin Upton is open to signing an extension with San Diego Padres

Justin Upton will head into his first season with the San Diego Padres facing the same challenges that any player rapidly approaching free agency may see. The 27 year old has yet to experience free agency in his career and seems likely to reach that point a year from now, but that is hardly a certainty. Upton’s agent, Larry Reynolds, has told MLB Network’s Jim Duquette, that they are open to discussing an extension with the Padres – provided that talks take place before Spring Training begins.

There has been zero indication from the Padres what they plan to do regarding Upton’s upcoming free agency. It’s clear that the Padres are making every effort to field a competitive team in 2015. They’ve been one of the more active teams of the offseason, but there have been few revelations about how they intend to approach things beyond this year. Knowing that Upton was only under contract one more year – at $14.5 million for 2015 – the fact that San Diego was willing to pay such a steep price to acquire him – parting with four prospects – suggests that the team was, at the least, hopeful that a deal could be reached between the two sides at some point in the coming months.

The timeline suggested by Reynolds, however, could prove to be an obstacle.

There are roughly seven weeks before Spring Training camps will open, not including players who may choose to arrive early – be it because they are finishing up rehab from an injury, are joining a new franchise, or simply want to get the extra work in. That window is not a significant one, particularly where the two sides have yet to get to know eachother.

Upton doesn’t know how he’s going to fit into the team’s clubhouse or whether he’ll like playing in San Diego. The team has yet to learn what his work ethic off the field is like or whether the confines of PetCo Park will wreak havoc on his swing (thought he’s a .291/.359/.541 career hitter with 10 home runs in 46 games at the park). There are plenty of questions yet to be both asked and answered.

Of course, it also remains to be seen just how willing the Padres are to opening up the checkbook. Despite how active the team has been in recent weeks, they’ve primarily utilized the trade market to reshape their roster and have avoided tacking on any significant contracts beyond Matt Kemp‘s. With the Los Angeles Dodgers paying roughly $32 million of what Kemp is owed, that leaves the Padres on the hook for just $75 million. Upton will presumably look for a deal well north of that.

B.J. Upton, the elder Upton brother, signed a five year, $75.25 million deal with the Atlanta Braves prior to the 2013 season. He had just finished his age 27 season, batting .246/.298/.454 in 633 plate appearances for the Tampa Bay Rays – adding 29 doubles, 28 home runs, and 31 stolen bases. Through that 2012 season he’d accumulated a total of 15.4 bWAR.

Justin is entering his age 27 season this year. He’s a .274/.354/.476 career hitter who has averaged 33 doubles, 26 home runs, and 15 stolen bases a year. He’s accumulated 20.0 bWAR to date in his career.

There’s no easy comparison between the two brothers. They are both similar and different players on both sides of the ball. Justin has beat out his older brother in a number of milestones, however. He was one pick earlier in the draft (Justin was #1 overall in 2005, B.J. was #2 overall in 2002). He also debuted at a younger age (Justin was 19 years and 342 days, while B.J. was 19 and 345). Justin also has a pair of Silver Slugger Awards and two All Star selections to his brother’s none. He appears likely be in line for a bigger contract, as well.

One year ago there were a pair of big-name outfielders signed on the free agent market to significant deals. Neither Shin-Soo Choo or Jacoby Ellsbury profile as direct compareables for Justin Upton. Choo was always more of an on-base threat, while Ellsbury had the combination of power spikes and much more speed on the bases. Choo and Ellsbury were both older in their free agent years than Upton could be (Choo was 30, while Ellsbury was 29). Each received deals that were seven years in length and between $130-153 million in total value.

Upton may not command $21.85 million a year like Ellsbury received from the New York Yankees or even the $18.58 million a year Choo will see from the Texas Rangers, but he certainly could be looking at more than the $15.05 million a year his brother is getting from the Braves.

A six or seven year deal, estimating a $17.5 million average annual salary, could bring a potential extension to $105-125 million in total value.  There’s no way to know what Upton will be looking for if he is to reach the open market or what he’d consider fair to sign an extension with San Diego before ever suiting up for a game with the team. San Diego has been aggressively reshaping their roster, but the organization has not, historically, been a big spender on the open market. Perhaps that too could change with a new front office in place, with Upton serving as the first face to this new regime.

Next: Wieters, Orioles have yet to discuss an extension