Chicago Cubs are failing in one key regard of roster management

This part of the Chicago Cubs overhaul was supposed to be about not only developing young players but also inking them to long-term extensions.

Last Friday marked the deadline for teams and arbitration-eligible players to exchange salary figures. Players are arbitration eligible for their fourth, fifth and sixth years of Major League service or if they are within the top 22 percent of service time for second-year players (so-called Super-Two players).

Kris Bryant and Addison Russell were Super-Two players last year. Carl Edwards Jr. is a Super-Two player this offseason by exactly one day. Yes, that’s right if he had one less day of Major League service time he would not be arbitration eligible until next year, his third season in the bigs.

Players make more in arbitration than they do during their first two or three years of service time. In their rookie year, players make the league minimum. In their second year (and third if they are not Super-Two) teams and players try to come to an agreement. But if they don’t come to said agreement the team gets to pay the player whatever they want.

Last year, Ian Happ was the first player the Cubs were not able to come to such an agreement with since Theo Epstein took over the Cubs front office. Reaching an agreement on compensation during a player’s second and third years in the Major Leagues can be an important point in maintaining a positive relationship between the team and the player.

In 2016 Gerrit Cole was unhappy with the deal he got from the Pirates. Fortunately, on Happ’s end, he understood the business aspect of the game.

“There were no issues, no hard feelings,” he told the Chicago Sun-Times. “The guys upstairs do a great job of treating players the right way.”

Trying to treat players the right way during this process is the reason the Cubs paid Bryant $1.05 million in his second season when they didn’t have to.

Teams and players can avoid arbitration by signing a contract before the arbitration hearing. The Cubs front office likes to do this because you can rub a guy the wrong way via the adversarial process of the arbitration hearings. Teams argue the player should get paid the lower of the two salary requests. The player’s agent proposes for the player to get paid the higher of the two figures. Last year, things between the Yankees and Dellin Betances got so contentious that both sides complained publicly about it.

Chicago Cubs: Taking care of the guys on the field

Since Epstein took over the front office, the Cubs have only gone to arbitration once. That was last year with Justin Grimm. And that was only over a difference of $275,000. The arbiter picked the Cubs $2.2 million over Grimm’s $2.475 million.

Recent years have added another complication to the arbitration process. It used to be that teams would continue to negotiate with players on possible contract extensions right up until the actual arbitration hearing. Now all 30 Major League teams have adopted a “file and trial” approach. That means that if an agreement on a contract extension hasn’t been reached by the time salary figures are exchanged then they stop negotiating and just wait to go to arbitration.

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Sometimes pressure from these arbitration deadlines cause players and teams to not just negotiate one-year deals to avoid arbitration, but multi-year deals instead. Last year to avoid arbitration Pedro Strop signed a one-year deal with a club option for 2019. That’s as mini a contract extension as technically possible, but that option year (which the Cubs picked up earlier this offseason) is the reason we aren’t currently sweating out Strop’s free agency.

This year the Cubs reached agreements on one-year contracts with all of their arbitration-eligible players. Now it is possible that players and teams could turn right around and tear up the one-year deals that they just signed to work out much longer multi-year deals. Or they could even reach a deal in the middle of the season. Starlin Castro signed a seven-year contract extension with the Cubs in August 2012. Anthony Rizzo signed his contract extension with the Cubs in May 2013. However, the arbitration deadline is when most contract extensions with players under team control historically get worked out.

These contract extensions usually end up being very team-friendly. These are young players signing away the prime years of their careers before they have reached the peak of their abilities. Teams are taking a bit of a gamble that the players won’t suddenly lose it. And the teams are expecting the players to continue to improve over the course of the term of the contract. But overall these are low-risk, high-reward contracts for teams.

Anthony Rizzo’s current contract is arguably the most team-friendly contract in all of baseball. It is a seven-year contract with team options for an eighth and ninth year. So it will likely end up being a nine-year, $73 million dollar deal once all of the options are picked up and all of the escalators in the contract are reached.

Jose Quintana is the only other Cub who is currently on a similar contract extension. The front office’s inability to sign any more of their young players to contract extensions is the biggest threat to this current competitive window of Cubs baseball closing. At least some of the young players signing contract extensions were supposed to be part of the plan.

But if you were a young baseball player, would you look at Rizzo or Quintana’s contracts and think to yourself that you wanted to sign up for something similar? The reason to do so is to lock in tens of millions of dollars in life-changing money when you were making only hundreds of thousands of dollars.

Chicago Cubs: Who will sign and who will test the waters?

If players had already gotten some big money in the form of signing bonuses that make the life-changing money argument a tougher sell. Of the Cubs’ seven arbitration-eligible players this year all of them except two (Kyle Hendricks and Carl Edwards Jr. were first-round draft picks who got significant signing bonuses. Hendricks was a 39th round pick and Edwards was a 48th round pick.

Hendricks was a Cy Young finalist in 2016 and is just barely 29 years old. So the Cubs should be trying to sign him to an extension. However, this is Hendricks’ second year of arbitration. So he is already starting to earn millions of dollars. The right-hander could be a free agent after just two more seasons. So he may now be thinking he’s so close that he should just wait until he is a free agent to sign his next contract.

Edwards, on the other hand, is a candidate to just lose it. When he is right he is one of the best setup men in baseball. But after losing his control late last year Edwards is one of just many questions in the Cubs bullpen.

Arbitration contracts are not guaranteed until Opening Day. A player on an arbitration contract can be cut during Spring Training and receive either 30 or 45 days termination pay, depending on when during spring training they are cut. That is what the Cubs did with Grimm last year. I’m not saying the Cubs will eventually cut Edwards during camp, but its a nice option to have with players who are on arbitration contracts. It’s also nice to be able to go year to year with players whose talents are as volatile as Edwards and Grimm.

Kris Bryant, Javier Baez, Kyle Schwarber, Mike Montgomery and Addison Russell were all first round picks. As such, they all received significant signing bonuses after they were drafted. So far none of them have signed extensions.

Bryant is especially unlikely to sign a contract extension. Scott Boras is his agent and is known for taking his clients to free agency. Bryant is already earning millions of dollars in salary even before he becomes a free agent. His arbitration and pre-arbitration salaries are breaking records. The 2016 National League MVP has also earned significant sums of money from endorsement deals with companies such as RedBull. Bryant even had an Addias billboard that read, “Worth the Wait,” across the street from Wrigley Field before he had even made his Major League debut.

After his MVP runner-up season, signing Baez to a contract extension would be even more expensive and less likely than it was a year ago. But consider for a moment the bargain that the Milwaukee Brewers got on Christian Yelich‘s MVP performance. Yelich signed a seven-year, $49.5 million contract back in 2015. So the Brewers only paid about $7 million for last year’s National League MVP.

Chicago Cubs: Current labor situation hurting extension chances?

Making contract extensions even less likely is the current labor situation. MLB spent less on player salaries in 2018 than the year before. Free agent contracts are getting shorter. Jake Arrieta is warning young players. One agent is even hoping, “Every damn agent holds the line,” in regard to the arbitration process.

For instance, compare Yasmani Grandal‘s recent one year contract with the Brewers to Russell Martin signing a five-year contract with the Toronto Blue Jays in 2014.

The most likely candidate for a contract extension is Contreras. The rest of the Cubs’ young players have already begun to earn life-changing money. However, these types of extensions are becoming rarer and rarer both amongst the Cubs and around baseball in general.

This competitive window has probably already been shortened by the lack of contract extensions. But perhaps an extension or two can still be worked out. That would help to prompt open the competitive window a little bit longer.