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.