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How do the Cubs get to the next level of contention?

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Can they approach the level of consistent excellence the Dodgers currently inhabit?

Photo by @WillByington /

As the ball landed, an era ended. Anyone watching dispassionately probably knew it. As Kyle Schwarber's ball landed in the Allegheny River after a Gerrit Cole pitch the Pirates were rebuild-bound. Unable to afford free-agents to fill their comparative weaknesses, it became very bleak for Pittsburgh. Are the Cubs to the point where they can largely avoid the boom/bust cycle?

The Los Angeles Dodgers have won seven NL West crowns in succession. They’ve clinched a postseason spot and figure to win the 2020 division title as well. Nobody seems to be asking when the Dodgers’ window of contention will be over. Even if the Padres catch the Dodgers by 2021, LA figures to remain competitive. Their pipeline is envied, and their player development is top notch. Their spending is among the top few in the league every season. Rarely do they prioritize one campaign over future seasons. As such, they often retain their young talent for future runs, trading pieces they consider more disposable. Can the Cubs get to that level of competitiveness?

One of the problems with discussing the topic is some have a bit of a conflict of interest, so to speak. For instance, some fans are Javier Baez fans enough that anything hindering Baez from being a Cub for his entire career is fiercely battled. The premise of "valuing youth" is perceived as a slight against Baez (or Baez staying around), and is fought as if the Cardinals were getting three competitive balance picks every season.

The Dodgers' talent development pipeline isn't created to specifically "run off" any player. If it turns out the young third baseman they have is good enough to replace the current guy (at a lower rate), the older player (who likely has perceived value) is considered a potential trade piece. Since the Dodgers’ current roster is usually loaded, they might trade the veteran for prospects, if the offer is right, retooling on the fly.

Most Cubs fans remember getting burned by a prospect in the past. Perhaps you thought Jerome Walton would replicate his rookie season for a decade. When it didn't happen, the sting remains. What's hard to argue is that the Cubs had four pre-arbitration players in 2016 that excelled, and Anthony Rizzo only made $5 million that season. Getting stellar production from young players is useful for any team.

With the often polar mindset of "either/or" being so in vogue these days, a possible reaction to the success if youth in 2016 can be, "Why do you hate players getting paid?". I don't, but I realize that it is possible to develop talent better to push players at the levels of development that will still exist.

For instance, before the trade deadline, the Toronto Blue Jays were scouring the league for pitching. The Dodgers made available Ross Stripling. The Jays added Stripling, who the Dodgers didn't really have room for, anyway. Among the players to be named later was Kendall Williams, a 2019 second-round selection.

As to whether Stripling or Williams produce or not for their current teams, the Dodgers added quality for an extraneous piece. That seems a desirable situation to get into for any organization. It has nothing to do with running off popular players. It has to do with having more excess quality than most teams.

I'm surprised at the quality of depth the Cubs currently have on their 28- and 40-man rosters. As savaged as the off-season was for the low-rent free agent signings, Jason Adam, Dan Winkler and Ryan Tepera might be worth keeping around for 2021. Duane Underwood Jr. and Alec Mills have taken steps forward. Colin Rea and Adbert Alzolay are on the path toward useful status. Add some good results from Tyson Miller, Cory Abbott, and Brailyn Marquez, and the Cubs could be developing pitching without buying it in free agency.

As to when you know the Cubs are getting there? If they get to the point where they have a relief pitcher (or any other player asset) with the parent club that other teams covet, but the Cubs no longer has a need to retain, they're getting close. For instance, if Adam's recent success and potential future career arc is "good, but not better than what's being idled in Triple-A,” they're close.

The Cubs eyes are mainly on the Cardinals for 2021. The Reds, Brewers and Pirates appear to have some rather significant holes. Contention isn't exclusively about free agency status. It's about being competitive in the division, and having quality almost ready from the pipeline. How soon will Brennen Davis and Miguel Amaya be ready to contribute? Will the secondary prospects step up? Will the international prospects translate stateside? Getting better every month seems a bit trite, but if the organization is better dealing with this trough than others, ground made up will show up, eventually. The opposite can also be true.

The Cubs aren't exempt from downturns yet. If the players developed internally appear more useful than free agents, the desired destination is near. Adding to the annual playoff pool might keep the Cubs even more in contention in the in-between years. Mind who you think are the weakest hitter and pitcher on the 40-man roster over the off-season. If a designated for assignment player appears better, endorse filing a claim. If that's rarely the case, the Cubs may finally be approaching an enviable 40-man roster. And more regular contention.