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Two deadlines converged Tuesday in a way that illustrated where the Chicago Cubs are in their rebuilding cycle. As anticipated, Willson Contreras declined the one-year, $19.65 million qualifying offer after his representatives surveyed the market for the All-Star catcher, adding yet another data point to what looks like an obvious separation between the free agent and the organization that originally signed him as a teenager out of Venezuela. Looking forward, the Cubs added four prospects to their 40-man roster, bringing it to 38 by protecting Brennen Davis, Kevin Alcántara, Ben Brown and Ryan Jensen ahead of next month’s Rule 5 draft.

So many things have to go right to build a championship team that you need a little bit of luck. The Cubs notably left Contreras exposed in the Rule 5 draft after the 2014 season, when he had not yet played a game above the A-ball level, and then watched him win a Southern League batting title in 2015 and emerge as one of the game’s top prospects. Contreras jolted the Cubs with his energy during the 2016 World Series campaign and established himself as one of the best catchers in franchise history. But after rounds of heavy trade rumors and sentimental goodbyes at Wrigley Field, it’s clear that the Cubs want to go in a different direction with their catching setup and would be content with draft-pick compensation if Contreras signs with another team as expected.

Contreras is not a Gold Glove defender, but he is a strong thrower, a good blocker and a hard worker with elite offensive skills and leadership qualities, particularly around players from Latin America. There are few catchers in today’s game who can match Contreras’ two-way abilities, overall resume and playoff experience in a big market. Perhaps the security of a long-term contract — after essentially going year-to-year since 2009 — combined with Major League Baseball’s rule changes will help Contreras grow as a receiver and enhance his value behind the plate. The Cubs are expected to add a veteran catcher — names such as Christian Vázquez and Omar Narváez have been discussed internally — who will share the catching responsibilities with Yan Gomes next season.

Brennen Davis (Daniel Shirey / MLB Photos via Getty Images)

For all the talk about the Cubs’ great 40-man roster crunch, the club took a measured approach to adding players before Tuesday’s deadline, a reflection of the talent pool and the challenges in carrying a player selected in the Rule 5 draft for an entire season. Instead of making a trade to open a spot on the 40-man, the Cubs actually traded a pitching prospect, Alfredo Zarraga, to the Tampa Bay Rays for infielder/outfielder Miles Mastrobuoni. Mastrobuoni, 27, is a left-handed-hitting versatile defender with just eight games of big-league experience and three options left. The move could make Zach McKinstry, who is out of options, superfluous, with the two effectively exchanging roster spots at some point this winter.

The Cubs did have a larger-than-normal group of interesting prospects to evaluate, but not that many players who are ready to contribute at a high level in the majors next year. Still, Davis, Alcántara, Brown and Jensen represent an infusion of young talent from recent draft classes and the sell-offs at the last two trade deadlines. But even now, the 40-man roster will continue to be fluid. Friday’s non-tender deadline could very well open up spots and it’s possible the Cubs will try to sneak some players through waivers with the hope of bringing them back as non-roster additions over the course of the winter.

More space has to be created, because ultimately, and most importantly, the Cubs will be aggressive in adding established talent to their roster this winter. Filling up their 40-man roster with players who will likely end up as depth pieces probably doesn’t make sense. All it does is force more difficult decisions down the line as they continue to add free agents or players via trade.

“Patience is always a really difficult thing, but it’s the thing that typically gives you more rewards in the end,” said Cubs general manager Carter Hawkins, who joined the organization 13 months ago. “I’m happy with our development structure. Our scouting process continues to improve. The young players in the system continue to improve. Outside of some unfortunate freak injuries, across the board, a lot of our top players made great strides. We see them impacting our major-league club here in the near future. You see the guys that are at the major-league level making some big strides. We still have a ways to go. We still have to make some pretty big leaps. But at the same time, the future is really bright for the Cubs.”

The Cubs weighed the risk of exposing some well-regarded players to the Rule 5 draft against clearing up some of those issues by forcing trades in order to get players they may not like as much. The risk is losing a player they do like — one they’ve put in a lot of work to develop — for nothing. The group of Cubs prospects who will be eligible for the upcoming Rule 5 draft includes: Chase Strumpf, Darius Hill, Jake Slaughter, Kohl Franklin, Riley Thompson, Cam Sanders and Luis Devers.

But those internal debates came to this conclusion: Sometimes, it can be overthinking things when making these decisions, especially in the context of today’s game. A player selected in the Rule 5 draft can’t be optioned down to the minors. Options are so valuable and teams use those mechanisms liberally, especially at the bottom of the roster. There are also limitations on the roster as teams are not allowed to have more than 13 pitchers at a time. Unless you love a player you selected — maybe a potential starting pitcher or an everyday position player — it’s hard to justify keeping an inexperienced reliever or bench player on your roster all season long.

That reasoning is only amplified by the fact that there don’t appear to be as many tanking teams entering 2023. Perhaps the Oakland A’s could be considered, but even they value options greatly and tend to try to turn things around faster than people expect. The Detroit Tigers are coming off a terrible season and are currently onboarding a new team president in Scott Harris. But would Tigers manager A.J. Hinch, who functions as a high-level executive as well, be up for a rebuild? While every team may not be “all-in” for 2023, fewer groups appear to be totally gutting rosters for the future. Meaning keeping a Rule 5 pick all season may not make much sense, so the Cubs didn’t necessarily have to force a player onto the 40-man roster.

Again, the narrative about this roster crunch was overblown. If the Cubs had so many good players, then they might have stayed in the playoff picture past May and won more than 74 games this year. In recent days, the Cubs formally released Jason Heyward and created more roster space by outrighting nine players who cleared waivers. While the Cubs have specific roster needs and preferences within groups of available players, the big idea in Jed Hoyer’s front office is that the team needs to significantly upgrade its talent levels in every area, and that overall strategy could take different forms over the course of the winter.

If fully healthy, Davis likely would have already made his Wrigley Field debut, but the Cubs can’t count on him to be their Opening Day center fielder next year when back issues wiped out most of his 2022 season at Triple-A Iowa and followed him to the Arizona Fall League.

Alcántara, the 6-foot-6 outfielder the Cubs acquired from the New York Yankees in the Anthony Rizzo trade, won’t turn 21 until next summer. Alcántara played in 112 games this year with Low-A Myrtle Beach, which can be a difficult offensive environment for hitters, and finished with 15 home runs, 85 RBIs, 14 stolen bases and an .811 OPS. With his exciting combination of tools, the Cubs believe he has star-level talent.

“Kevin has incredibly high upside,” Hawkins said. “He could be a dynamic player on both sides of the ball. He has legitimate plus raw power. It’s his continued ability to refine his approach. As pitchers start to expose some areas that he has weaknesses in, his ability to make those adjustments is really going to dictate his ability to reach his ceiling, which is really, really high.”

The Cubs see Brown, the 6-foot-6 pitcher the Cubs acquired from the Philadelphia Phillies in the David Robertson trade, as someone with two plus pitches in his four-seamer and slider. They’re expected to add to his arsenal this winter, perhaps a pitch with more depth. Brown was impressive in High A with the Phillies and continued to look strong once promoted to Double A following the trade to the Cubs. He’s a bat-misser with the type of stuff that’s suddenly become prevalent in the Cubs system, and team officials believe he’s only beginning his ascent as a prospect.

“Ben has power stuff and looks the part of a starter,” Hawkins said. “He has the multi-pitch mix to be able to do that. He’s performed well at the upper levels. I think amongst all of our starting-pitcher prospects, he’s certainly up there. He’s a guy that we expect to impact our club in the near future.”

Jensen, a 2019 first-round pick, is a great developmental story for the Cubs.

“He faced some adversity early in the year,” VP of player development Jared Banner said. “As a department we recommended to him the best course of action was to make some changes to his arm action down in Arizona. That’s asking a lot for a pitcher to leave his ballclub and leave active competition to go work on something. But it’s really one of our departmental focuses, that sometimes the best development doesn’t occur during games.”

Jensen bought in and for almost the entirety of May and into June, he worked on shortening his arm stroke in Arizona. The results weren’t perfect after his return, but the command improved enough for the Cubs to protect Jensen and his electric arsenal — a four-seamer that touches triple digits, a newer cutter and a hard, sweeping slider. The Cubs haven’t ruled out starting in his future, but it also appears that a multi-inning relief role could be coming as he continues to develop and his walk rate dips.

Davis should make his big-league debut next season, assuming he stays healthy and productive. Jensen has clearly put himself on the radar as a possible relief arm for 2023. Brown possibly has an outside shot to reach the bigs next season if he continues this trajectory. Alcántara is likely still a few years away, but his impact could be the greatest of the bunch. Yet as exciting as the potential of this farm system may be, the hope for Hoyer and his front office is that the major-league club will draw much more attention in 2023 and beyond.

(Photo of Willson Contreras: David Banks / USA Today)