While the Cubs were busy Tuesday deciding on which prospects to protect from the Rule 5 Draft next month, a beloved Cub officially made the decision on his own future with the organization. Prior to the deadlines for teams to add Rule-5 eligible prospects to their 40-man rosters and for players to make decisions on qualifying offers, Willson Contreras rejected the one-year, $19.65 million qualifying offer extended by the Cubs last week.

It wasn’t an unexpected outcome; president of baseball operations Jed Hoyer made it clear at his end-of-season press conference that the Cubs would be making the offer, but the expectation has been that Contreras is seeking long-term security in a place that appreciates what he brings to the table.

“For me, it’s more like feeling that I’m wanted,” Contreras said during the Cubs’ last homestand of the year. “I want to be somewhere that I’m wanted and I feel like they’re going to appreciate what I do on the field and off the field. A place that appreciates what I bring to the clubhouse and what I can do.”

It’s another signal of the end of an era for the Cubs. It’s somewhat jarring to realize that, of all the players from the 2016 World Series title team (many of whom had only debuted in the previous few seasons), only Kyle Hendricks remains with the Cubs after Contreras rejected the qualifying offer and Jason Heyward was released Monday.

Tuesday’s intersection of deadlines, then, served as another checkpoint in the closing of the last chapter of Cubs baseball. However, it also helped display where the club is heading at this point in their rebuild.

With Contreras officially off the books, the front office’s task became filling out some of the spots remaining on 40-man roster before the protection deadline passed (entering Tuesday, seven roster spots were open). The Cubs took care of one of those by trading pitching prospect Alfredo Zarraga to the Rays in exchange for utilityman Miles Mastrobuoni, who will be in his age-27 season in 2023 after only just making his big league debut in September.

But of course, that wouldn’t be the last of the Cubs’ moves for the day. A number of players in the system would’ve been eligible to be selected in the Rule 5 Draft if they weren’t added to the 40-man roster by 5 p.m. Tuesday, but the Cubs selected the contracts of just four minor leaguers: Brennen Davis (No. 2 Cubs prospect, No. 48 overall), Kevin Alcantara (No. 3 Cubs, No. 86 overall), Ben Brown (No. 7 Cubs) and Ryan Jensen (No. 28 Cubs).

Davis, Alcantara and Brown had long been considered locks to be protected from the Rule 5 Draft, while Jensen’s case wasn’t as strong but certainly was worthy of consideration. If you’re curious, here’s part of why these four found their way onto the 40-man roster:

• Davis: He likely would’ve already made his big league debut at some point in 2022 had it not been for a back injury that required surgery and kept him out of action for over three months. He would likely be in line for Opening Day had more health issues not limited him to just five games in the Arizona Fall League. Regardless, there’s a reason he entered the season as the Cubs’ No. 1 prospect. He has one of the best bats in the system when he’s right (as evidenced by the fact he never posted a wRC+ below 132 at any level from 2018 through ’21), and he’s got the defensive chops to capably play each outfield position. Whether or not he makes his debut at all in 2023 after a lost season in 2022, adding Davis to the 40-man was a no-brainer.
• Alcantara: Considering the Cubs got Alcantara from the Yankees as part of the return for Anthony Rizzo, and adding in the fact that he’s made his way onto various top-100 lists, he was all but certain to make the 40-man roster this offseason. He’s only played one full season of pro ball and hasn’t even played above Low-A, but some evaluators say he may have the highest upside of anyone in the organization. No way were the Cubs going to let a player like that get away this winter.
• Brown: Acquired at the trade deadline for David Robertson, Brown had probably already done enough in the Phillies’ system to show the Cubs he was worthy of a spot on the 40-man roster. All he did after joining Double-A Tennessee was post a 32.1 percent strikeout rate and 9.5 percent walk rate over seven appearances. Seen as a starting pitching prospect, Brown’s fastball tops out at around 98 mph (much faster than most of the starters on the Cubs’ current roster), and his still-developing breaking pitches are impressive in their own right. If things go well, Brown may find his way onto the big league roster sometime next season, so this was another player the Cubs couldn’t let get away.
• Jensen: It seems a month-long stint on the developmental list did wonders for the Cubs’ first-round pick back in 2019. He struggled with his command early on, and those issues weren’t completely solved by the time he went back to Tennessee, but some improvement in controlling what is already an exciting repertoire gave the Cubs enough of a reason to make sure he wasn’t poached by another team this winter. He’s exclusively started games in the minors, but the Cubs’ ideal 2023 rotation likely doesn’t include Jensen. Still, there’s certainly a chance that he may get the call for a bullpen role later in the season.

There are plenty of other names that the Cubs would’ve liked to protect if they could, but the fact is that most of them won’t be selected in the Rule 5 Draft. Having to roster a player for the entire season (without being able to option them down) can be enough to sway teams away from taking some of these players the Cubs didn’t protect but still think highly of. Add in the fact that these four players now bring the total to 38 players on the Cubs’ 40-man roster, and it’s pretty clear that the Cubs wanted the added flexibility of having those two empty spots.

Regardless, Tuesday marked another turning point in the Cubs’ rebuild. You can’t completely rule out a Contreras return until he signs elsewhere, but him rejecting the qualifying offer signaled an end to his time in Chicago. And in his place, the Cubs helped some of who they hope will be contributors to “The Next Great Cubs Team” take the next step in their journeys to the big leagues.

As much as Contreras was a part of winning teams on the North Side of Chicago, it appears to be at the point where both sides are ready to move on. Contreras wants to get a deal he feels he’s worth, and the Cubs are setting the wheels in motion for this next era of winning Cubs baseball to begin.