The Chicago Cubs are on track to return to the postseason for the first time since 2020. Cubs manager Craig Counsell is still ironing out the weaknesses on his team with a playoff series looming. With stars like Kyle Tucker and Pete Crow-Armstrong leading the way, Chicago is a dangerous team in the National League. However, a lot is riding on the postseason for Tucker.

The veteran outfielder joined the Cubs in arguably the biggest move of the 2024 offseason. Tucker walked in the door and changed the energy around Chicago's clubhouse. Despite struggling in 2024, the team bounced back in a big way thanks to their new outfielder and the emergence of Crow-Armstrong. Both made it to the All-Star Game and started for the National League.

One other thing that both All-Stars have in common is their contract situations. Both Tucker and Crow-Armstrong have been in stalemates with the Cubs when it comes to their deals. While the latter is the more important piece for Chicago to keep around long-term, the team would like to keep both of them. However, the front office might have to make tough decisions this winter.

If the Cubs do not come to an agreement with Tucker, he will be an unrestricted free agent in the offseason. He will be the clear top player on the market if Chicago allows things to get to that point. However, it looks like Counsell and the organization might be waiting to see what happens in the postseason. The team's performance could play a big role in the outcome of the stalemate.

Tucker has said throughout the year that he likes playing with the Cubs. If the team reaches what he wants in his next contract, he would likely sign and play with Crow-Armstrong for years to come.

Tucker's weak second half is giving the Cubs pause

Chicago Cubs right fielder Kyle Tucker (30) hits a double to drive in two runs in the sixth inning against the Milwaukee Brewers at American Family Field.
Benny Sieu-Imagn Images

Tucker was one of the best players in all of baseball in the first half of the regular season. He and Crow-Armstrong were early NL MVP candidates before Los Angeles Dodgers superstar Shohei Ohtani started to run away from the pack. However, the outfielder's production has been down since the All-Star break, a concerning development that Counsell has had to deal with.

Some of Tucker's shortcomings might be because of his calf injury, but the team has struggled to string together wins. Chicago appears to be comfortably in the playoffs as an NL Wild Card team. However, there are legitimate concerns in the team's offense when it comes to producing against truly elite pitching. Tucker's performance at the plate will play a huge role in fixing that.

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Taking his entire season into perspective, the All-Star might is having one of the best years of his career. Slashing .270/.381/.472 with an OPS of .854 has Tucker at the top of the list when it comes to the Cubs' contributors. Despite his success, fans in Chicago want more from him heading into the playoffs. They hope he can return from the injured list and get back into a rhythm.

Tucker's shortcomings in the second half give the Cubs' front office a good reason to without a big deal. If he can't break out of his slump, he might not be worth the payday he is looking for. At that point, Chicago might as well save its money and pursue a young star this offseason, like Steven Kwan. The Cubs are playing a dangerous game, and could pay for it by getting neither of them.

If the Cubs don't pay Tucker now, someone will outbid them

Chicago Cubs right fielder Kyle Tucker (30) bats against the Los Angeles Dodgers during the ninth inning during the Tokyo Series at Tokyo Dome.
Darren Yamashita-Imagn Images

Tucker went to the Cubs because the Houston Astros traded him there. He did not have control over where he went, which is part of the reason why Chicago pursued him. The organization hoped that Counsell could help convince him to stay with the team and be its face for the rest of his career. The Cubs' manager has given his star a lot of attention and assistance throughout the year.

Tucker is sold on Chicago, but it may not be mutual. However, the Cubs' patience is a double-edged sword. They were not the only team in the race for Tucker during the offseason, but had the best package to trade. In free agency, it does not matter how many talented young prospects Chicago has. Teams like the Mets and Dodgers can easily offer larger deals than a smaller market team.

A lot of the Cubs' season is riding on what happens in the fall. Crow-Armstrong stands among franchise legends in the record books, but lacks any serious playoff experience. Chicago will lean on Tucker heading into the postseason, hoping that he can break out and lead a deep run. If he does, the Cubs are more likely to keep him around. If not, things will get interesting.