Cubs' Kyle Tucker Needs Strong Finish To Secure Massive $400 Million Contract

Will Kyle Tucker of the Chicago Cubs receive a massive contract this winter?

Aug 24, 2025; Anaheim, California, USA; Chicago Cubs outfielder Kyle Tucker (30) walks against the Los Angeles Angels during the fifth inning at Angel Stadium. | Jonathan Hui-Imagn Images

After a strong stretch to end last week, the Chicago Cubs have slipped up a bit on their West Coast trip against the San Francisco Giants. 

The Cubs were building some momentum after winning a key series against the Milwaukee Brewers and then followed it up with a series sweep of the Los Angeles Angels. 

However, things have not gone well against the Giants with the offense underperforming and the pitching staff also being hit hard. Inconsistent play has been a bit of an issue for Chicago in the second half of the season, and just when it felt like they might have a chance to put some pressure on the Brewers with easy matchups coming up, they have had a letdown. 

Jonathan Hui-Imagn Images

Fortunately, one of their struggling stars has started to show some signs of turning it around, and that is important not only for the Cubs but for him as well. Getting this offense going again is going to be key for the team moving forward, and it starts with their star.

Thomas Harrigan of MLB recently wrote about Kyle Tucker needing to play well down the stretch to secure a $400 million deal in free agency. 

Will Tucker Receive the Massive Contract?

Jonathan Hui-Imagn Images

For quite some time, it felt like the star slugger of the Cubs was going to be a lock for a deal north of $400 million this coming winter. However, he went into a very significant slump, and reports later came out that he was playing through an injury. 

Fortunately, it does seem like he has snapped out of the slump a bit of late and might be getting healthy. Through August 27th, he has been able to get on a modest five-game hitting streak and, most importantly, has shown some signs of power during that stretch as well. 

After seeing his power disappear for a month, he has been able to hit three home runs during the hitting streak, including two against the Los Angeles Angels in the same game. 

Touch 'em all, King Tuck! pic.twitter.com/Z9qMcpXyeu

— Chicago Cubs (@Cubs) August 23, 2025

While the struggles for the extended stretch very well might have been injury-related, a $400 million investment is significant for a player who is now having a bit of a down year by his standards. 

With about a month to go and hopefully some playoff games as well, this will be an important stretch for Tucker. If he can get hot once again, it will put some of the concerns to rest, and he will have no problem securing the massive contract. 

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