The Chicago Cubs took a big risk last winter by trading for Kyle Tucker. The risk didn't pay off as the Cubs didn't go far in the postseason, and Tucker sits in free agency after the season.

The Cubs have never signed a free agent to a deal worth over $200 million, which doesn't bode well for their chances of re-signing him. Tucker is likely headed for a blockbuster contract.

Zach Mentz of Cleveland.com recently projected Tucker would sign a massive 11-year deal worth $440 million in free agency this winter. At that price, the Cubs will almost surely lose him.

"Tucker is the crown jewel of this year’s free agent class, and most predictions estimate he’ll break the $400 million mark," Mentz wrote. "His stats took a dip at Chicago’s Wrigley Field, which is often unfriendly to hitters du

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