The Chicago Cubs are reportedly considering Japanese ace Tatsuya Imai and Padres righty Michael King as potential free agent signings. Both pitchers offer significant upside but come with notable risks. Imai's transition to MLB and King's injury history are concerns. The Cubs' financial prudence and preference for signings with a reasonable floor may influence their decision. The team's recent signings, like Shota Imanaga, have been structured to protect against financial mistakes. The Cubs are weighing the potential upside and risks of Imai and King, with internal calculations about their value and likelihood of success. The latest reports mention King's potential signing with the Yankees, Red Sox, Orioles, and Mets, while Imai's posting fee and potential price tag of $150-200 million are under scrutiny. The Cubs' willingness to commit such a large sum to a relative unknown is questionable. The posting expiration for Imai on January 2nd adds urgency, with potential ripple effects on other deals. The outcome of these negotiations will depend on the actions of free agents, pursuing teams, and trade partners, with a potential deadline approaching.