The Twins' pursuit of Willingham was linked to Cuddyer, as the club prioritized a deal with Cuddyer but opted to go with Willingham as a cheaper alternative at $21 million over three years.
Minnesota offered Cuddyer a three-year deal reportedly worth $24 million during the Winter Meetings, but Cuddyer decided to leave for a bigger offer.
The decision to sign Willingham also means the Twins are likely moving on from free-agent outfielder Jason Kubel.
"There's no secret that we're trying to retain players here, but we got to the point of no return," general manager Terry Ryan said of the negotiations with Cuddyer. "We didn't want to be left without, and consequently this is the situation that we felt was best at the time and we feel like it's going to be a good fit for the next three years."
It was a delicate situation for the Twins and Willingham's agent, Matt Sosnick, as all of the parties involved knew the Twins were waiting on Cuddyer to make a decision. But the Twins ultimately decided to go with Willingham, and they are expected to use the money they saved on improving their pitching staff.
"It was tough for us because we knew Terry had a loyalty to Michael," Sosnick said. "He was going to give Michael every chance to come back and that's what they did. They set themselves up as a family and are very loyal to their own."
The Twins have also set themselves up for a potential Draft windfall. Minnesota is already set to receive two compensatory picks because Cuddyer was a modified Type A free agent: a sandwich pick between the first and second rounds, plus the choice immediately preceding the Rockies' pick in the second round, because Colorado's first-rounder -- No. 10 overall -- is protected. If Kubel, a Type B free agent, signs with another team, the Twins will receive another sandwich pick. Moreover, Minnesota will not lose a pick for signing Willingham, who, like Cuddyer, was a modified Type A free agent.
Willingham and Cuddyer, who are both 32, profile as similar players offensively, while Cuddyer adds a bit more versatility defensively because of his ability to play first base.
Willingham has a career line of 262/.361/.475 (batting average/on-base percentage/slugging percentage) while Cuddyer is a career .272/.343/.451 hitter. So while Willingham doesn't hit for as high of an average as Cuddyer, he makes up for it with his ability to get on base and his power.
Willingham, who hit .246/.332/.477 with a career-high 29 homers and 98 RBIs in 136 games with the A's last year, said he never looked at himself as Cuddyer's replacement when signing his new deal.
"I can't say that I've thought about that," Willingham said. "I know and respect Michael Cuddyer as a competitor and playing against him. And I know his whole career has been with the Twins but it wasn't something I thought about."
So after parts of 11 seasons with the Twins, Cuddyer is moving on and the Twins are readying themselves for a new era that involves Willingham in right field. But Cuddyer, who was known for his clubhouse presence and leadership, will be missed by the Twins.
"He's actually the last player left on the roster from when I took over as manager in '02," Twins manager Ron Gardenhire said. "So we have a great relationship. He's a great player. These guys put a lot of work in and have a right to free agency and test the waters."