Daisuke Matsuzaka
If this list was based on the amount of hype leading to their arrival, Daisuke Matsuzaka would be at the top. Dice-K Mania was in full force when the Red Sox signed the Japanese star pitcher in 2007.
The Red Sox first had win a blind auction which cost them a $51.1 million posting fee in order to gain exclusive rights to negotiate with the Japanese right-hander. Boston then inked Matsuzaka to a 6-year, $52 million deal.
Dice-K was a legend in Japan with a full arsenal of pitches at his disposal, including the mystifying “gyro-ball” that captivated the interest of fans who were eager to see him on the mound.
Expectations were unrealistically high for a pitcher who had never faced major league-level talent. Under the circumstances, Matsuzaka’s debut season was fairly solid. He won 15 games with a 4.40 ERA and finished fourth on the Rookie of the Year ballot.
Dice-K was also a key part of the Red Sox rotation when they won the World Series in his rookie year. He earned the win in the decisive Game 7 of the ALCS and in Game 3 of the World Series, logging at least five innings in each of those starts while limiting the opponent to only a pair of runs.
2008 was a breakout year for Matsuzaka. He was 18-3 with a 2.90 ERA to earn a fourth-place finish on the AL Cy Young ballot.
The heavy workload and high pitch counts he was known for in Japan eventually caught up with him and injuries spoiled the remainder of his career. Dice-K made no more than 12 starts and pitched fewer than 60 innings in three of his final four seasons in Boston. He owned a 5.53 ERA over that span, culminating in a brutal 8.28 ERA over 11 starts in 2012.
Matsuzaka spent two underwhelming seasons with the New York Mets before retiring after the 2014 season.
Overall, Matsuzaka’s tenure with the Red Sox was a disappointment amplified by the amount of hype that followed him here. His solid first two seasons and contributions to a championship get him on this list.