48. Kevin Brown

Kevin Brown's arrival in Los Angeles in 1999 marked a historic milestone as the first player in Major League Baseball to be awarded a contract exceeding $100 million. This extensive seven-year agreement, which transitioned him from San Diego to Chavez Ravine, was predicated on the expectation that he would be the pivotal element in securing a championship. Although the period known as the "Kevin Brown Era" is often viewed through the prism of the substantial financial investment and a series of injuries, the right-hander demonstrated a high level of efficiency that, when he was healthy, rendered him one of the most formidable sinkerball pitchers in franchise history.

Back in 1999, Brown hit a peak in his workload, pitching a season with 18 wins and over 250 innings, a true testament of his mastery in the National League. He demonstrated incredible control, striking out 221 batters and finishing sixth in the Cy Young voting. The following year, in 2000, he reached new heights of efficiency, capturing the ERA Title with an impressive 2.58 and leading the league in WHIP at 0.99. Throughout this exciting period, he was a key player, surpassing the 200-strikeout mark in consecutive years and proving once again that he was a formidable force in the game.

Brown faced a tough crossroads mid-contract. Between 2001-2002, injuries like chronic back, elbow, and shoulder problems led to a decline in durability. Once a key player, he only won 10 games in 2001 and just 3 in 2002, with a 4.81 ERA. During this period, focus shifted from his sinker to his salary, and fan expectations grew frustrated as the team missed the postseason.

In 2003, Brown had his final full season with the Blue, posting a 14-9 record with a 2.39 ERA. He was a key part of the rotation, earning his second All-Star selection and finishing in the top ten in ERA. However, that winter, the organization changed direction, and Brown was traded to the Yankees for Jeff Weaver and prospects.

Brown compiled a 58-32 record, a 2.83 ERA, and 784 strikeouts as a Dodger, which, while decent, earns him a spot here, will always be associated with a contract that his body couldn’t live up to.