4. Trevor Bauer - three years, $103 million, 2021
The self-proclaimed inventor of short-term, high AAV deals, Trevor Bauer parlayed his fraudulent 2020 Cy Young campaign into a $100 million contract, and for some reason Friedman and the Dodgers took the bait. Bauer pitched in 17 games before sexual assault allegations derailed his MLB career. The Dodgers will pay him $22.5 million to not pitch for them in 2023.
3. Kevin Brown - seven years, $105 million, 1998
Major League Baseball's first $100 million contract. WOW! Brown came over from his lone year with the Padres (he finished third in the Cy Young voting) and landed a seven-year deal, but only lasted five in LA (he was lated traded to the Yankees). Brown, from his age-34-38 seasons with the Dodgers, went 58-32 with a 2.83 ERA, 3.16 FIP and 1.10 WHIP in 137 games (129 starts). He missed a good chunk of time in 2001-2002 with injuries, but racked up over 20 WAR in his five years. Worth it.
2. Zack Greinke - six years, $147 million, 2012
Greinke never finished this contract because he opted out, but how exciting was LA when he was atop the rotation with Kershaw? The Dodgers made the right call signing him away from the Angels (who tried to keep him after acquiring him at the 2012 trade deadline) and Greinke rewarded LA with a 51-15 record, 2.30 ERA, 2.97 FIP and 1.03 WHIP in 92 starts. He was also very good in the postseason, despite the team falling short from 2013-2015. The Dodgers do this again every time.