15 most expensive contracts in MLB history and how they turned out

4. MLB contracts: Manny Machado, SDP – $350M/11 years

After loading up at the trade deadline last season, the San Diego Padres continued building themselves into one of the strongest contenders and biggest spenders this offseason by extending Manny Machado with one of the most expensive MLB contracts ever.

The mammoth 11-year, $350M extension kicks in this year and will finish after the 2033 season when the third baseman will be 41.

After confirmation that Machado was planning to opt out of his current 10-year deal following the season, the Padres secured his services for the remainder of his career.

The former third-overall pick has been invaluable for the Padres on the hot corner over the last few seasons. He helped the team reach the playoffs in 2022 and get all the way to the NLCS before losing out to the upstart Phillies.

Not to mention the two All-Star appearances he’s had while in a Padres uniform, plus a Silver Slugger and finishing top-three in MVP voting in 2020 and 2022.

While Machado turns 31 this season and eventual decline is inevitable, the Padres are banking on a few more elite-level years out of him. The decision to replace his previous contract was made easier after he had what could be considered close to a career year last season, in which he batted .298/.366/.531 with 100 runs, 102 RBI, 32 home runs and a 7.4 fWAR.

Machado also made a case for himself with his performance in last year’s playoffs. In 12 games, he slashed .271/.327/.583 with four home runs, four runs scored, and seven batted in.