Who will be MLB’s next $500 million player? After Vlad Guerrero Jr., predicting the next huge contract

Vladimir Guerrero Jr. and the Toronto Blue Jays recently agreed to terms on what’s now the third-largest contract in Major League Baseball history. The two sides forged a 14-year, $500 million extension early in what would’ve been Guerrero’s walk year, likely keeping the homegrown star in for Toronto for the rest of his career. That brings us to this updated list of the most lucrative contracts ever in MLB: 

• Juan Soto, Mets: $765 million (15 years)
• Shohei Ohtani, Dodgers: $700 million (10 years)
• Vladimir Guerrero Jr., Blue Jays: $500 million (14 years)
• Mike Trout, Angels: $426.5 million (12 years)
• Mookie Betts, Dodgers: $365 million (12 years)

The logical next question is the matter of which players might be in line to be the next $500 million in MLB. Obviously, it’s a vanishingly rare contractual feat given that just three players have crossed that once-imponderable threshold. On the other hand, which is wearing multiple diamond rings and a Rolex, these three contracts of note have come about in a span of less than a year and a half. In other words, the market for premium baseball talent has spoken, and it’s saying that $500 million is what the best players cost on the open market or with open-market levels of leverage. 

Relative youth and surpassing excellence are generally what leads to massive contracts, so with those principles in mind let’s have a look at five names who have at least an outside shot at getting to half billion crisp dollar bills, either by eventual free agency or via long-term extension that buys out several of those free-agent years. Obviously, Bobby Witt Jr. of the Kansas City Royals would be prominent in this discussion under normal circumstances, but he’s already signed an extension that could see him locked up through age 37 depending upon how the array of player and club options play out. 

As for those who do have a shot, here they are in order of estimated likelihood …

1. Gunnar Henderson, SS, Orioles

Free agency date: After the 2028 season

Henderson is a plus-fielding shortstop who across parts of four big-league seasons has a slash line of .266/.344/.500, and for his career he’s averaged 32 home runs per 162 games played. With a WAR of 9.1 last season, he clearly has MVP capabilities. He arrived in the majors at age 21, which puts Henderson in line for free agency well before he reaches 30. That’s precisely the kind of player who gets paid big money in MLB. 

2. Elly De La Cruz, SS, Reds

Free agency date: After the 2029 season

One of the most electric players in baseball, De La Cruz combines pop at the plate, with best-in-class baserunning, and he also mans the premium position of shortstop. Elly’s star power is unmatched among the younger set in baseball, which only adds to his market appeal. Like Henderson, De La Cruz also started his MLB service-time clock running at age 21. 

3. Kyle Tucker, OF, Cubs

Free agency date: After the 2025 season

The 28-year-old Tucker is one of the more complete players around right now. For his career, he owns an especially strong OPS+ of 141, and he’s a plus glove in right field. Tucker also runs the bases well, and his power-plus-contact skill combo at the plate suggests he’ll age well as a hitter. He’s off to a thumping good start in this, his walk year. Will Tucker make it three straight winters in which a contract worth $500 million (or much more in the case of Ohtani and Soto) is handed out? He has a real shot. 

4. Paul Skenes, RHP, Pirates

Free agency date: After the 2029 season

It seems wild to ponder a pitcher fetching this kind of figure, but Skenes is the rare tandem of elite skills and results plus star appeal. As well, it’s hard to imagine that Bob Nutting, one of the truly useless owners in MLB today (competitive category, that) ponies up for any kind of extension. As such, that’s plenty of time for salary inflation to do its work before Skenes reaches free agency coming out of his age-27 season. Provided he stays generally healthy, he may hit the market with multiple Cy Young awards. 

5. Jackson Holliday, 2B, Orioles

Free agency date: After the 2030 season

The former top overall pick of the 2022 draft hit the majors for the first time as a 20-year-old, and now he’s a fixture in the loaded Baltimore infield. He’s showing signs in the early going this season of reaching his expected level. If he does and then sustains it, then Holliday will be one of the best players in baseball. As the son of former All-Star Matt Holliday, there’s no “economic desperation” that sometimes leads players to quite understandably sign below-market extensions. This one’s more speculative the names above, perhaps, but Holliday profiles as a star middle infielder who’ll hit the market at a young age as free agents go.