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.
This news was originally published on this post .
About the author
2025 NFL Draft: Patriots’ Mr. Irrelevant pick is DB Kobee Minor, who played at Texas Tech, Indiana and Memphis
Mr. Irrelevant really was fairly irrelevant this year.The Patriots selected Kobee Minor, a defensive back who played at Texas Tech, Indiana and Memphis. The NFL Network desk seemed caught off guard by the pick. Analyst Daniel Jeremiah admitted during the NFL Network broadcast that he hadn't watched Minor, and the pick was a flier. Minor had just 38 tackles and no interceptions, but two sacks, in his final college season with Memphis. Before his last season, he had started just nine games in his college career.AdvertisementAdvertisementAdvertisementThe final pick was originally held by the Kansas City Chiefs, but they traded it to the Patriots. The Chiefs got the 228th overall pick for Nos. 251 and 257, which was the last pick of the draft. The family of Mr. Irrelevant founder Paul Salata announced the pick as a way to celebrate the […]
Barcelona beats Real Madrid in extra time to win Copa del Rey
Barcelona beat Real Madrid 3-2 in extra time to claim a record-extending 32nd Copa del Rey title on Saturday and launch its bid for a treble.Pedri González scored from long range to give Barcelona the lead in the 28th minute at La Cartuja Stadium.Kylian Mbappé came off the bench at halftime and scored from a free kick for Real Madrid in the 70th. Midfielder Aurélien Tchouaméni headed Madrid in front in the 77th.But Ferran Torres leveled in the 84th and forced extra time.Jules Koundé then pounced on a pass by Brahim Díaz and slotted a shot into the low corner of Thibaut Courtois' net for the 116th-minute winner.Barcelona will carry this momentum into Wednesday's start of its Champions League semifinal against Inter Milan. It also leads La Liga by four points over Madrid.Barcelona has beaten Madrid in all three of […]
2025 NFL Draft: Ohio State falls 1 pick shy of modern era record for single draft despite hitting 14 with 72 selections left
Ohio State tied for the second-most players selected in a single NFL Draft with 14 this year.The national champions started with wide receiver Emeka Egbuka picked by the Tampa Bay Buccaneers at No. 19 overall Thursday, and quarterback Will Howard became pick No. 14 at 185th overall. That left 72 picks for the Buckeyes to tie Georgia's 2022 record of 15, but no more of them were selected.AdvertisementAdvertisementAdvertisementGeorgia broke the record in the sixth round in 2022 when John FitzPatrick became the 15th Georgia player taken when he was chosen with the 213th pick. Forty-nine picks remained after that with no more Bulldogs being selected.Ohio State also had 14 players selected in 2004, while LSU had 14 players drafted in 2020.The Buckeyes didn’t have a player selected in the top 15, but then Ohio State went on a run. Offensive […]
2025 NFL Draft: Ohio State has 14 players taken, leads all schools in first-rounders
<!--> Ohio State made college football history this year when it became the first team to win a national championship in the new 12-team playoff era. The Buckeyes followed that up with 14 players being selected in the 2025 NFL Draft.Ohio State came within one of tying the all-time record set by Georgia in 2022 for the most players taken in a single draft (15). Like Ohio State, Georgia was also coming off a national championship win that season. The Buckeyes led all schools this year with four first-round picks, followed by Georgia, Michigan and Texas (three each). Ohio State has produced more first-rounders than any other college since the NFL Draft began in 1936.ADVERTISEMENT -->Here's every Ohio State player who was selected in the 2025 NFL Draft:The two draft-eligible Buckeyes who weren't selected were C Seth McLaughlin and OT Josh […]
Eagles 2025 NFL Draft takeaways: Philadelphia gets large draft class, stockpiles future picks
PHILADELPHIA — The Philadelphia Eagles finished the 2025 NFL Draft with 10 selections. As reigning Super Bowl champions, they operated from the back end of the rounds. The positioning forced the Eagles’ war room to be more strategic. At one time, aggressive. More often, conservative. General manager Howie Roseman executed five draft-day trades in a series of moves that yielded one of the largest draft classes of his tenure. He also acquired a fifth-round selection for a 2026 arsenal of picks that now has a total of 12.AdvertisementRoseman, his personnel department and the Eagles coaching staff will now start chasing down undrafted free agents to sign. Philadelphia’s offseason roster will continue to take shape as the Eagles prepare for voluntary OTAs, which begin May 27. Here’s a breakdown of the key takeaways for the Eagles from the draft.Best value pickThe […]
How much money did Quinn Ewers lose by not returning for NIL in college football, sliding in 2025 NFL Draft?
USATSI After a long wait, Quinn Ewers was drafted at pick No. 231 by the Miami Dolphins in the seventh round of the 2025 NFL Draft. It was clear that with heir apparent Arch Manning waiting in the wings, he'd have to play somewhere else in 2025. Ewers entered this draft class with concerns over his arm strength and some worries about a nagging injury that hampered him in the 2024 season for Texas.Throughout the NIL era, there's an interesting theme running through Day 3 of every NFL Draft, and that's whether a player could have earned more by staying in school. There are myriad reasons why a player goes to the draft beyond money, but it is something to factor into any player's decision. Some players who are borderline draftable opt to return to school to at least get […]
Related
2025 NFL Draft: Patriots’ Mr. Irrelevant pick is DB Kobee Minor, who played at Texas Tech, Indiana and Memphis
Mr. Irrelevant really was fairly irrelevant this year.The Patriots selected Kobee Minor, a defensive back who played at Texas Tech, Indiana and Memphis. The NFL Network desk seemed caught off guard by the pick. Analyst Daniel Jeremiah admitted during the NFL Network broadcast that he hadn't watched Minor, and the pick was a flier. Minor had just 38 tackles and no interceptions, but two sacks, in his final college season with Memphis. Before his last season, he had started just nine games in his college career.AdvertisementAdvertisementAdvertisementThe final pick was originally held by the Kansas City Chiefs, but they traded it to the Patriots. The Chiefs got the 228th overall pick for Nos. 251 and 257, which was the last pick of the draft. The family of Mr. Irrelevant founder Paul Salata announced the pick as a way to celebrate the […]
Barcelona beats Real Madrid in extra time to win Copa del Rey
Barcelona beat Real Madrid 3-2 in extra time to claim a record-extending 32nd Copa del Rey title on Saturday and launch its bid for a treble.Pedri González scored from long range to give Barcelona the lead in the 28th minute at La Cartuja Stadium.Kylian Mbappé came off the bench at halftime and scored from a free kick for Real Madrid in the 70th. Midfielder Aurélien Tchouaméni headed Madrid in front in the 77th.But Ferran Torres leveled in the 84th and forced extra time.Jules Koundé then pounced on a pass by Brahim Díaz and slotted a shot into the low corner of Thibaut Courtois' net for the 116th-minute winner.Barcelona will carry this momentum into Wednesday's start of its Champions League semifinal against Inter Milan. It also leads La Liga by four points over Madrid.Barcelona has beaten Madrid in all three of […]
2025 NFL Draft: Ohio State falls 1 pick shy of modern era record for single draft despite hitting 14 with 72 selections left
Ohio State tied for the second-most players selected in a single NFL Draft with 14 this year.The national champions started with wide receiver Emeka Egbuka picked by the Tampa Bay Buccaneers at No. 19 overall Thursday, and quarterback Will Howard became pick No. 14 at 185th overall. That left 72 picks for the Buckeyes to tie Georgia's 2022 record of 15, but no more of them were selected.AdvertisementAdvertisementAdvertisementGeorgia broke the record in the sixth round in 2022 when John FitzPatrick became the 15th Georgia player taken when he was chosen with the 213th pick. Forty-nine picks remained after that with no more Bulldogs being selected.Ohio State also had 14 players selected in 2004, while LSU had 14 players drafted in 2020.The Buckeyes didn’t have a player selected in the top 15, but then Ohio State went on a run. Offensive […]
2025 NFL Draft: Ohio State has 14 players taken, leads all schools in first-rounders
<!--> Ohio State made college football history this year when it became the first team to win a national championship in the new 12-team playoff era. The Buckeyes followed that up with 14 players being selected in the 2025 NFL Draft.Ohio State came within one of tying the all-time record set by Georgia in 2022 for the most players taken in a single draft (15). Like Ohio State, Georgia was also coming off a national championship win that season. The Buckeyes led all schools this year with four first-round picks, followed by Georgia, Michigan and Texas (three each). Ohio State has produced more first-rounders than any other college since the NFL Draft began in 1936.ADVERTISEMENT -->Here's every Ohio State player who was selected in the 2025 NFL Draft:The two draft-eligible Buckeyes who weren't selected were C Seth McLaughlin and OT Josh […]
Eagles 2025 NFL Draft takeaways: Philadelphia gets large draft class, stockpiles future picks
PHILADELPHIA — The Philadelphia Eagles finished the 2025 NFL Draft with 10 selections. As reigning Super Bowl champions, they operated from the back end of the rounds. The positioning forced the Eagles’ war room to be more strategic. At one time, aggressive. More often, conservative. General manager Howie Roseman executed five draft-day trades in a series of moves that yielded one of the largest draft classes of his tenure. He also acquired a fifth-round selection for a 2026 arsenal of picks that now has a total of 12.AdvertisementRoseman, his personnel department and the Eagles coaching staff will now start chasing down undrafted free agents to sign. Philadelphia’s offseason roster will continue to take shape as the Eagles prepare for voluntary OTAs, which begin May 27. Here’s a breakdown of the key takeaways for the Eagles from the draft.Best value pickThe […]
How much money did Quinn Ewers lose by not returning for NIL in college football, sliding in 2025 NFL Draft?
USATSI After a long wait, Quinn Ewers was drafted at pick No. 231 by the Miami Dolphins in the seventh round of the 2025 NFL Draft. It was clear that with heir apparent Arch Manning waiting in the wings, he'd have to play somewhere else in 2025. Ewers entered this draft class with concerns over his arm strength and some worries about a nagging injury that hampered him in the 2024 season for Texas.Throughout the NIL era, there's an interesting theme running through Day 3 of every NFL Draft, and that's whether a player could have earned more by staying in school. There are myriad reasons why a player goes to the draft beyond money, but it is something to factor into any player's decision. Some players who are borderline draftable opt to return to school to at least get […]
Be the first to leave a comment