5 Players Who Should Get Extensions

These 5 young players should be locked up immediately.

There are a handful of superstar players or players who have superstar potential that teams should wait no longer and lock up as part of the organization’s future core. All five of the players below are pre-arbitration eligible currently meaning the team could potentially get a team friendly deal as they buy out the the remaining years of arbitration. These are the types of players that should be with these organizations for their entire careers.

Gunnar Henderson: 24 years-old

Free Agent: 2029

It’s surprising that the Orioles haven’t locked up their star shortstop yet. After winning the Rookie of the Year in 2023 and finishing 4th in the MVP last season with a 9.1 WAR campaign, what more does Henderson have to do to show them that he is worthy of being their franchise player? Oh, and he did all of that in his age 22 and 23 seasons. After new owner David Rubenstein told fans that this would be a new age of Orioles baseball, he has done nothing to truly invest in winning.

Extending Henderson would be a great sign to the fan base that they are serious about winning. It’s in the Orioles best interest to get a deal done immediately because Henderson will be entering his first year of arbitration after this season. After each season that the Orioles wait, the price tag will only go up. And there is the possibility that if they wait too long, Henderson will decide to bet on himself and wait until he can test the free agent waters.

If the Orioles are interested in extending Henderson before he hits arbitration, the deal to look at is what the Kansas City Royals gave Bobby Witt Jr. The Royals gave Witt Jr. an extension prior to the start of the 2024 season. Witt Jr. got a 7 / $148M deal with team / player options for 2031 - 2037. The extension showed a lot of creativity by the Kansas City front office as the deal could reach up to $288.7M. Gunnar Henderson only has an additional half season of service time than Bobby Witt Jr. did at the time he signed his extension. There is no reason the Orioles do not commit to their superstar shortstop and make a serious commitment to the future of the organization.

Elly De La Cruz: 23 years-old

Free Agent: 2030

The Cincinnati Reds superstar is on a path that is very similar to the path Bobby Witt Jr. was on back in 2023, the season before he got his big deal. This year is only Elly De La Cruz’s second full season in the big leagues. De La Cruz unfortunately lost his rookie status in 2023 but last season in his first full big league season Elly finished 8th in the MVP voting as he put together a 5.2 WAR season. De La Cruz flashes his five tools on a daily basis as he might be the most exciting player in baseball with his power, speed, and rocket for an arm. The fact that Elly is a 6’5” shortstop also makes him such a fascinating player to follow. The talent and the potential for De La Cruz is off the charts as he projected to beat most of last year’s numbers through the first half of this season.

The unfortunate truth is that Reds owner Bob Castellini is a a cheap owner as the Reds are consistently in the bottom third of the league in payroll. The Reds fans haven’t had a player to commit to since Joey Votto left town. This is a great opportunity for the Reds front office to show that they are committed to building a winning team.

Elly De la Cruz will be in the exact same situation that Bobby Witt found himself in this winter. De La Cruz will have four years of team control remaining. I think a similar deal to Witt Jr’s 7/$148 with options is a deal the Reds should be willing to do. Like the Bobby Witt Jr. extension, it will take some creativity from the front office to get this done.

James Wood: 22 years-old

Free Agent: 2031

I’m not sure many thought the Washington Nationals would have won the Juan Soto trade when they sent him to San Diego. But the Nationals did an incredible job by acquiring a package of talented players headlined by James Wood. The 22 year-old is a budding superstar. In his first 162 games in the big leagues, Wood has hit 31 home runs, has 105 RBI, and has an .859 OPS. He’s currently putting together a 3.5 WAR season and should be an All-Star. The game isn’t supposed to be this easy for a player in his first full season.

Wood will not be a free agent until 2031 and he will not be arbitration eligible until after the 2027 season. For an organization that has lost superstar talents in the past like Bryce Harper, Trea Turner, and Juan Soto, it’s time for the Nationals to finally commit. They don’t have to wait until Wood is two years away from testing the free agent waters. Get it done now. What more does Wood have to show to get a deal? Wood is the type of player that team’s would dream to build around. The whole reason you trade a player of the caliber of Juan Soto is that you get another star in return. And they did just that.

The comp for an extension this early is Julio Rodriguez. After one year, Rodriguez signed a 7/$119 with five player options. J-Rod’s potential max if he opts into all of his options and reaches the incentives is $470M. There was a lot of creativity in the Rodriguez deal but giving players incentivized contracts may become the new norm if you want to sign players to lifetime deals. This is a deal that needs to happen before the start of 2026.

Pete Crow-Armstrong: 23 years-old

Free Agent: 2031

We know that the Cubs were interested in an extension with Pete Crow-Armstrong. Earlier this year they talked about an extension worth around $75M but PCA turned it down. And it’s a good thing he did. PCA has been the breakout player this year with a wRC+ of 129 with 21 home runs and playing Gold Glove defense in center field. PCA is currently 7th in all of baseball with a 3.9 fWAR. Right now, Crow-Armstrong would receive MVP votes for his performance.

The comp that I have in mind for PCA is Jackson Merrill. The Padres young star had a massive rookie season finishing second in the ROY and 9th in the MVP voting and signed a 10 / $156M deal before the season. PCA is arbitration eligible after the 2027 season. If the Cubs wait until after the season, PCA will have one less year of pre-arbitration than Merrill did, which would likely mean that PCA would get a little more money because the Cubs would be buying out only one year of pre-arbitration.

The Cubs have some interesting decisions to make in the near future. They have to decide if they are willing to go all-in on Kyle Tucker. I imagine a Tucker deal will be in the $400M range. Extending PCA should be another one of those important decisions.

Roman Anthony: 21 years-old

Free Agent: 2032

This one might surprise you because Anthony debuted only three weeks ago but the Red Sox organization is a bit of a mess right now. The shocking Devers trade has put a ton of uncertainty in Boston. Locking up Roman Anthony would be a sign that their is a direction. With the Red Sox playing Anthony and Marcelo Mayer almost every day, they are signaling that the kids are not just the keys to the future but also the present. By calling Anthony up as a 21 year-old, they showed that they believe he has the talent to be successful. Nothing in the minors suggested he won’t be successful.

So far in 62 ABs, Anthony has a fairly low batting average however he hitting the ball extremely hard. The ABs are quality and and he looks like he belongs. In terms of a comp for an extension, there have been players who have signed extensions with limited service time. One of the best comps is Corbin Carrol. The Diamondbacks signed Carrol to an 8 / $111M deal with a club option that could run the deal to $134M. The other comp to look at is Jackson Merrill, who signed after his rookie season (10 / $156). Anthony has talked with the media about an extension when asked and said that it would have to make sense for him to do the deal. Even if the Red Sox have to slightly overpay to get a deal done, they should get it done. They have a ton of payroll flexibility and signing him to a 10+ year deal would be a huge building block for this organization moving forward.

Saving Money

Extending all five of those players would save their respective organizations a lot of money moving forward. With contracts, players are always trying to top the previous biggest deal. I’m not sure anyone will come close to Juan Soto’s record breaking deal ($765M) but when multiple teams are bidding, you never know what number is going to get the job done. The longer these teams wait, the bigger the price could become.

Which players would you give a big extension to?