Vladimir Guerrero Jr. and 10 Star Players MLB Teams Must Extend Before It's Too Late
It isn't just spring training that is fast approaching, as February and March also mark another special time for Major League Baseball.
It is extension season.
To make sure everyone is properly hyped, we're going to look closely at 10 candidates from around the league to receive contract extensions. And not just any candidates, mind you.
The teams in question ought to have a sense of urgency when it comes to signing these guys. Some are young building blocks who can only get more expensive. Others are established stars who are getting close to free agency, where aggressive buyers await.
Basically, teams should be worried about locking these guys up before the Los Angeles Dodgers can get their hooks in them.
We'll go one at a time, with those furthest from free agency at the beginning and those closest to it at the end. Each player's likelihood for an extension will be addressed with a "Probability Meter" that reads Low, Medium or High.
RHP Paul Skenes, Pittsburgh Pirates
1 of 10
Age: 22
2024 Stats: 23 GS, 133.0 IP, 94 H (10 HR), 170 K, 32 BB, 1.96 WRA
2025 Status: Pre-arbitration eligible, free agent after 2029
Why It Should Happen
The Pirates have been in a mood to do extensions of late, notably securing Ke'Bryan Hayes, Bryan Reynolds and Mitch Keller to deals that total 21 years and $253.5 million.
Good job, guys. Now do Paul Skenes.
That the Bucs should want to keep Skenes for the foreseeable future pretty much goes without saying. "Sensational" barely begins to describe his NL Rookie of the Year-winning 2024 season, in which he posted the lowest ERA by a live-ball era rookie starter.
Skenes otherwise has a level of celebrity that is extraordinarily rare for a Pirates player, and it isn't just because his pure stuff is straight out of Industrial Light & Magic. His charisma could be just as powerful a tool for creating new Bucs fans.
But Will It Happen?
"I haven't given it too much thought," Skenes said Sunday when asked about the possibility of an extension, according to Will Graves of the Associated Press.
Skenes, the No. 1 pick in the 2023 draft, may be on an island unto himself there. But when he does start thinking about it, he'll have every right to aim high. Perhaps as high as Yoshinobu Yamamoto's record deal for a pitcher at 13 years, $325 million.
It's hard to imagine such a deal being replicated by the Pirates. They have only ever done one nine-figure deal, and that one barely cleared the bar.
Probability Meter: Low
SS Elly De La Cruz, Cincinnati Reds
2 of 10
Age: 23
2024 Stats: 160 G, 696 PA, 25 HR, 67 SB, .259 AVG, .339 OBP, .471 SLG
2025 Status: Pre-arbitration eligible, free agent after 2029
Why It Should Happen
The Reds are another team that is notoriously stingy with its dollars, but they should want to make an exception for Elly De La Cruz.
Even as he took his lumps as a rookie in 2023, he was growing more comfortable in the box. It's little wonder that he made the leap to stardom in 2024, even if he did end up leading MLB with 218 strikeouts.
De La Cruz also led the league with 67 stolen bases, otherwise joining Bobby Witt Jr. and Jarren Duran in topping 30 doubles, 10 triples and 20 home runs.
Also, don't read too much into De La Cruz's league-leading 29 errors from last season. Per his 15 Outs Above Average, he was one of the best defenders in MLB even despite those.
But Will It Happen?
As they're both young, ultra-talented shortstops, it's fair to assume that De La Cruz noticed when Witt inked an 11-year, $288.7 million deal with the Kansas City Royals last year.
Could the Reds do a deal like that? In theory, yes. When adjusted for inflation, Witt's deal is close to the $225 million pact that the Reds made with Joey Votto in 2012. That deal is now long gone from their books.
But then there's the bad news: De La Cruz is repped by Scott Boras, whose general attitude toward extensions can be adequately described as "disdainful."
Probability Meter: Low
CF Jackson Merrill, San Diego Padres
3 of 10
Age: 21
2024 Stats: 156 G, 593 PA, 24 HR, 16 SB, .292 AVG, .326 OBP, .500 SLG
2025 Status: Pre-arbitration eligible, free agent after 2029
Why It Should Happen
If Jackson Merrill hadn't shared the race with Paul Skenes, he'd be the reigning NL Rookie of the Year.
As it is, Merrill was a deserving runner-up even though he didn't get going until the middle of May. Once he did, he was a .300 hitter with 22 home runs in 117 games.
Merrill's overall productivity was bolstered by a whole bunch of red on his Baseball Savant page. Of particular note is that he was in the 97th percentile for xBA and the 96th percentile for xSLG.
As Merrill also had 12 Outs Above Average in the field, he's primed for a long career as an increasingly rare sort of player: a two-way center fielder.
But Will It Happen?
According to Dennis Lin of The Athletic, the Padres did talk with Merrill about an extension last winter, when he was still awaiting his debut.
One wonders if San Diego felt motivated by the Milwaukee Brewers' eight-year, $82 million deal with Jackson Chourio. But even if that was the case, the boat for getting such a discount on Merrill has surely sailed.
Padres fans can feel optimistic knowing that, unlike the Pirates and Reds, their team has a history of big spending. But the writing is on the wall that such spending was never sustainable, and the biggest contracts on the Padres' books are going nowhere soon.
Probability Meter: Medium
RHP Logan Gilbert, Seattle Mariners
4 of 10
Age: 27
2024 Stats: 33 GS, 208.2 IP, 148 H (26 HR), 220 K, 37 BB, 3.23 ERA
2025 Status: Arbitration eligible, free agent after 2027
Why It Should Happen
When you're the best pitcher in arguably the best rotation in MLB, you must be pretty good.
Such is the case with Logan Gilbert, even if he is weirdly only No. 30 on the rWAR leaderboard for pitchers since 2021.
He's increased his innings every year he's been with the Mariners, culminating in a league-leading 208.2 in 2024. He also led MLB in WHIP at 0.887, which might come as a surprise given that he shared territory with not one, but two Triple Crown winners.
It'll be hard for Gilbert to push his workload any further, but it's remarkable that he's been as reliable as he has been. This is, after all, an era in which starters tend to work less, not more.
But Will It Happen?
Back in October, Adam Jude of the Seattle Times reported that there had been "little discussion about a long-term deal" between Gilbert and the Mariners.
Perhaps not coincidentally, the club's projected 2025 payroll is already at the same level where it ended 2024. Cash thus seems to be tight, which helps explain why the Mariners have been shopping Luis Castillo.
Even if the Mariners can't unload Castillo, however, it could be advantageous that his deal will end the same year as Gilbert's club control. An extension could effectively lock him into the same payroll niche that Castillo has occupied since 2023.
Probability Meter: Medium
SS Gunnar Henderson, Baltimore Orioles
5 of 10
Age: 23
2024 Stats: 159 G, 719 PA, 37 HR, 21 SB, .281 AVG, .364 OBP, .529 SLG
2025 Status: Pre-arbitration eligible, free agent after 2028
Why It Should Happen
What if I told you that Gunnar Henderson is on track to become one of the greatest shortstops of all time?
It's true. Though he didn't make his MLB debut until the final day of August 2022, Henderson is still fourth on the all-time rWAR leaderboard for shortstops through their first three seasons. Just below him are Bobby Witt Jr. and Francisco Lindor.
Henderson has a knack for producing loud contact, landing in the 95th percentile for hard-hit rate in 2023 and in the 97th percentile in 2024. Among shortstops, he and Witt occupy a tier unto themselves.
Defense is more of a gray area for Henderson, though he at least has Defensive Runs Saved on his side. He has 15 of those in three seasons.
But Will It Happen?
Like Elly De La Cruz, Henderson is another guy whose ears might have perked up when Witt signed his deal last spring.
For their part, the Orioles are interested in extending Henderson. It's certainly about time they extended someone, as owner David Rubenstein's $4.1 billion fortune has yet to be used for any long-term deals.
There's just one problem: Henderson is another Scott Boras client, and one who's notably closer to a free-agent payday than De La Cruz.
Probability Meter: Low
C Adley Rutschman, Baltimore Orioles
6 of 10
Age: 26
2024 Stats: 148 G, 638 PA, 19 HR, 1 SB, .250 AVG, .318 OBP, .391 SLG
2025 Status: Arbitration eligible, free agent after 2027
Why It Should Happen
How best to sum up Adley Rutschman's impact on the Orioles?
Ah, I know: Since his debut on May 11, 2022, the Orioles co-lead the American League in wins.
The caveat is that Rutschman's offensive returns have diminished, as he went from clearing a .800 OPS in 2022 and 2023 to a more meager .709 OPS in 2024. His defensive game is likewise not without warts, as he notably slipped as a framer last season.
Regardless, Rutschman is in the conversation for guys a team would want first if it could build the perfect roster. Impactful two-way catchers aren't exactly plentiful, much less ones as young and accustomed to winning as he is.
But Will It Happen?
Though he didn't single out Rutschman, Orioles general manager Mike Elias did say in 2023 that "part of the calculus of keeping this franchise healthy is pursuing or examining opportunities to possibly keep some of these guys longer."
Rutschman ought to be first in line after all he's done. He also figures to be more affordable than Gunnar Henderson, even if he and his reps shoot for Buster Posey's nine-year, $167 million deal from 2013.
It can only help Baltimore's cause that Rutschman is not a Scott Boras guy. And besides, the law of averages states that surely the club won't pull an 0-fer in its mission to secure its core.
Probability Meter: High
LHP Garrett Crochet, Boston Red Sox
7 of 10
Age: 25
2024 Stats: 32 GS, 146.0 IP, 123 H (18 HR), 209 K, 33 BB, 3.58 ERA
2025 Status: Arbitration eligible, free agent after 2026
Why It Should Happen
After what happened at the 2024 trade deadline, putting "Garrett Crochet" and "extension" in the same sentence feels akin to uttering a cursed incantation.
Of course, you can't blame the guy for wanting an extension in the event of a trade from the Chicago White Sox. It was a leverage play at a moment when he had that card to play amid an All-Star season.
Crochet is with the Red Sox now, and any willingness they have to deal with Crochet must be tempered. He is a Tommy John survivor, and one with only 219 innings in the majors.
The No. 1 upside is clearly there, however, and now is a decent time for a dice-roll on the Red Sox's part. If they wait and Crochet has another monster year, settling with just one season between him and free agency surely won't be on his mind.
But Will It Happen?
There isn't much here in the way of ambiguity. The Red Sox have reportedly discussed an extension with Crochet, whose interest is mutual.
"Staying in Boston long-term is something that has a lot of merit in my mind and something I think would be awesome," he said on January 11, per Chris Cotillo of MassLive.com.
A deal should be eminently doable for the Red Sox. They could even extend Crochet for $30 million per year and still have breathing room under the luxury tax threshold for 2025.
Probability Meter: High
LHP Tarik Skubal, Detroit Tigers
8 of 10
Age: 28
2024 Stats: 31 GS, 192.0 IP, 142 H (15 HR), 228 K, 35 BB, 2.39 ERA
2025 Status: Arbitration eligible, free agent after 2026
Why It Should Happen
Tarik Skubal was nowhere near the Best Pitcher in Baseball conversation as of June 2023, when he was still recovering from flexor tendon surgery.
Now he's in the middle of it after a 46-start run in which he's logged a 2.51 ERA over 272.1 innings. He was rightfully the unanimous winner of the AL Cy Young Award last year.
This is another case where metrics paint a picture of a guy who really is that good. Skubal was in the red for a ton of stats in 2024, with highlights including a 91st-percentile strikeout rate and a 95th-percentile walk rate.
The Tigers should want to extend Skubal just on these accounts. Factoring in that they're a contender based on pitching and situated in a pitcher-friendly park, it is that much more of a no-brainer.
But Will It Happen?
Skubal doesn't have much to say about negotiations with the Tigers, but even Scott Boras seems willing to play ball with president of baseball operations Scott Harris.
"Scott and I are going to continue to talk about him," Boras said in November. "Certainly, we have to go through the arbitration process [in January] and we'll be, I'm sure, discussing contract."
This is Boras we're talking about, so it's best to take this with a grain of salt. But given how little money the Tigers have on their long-term books, even something akin to Max Fried's eight-year, $218 million contract doesn't seem impossible.
Probability Meter: Medium
RF Kyle Tucker, Chicago Cubs
9 of 10
Age: 28
2024 Stats: 78 G, 339 PA, 23 HR, 11 SB, .289 AVG, .408 OBP, .585 SLG
2025 Status: Arbitration eligible, free agent after 2025
Why It Should Happen
With all respect to Juan Soto, Kyle Tucker is the best player to change hands this winter.
Across the last four seasons, he's been good for about a .900 OPS and 30 home runs per season. Those aren't Soto numbers, but Tucker differs in that he's actually useful on the bases and in the field, where he won a Gold Glove in 2022.
With these creds, Tucker is positioned to be the best player on the free-agent market next winter. He won't be staring down Soto money, but he could get close to halfway there if he so much as chased Aaron Judge ($360 million) or Mookie Betts ($365 million) money.
As far as the Cubs are concerned, they should certainly want to keep Tucker past 2025. He's the superstar they've been missing since the heydays of Kris Bryant, Anthony Rizzo and Javier Báez.
But Will It Happen?
Close to free agency though he may be, Tucker is not unwilling to hear the Cubs out:
The Cubs would be wise to accept this olive branch, and whether they can afford to extend Tucker shouldn't be in question.
This is a franchise with revenues in the half-billion dollar range, which is something no other NL Central team can say. Perhaps it's a fool's hope, but the Ricketts family finally taking a big swing on a player is nonetheless worth hoping for.
Probability Meter: Medium
1B Vladimir Guerrero Jr., Toronto Blue Jays
10 of 10
Age: 25
2024 Stats: 159 G, 697 PA, 30 HR, 2 SB, .323 AVG, .396 OBP, .544 SLG
2025 Status: Arbitration eligible, free agent after 2025
Why It Should Happen
Actually, there's a compelling case that the Blue Jays should not want to extend Vladimir Guerrero Jr.
He's a bat-first player whose bat doesn't loom as large as the one that scored Juan Soto a $765 million contract. There's also some volatility in Guerrero's track record, as he was merely good in 2022 (.818 OPS) and just OK in 2023 (.788 OPS).
Guerrero is still just 25, however, and last year reinforced how great he can be. It was the second time in four years that he hit over .300 and cleared the 30-homer threshold, and only Shohei Ohtani produced more hard-hit balls.
There's also the question of where the Blue Jays will go if they don't extend Guerrero. If they do, they have a star to build around for a long time. If they don't, a rebuild may be inevitable.
But Will It Happen?
As Guerrero has set a spring training deadline for a new deal, the clock is ticking. And his price tag? It's not cheap.
Bob Nightengale of USA Today and Jon Heyman of the New York Post have both put Guerrero's target in the $400 million range. That would set a record for an infielder, easily clearing Manny Machado's 11-year, $350 million contract with the San Diego Padres.
That the Blue Jays have talked and want to continue talking with Guerrero means there's a chance. But given the profile they're dealing with, you can understand why they have not come close to what Guerrero wants.
Probability Meter: Medium
Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.
.jpg?w=600 "Allen Wanted to Keep Bone 😅")
.jpg?w=600 "Steelers Owner Gives Rodgers Update")
.jpg?w=600 "Coach Questions Beck's Personality 🤔")
.jpg?w=600 "WWE NXT Results & Grades 🔠")
