Monday’s deep dive into Paul Skenes, perhaps the most interesting extension case in baseball, was a sneak peek of Extension Week.

Now I’ll start a broader look at potential extension candidates, concentrating today on players whose value is less speculative: impending free agents.

These players are, in general, less likely to sign an extension with free agency waiting at the end of this season, and my analysis here is basically projecting what each player could earn on the open market before adding in his 2025 salary. If nothing else, it’s an early projection for a free-agent deal this upcoming winter.

Since last spring’s Extension Week, three players actually put pen to paper on an extension, all earning a bit more than I projected:

*Here and in all other tables, I’ll account for significant deferrals by using the present-day value of the contract when it was signed.

I’ve tried to factor that into the analysis this year.

Here’s how I go about this: I’ve got a big Excel spreadsheet with more than 1,100 free-agent and extension contracts in it, as well as players’ performance in the years leading up to those contracts, as defined by FanGraphs’ wins above replacement. Whereas players get paid off home runs and saves in arbitration, I’ve found fWAR to be a solid (though not all-knowing) predictor of earnings on the open market.

I plug extension candidates into the spreadsheet, find players with similar levels of production (and ideally with similar amounts of team control left) before they signed their deals, and work off of those comps.

A few overall points worth remembering:

• For extensions, team control is important. If Player A looks just like Player B, except Player A has three years of arbitration ahead of him and Player B was a free agent, Player A isn’t going to get the contract Player B did. However, what Player B made in free agency is still useful as a guide to what the later part of Player A’s contract can look like.
• For starting pitchers and position players, I look at fWAR in one-, three- and five-year samples, with a special emphasis on the shorter term. For extensions in particular, the five-year sample is less helpful because a lot of players haven’t been playing for five full years.
• For relievers, I look at one- and two-year samples. What happened five years ago isn’t really relevant for such a volatile position, and I’ve found more of a recency bias in contracts here than elsewhere.
• This is an exercise in player valuation, not commentary on the likelihood of an extension being signed or whether I think a team or player should sign an extension at the value I suggest. I find doing this helpful even when an extension is unlikely because it helps me understand what the market may be once a player reaches free agency or to see how the player’s value has changed over time.

As we go through this, keep in mind:

• The actual extension projection in all cases includes what the player is slated to make this season. It will likely contain a lower AAV (average annual value) than the player would get on the open market for this reason.
• These players should have higher projections this year than last year. Last year, they were two years removed from free agency, and they were slated to make below market value via arbitration.
• The number in parentheses is the player’s age on July 1 of this year.
• In the charts, “Today AAV” is the average annual value of the deal adjusted for inflation.
  

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Vladimir Guerrero Jr. (26)

Maybe no one in baseball had a better year for their potential earnings than Guerrero. His 5.5-win season (according to FanGraphs) washed away any concerns after a pedestrian 2023 and reminded the sport that he’s one of its very best hitters. Plus, a player with similar strengths and weaknesses signed for more than $750 million. So Guerrero is in significantly better shape this spring than he was last spring.

Earlier in spring training, I broke down why Guerrero’s value in an extension has proven difficult to pin down. At the moment, he looks like he belongs just below the second tier of free-agent contracts for first basemen (Miguel Cabrera is the sole occupant of the top tier).

Extending a deal for a massive 14 free-agent years would limit the AAV just a touch, to about $30 million. I know, I know: A deal that long comes off as crazy. But there have been a dozen players who have signed deals at least nine years in length in the last three offseasons — or just shy of the number of contracts that long that were signed over the prior decade. Four of them (Juan Soto, Trea Turner, Manny Machado and Xander Bogaerts) extend through a player’s age-40 season, as this one would for Guerrero.

2024 extension projection: Seven years, $185 million
2025 Salary: $28.5 million
2025 extension projection: 15 years, $450 million

Kyle Tucker (28)

If Tucker had remained healthy last season and continued playing the way he did in the first half of the season, his best statistical comp would be… Soto. Because of his age, Tucker wouldn’t have been able to get as long a deal as Soto, but he would have been able to make a case for a similar average annual value.

The comps are not bad as is.

Tucker should be able to secure a deal through at least his age-36 season, and it’s not hard for him to argue he should go longer than either Teixeira or Fielder. Let’s go with 10 years at about $35 million each before adding in this season’s salary.

2024 extension projection: Eight years, $204 million
2025 salary: $16.5 million
2025 extension projection: 11 years, $366 million

Dylan Cease (29)

Last season, Cease and Zac Gallen entered in a similar spot: at the same age, earning about the same in arbitration, in line for about the same extension. Then, while Gallen had a nice season, Cease posted another top-five finish in the Cy Young balloting. He’s placed himself in the same group as the top earning starters from this past winter.

Lester sets the high end for Cease, and that comp suggests Cease can in fact get more than Burnes just did from the Diamondbacks. Both point to a deal buying out six free-agent years. Let’s estimate those at just under $33 million and add in this year’s salary.

2024 extension projection: Seven years, $140 million
2025 salary: $13.75 million
2025 extension projection: Seven years, $210 million

Zac Gallen (29)

Right now, Gallen isn’t quite on the same level as Cease.

This sets him up for roughly the 2025 version of Cueto’s deal in free agency: six years and $174 million, before adding this year’s salary.

2024 extension projection: Seven years, $140 million
2025 salary: $13.5 million
2025 extension projection: Seven years, $187 million

Framber Valdez (31)

Valdez has had just as much success as Cease and Gallen; the issue for him is he’s two years older than those guys. Starters who hit the open market entering their age-32 season seldom sign for more than three or four years. (The exceptions are guys like Zack Greinke, CC Sabathia and Cliff Lee, who all owned Cy Young awards.)

Let’s stick with the same comps as Gallen but only for four free-agent years rather than six.

2024 extension projection: Five years, $105 million
2025 salary: $18 million
2025 extension projection: Five years, $134 million

Devin Williams (30)

Just looking at the raw numbers isn’t charitable to Williams, who on a per-appearance basis is right there with recent closers who signed four-year deals like Raisel Iglesias and Tanner Scott. (Williams missed roughly two-thirds of last season.)

Given that no position gets paid on reputation quite the way closer does, Williams could still be in line for a deal that rivals Scott’s, before adding in this year’s salary.

2024 extension projection: N/A
2025 salary: $8.6 million
2025 extension projection: Five years, $80 million

(Top photo of Dylan Cease: Orlando Ramirez / Getty Images)