Walker Jenkins, Scott Boras, and the Art of the Pre-Debut Contract Extension

[Cody Christie]

Image courtesy of © Kiyoshi Mio-USA TODAY Sports

There was a time when major-league teams treated prospects like unopened Christmas presents. You didn't lock in the value before you knew what was inside. Now, clubs are increasingly trying to shake the box, guess the contents, and sign the receipt before the wrapping paper even comes off.

Pre-debut extensions have become one of baseball’s more fascinating gambles. Teams are buying out uncertainty in exchange for long-term cost control, while players are cashing in before facing the volatility of development. It's a risk on both sides, but one that is increasingly comfortable, as front offices try to get ahead of the market.

The New Wave of Early Bets
The Seattle Mariners recently pushed that trend to a new level by locking up top prospect Colt Emerson to an eight-year extension worth a guaranteed $95 million, with a club option for 2034. The signing comes with a full no-trade clause and includes another $35 million in escalators. There’s reportedly an $8-million signing bonus, with salaries ranging from $9 million to $18 million from 2028-33.

That is the largest guarantee ever handed to a player who has yet to appear in a major-league game, surpassing Jackson Chourio’s deal by $13 million. Emerson, just 20 years old, has only nine games of Triple-A experience, which somehow makes the deal feel even more aggressive. If Emerson becomes a star, this deal looks like a bargain by year three. If not, it becomes a very expensive lesson in optimism.

Not to be outdone, the Milwaukee Brewers are reportedly finalizing an eight-year deal worth just over $50 million with prospect Cooper Pratt, including two club options worth about $15 million per year. However, the value of those options can increase via escalators. Pratt is 21 and has barely dipped a toe into Triple-A, making this extension feel even more like a projection than a reaction.

Unlike Emerson, Pratt is not coming off a season that screams superstardom. His offensive production was modest, but the underlying traits are what sold Milwaukee. Strong plate discipline, speed on the bases, and defensive reliability at shortstop give the Brewers a foundation to dream on. This is less about what Pratt has done and more about what they believe he will become.

It's worth noting that the Brewers have been here before with Chourio, whose pre-debut deal looked bold at the time and now looks like a masterstroke. The difference is that Chourio had already reached Triple-A and looked big league-ready. Pratt is still more idea than finished product. In fact, unlike Chourio, Scott Kingery, and several other players who signed pre-debut deals over the last two decades, neither Emerson nor Pratt will be promoted to the majors in the wake of these deals. They're still prospects; they've just become very wealthy ones.

The Boras Factor
That brings us to Scott Boras, baseball’s most recognizable agent and the human embodiment of “we will take this to free agency and like it.” Boras has built his reputation on maximizing value at the open market, often steering clients away from early extensions in favor of bidding wars. While his agency has softened its stance slightly over the years, the track record remains clear. Pre-arbitration extensions for Boras clients are exceedingly rare. In fact, the deal signed by Carlos González back in 2011 remains the only notable example of a Boras client signing that early.

That context makes the Pratt negotiations particularly interesting. If finalized, it represents a shift, or at least an exception, in how Boras is willing to operate. Perhaps it reflects the game's changing economics. Perhaps it reflects the Brewers being extremely convincing. Or perhaps it simply reflects that every rule has a price.

Could the Twins Try This With Walker Jenkins?
Let's turn, then, to Walker Jenkins and the Minnesota Twins. Jenkins is not just another prospect in the system. He's the kind of talent that invites bold decisions. A consensus elite prospect with the type of hit tool and overall profile that draws lofty comparisons, he is exactly the archetype teams consider for these early extensions.

If Minnesota believes in Jenkins the way Milwaukee appears to believe in Pratt, there is a path to a similar deal. Lock in cost certainty. Buy out arbitration years. Maybe even sneak in a free agent season or two. From a roster construction standpoint, it's appealing. From a risk standpoint, it's enormous.

The complication, of course, is Boras. Jenkins is represented by the same agent who has historically preferred to let value mature on the open market. Convincing Boras to agree to a pre-debut extension would require a deal that not only protects Jenkins, but also meaningfully rewards him for signing early. In other words, it would not come cheap, and it would not come easy.

Pratt got $1.35 million as an overslot sixth-round draft pick in 2023. Jenkins went fifth overall the same year, and got almost $7.2 million. That puts the two in very different situations, in terms of the leverage the team can exercise. The Twins will have a much harder time convincing anyone Jenkins belongs in their farm system than the Brewers have had keeping Pratt's ascent smooth but steady, given that team's far superior depth. Boras could and would hold the Twins' feet to the fire in a way he couldn't have done with the Brewers.

Pre-debut extensions are no longer outliers. They're becoming strategic tools for teams willing to bet on their evaluations. The Mariners and Brewers have each placed sizable wagers on young talent, hoping to secure future stars at today’s prices.

For the Twins, Jenkins represents a similar opportunity, wrapped in the added complexity of Boras. The question is not just whether Minnesota believes in Jenkins. It is whether they believe enough to challenge one of the sport’s most established negotiating philosophies.

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Should the Twins attempt a deal with Jenkins? Leave a comment and start the discussion.

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[twinstalker]

Pratt is crap, and Boras knows it.  He'll be a poor hitter and could be out of baseball by the end that contract.  Boras isn't going to do anything that doesn't allow his client to get max value.  Can we stop fooling ourselves on this subject?  You get in bed with the devil, you better be prepared for the consequences.

[thelanges5]

Boras probably makes Jenkins a no. I’d be in favor of locking up Keaschall, Culpepper, and Emma as the core of the future. Let’s do something here Tom. 

[Gamblerssoftball]

The elephant in the room is not knowing what the new CBA, when agreed upon, is going to look like. I'd be taking a cautious approach. A year from now is soon enough and we'll know a lot more about salary construction that will be expected. 

[nicksaviking]

Sorry, I get the premise, but disagree about the villain. Jenkins is the boss, not Boras. If Jenkins wants an early deal, that is literally what Boras is paid to do. 
 

Now, the reasons that Jenkins picked Boras may be the same reasons that Jenkins wouldn’t want an early deal; such as great self confidence, willingness to bet on himself, AND the fact that Jenkins was a top five pick, unlike the other two players.

But sadly, no deal is likely, but that’s mostly on the Twins. Their only priority is to sell the team and get the buyer to take the phony 500M in debt they tacked on. They haven’t given anyone a multi year deal in two years, that’s by design. They want as little committed debt tied to this lemon of an organization as possible. 

[TopGunn#22]

If I were the Twins, I'd very much want to lock Jenkins up pre-debut, even with the nightmare of what has become of Royce Lewis, a former #1 overall pick.  Scott Boras is a unique agent.  He has a philosophy of wanting to get his client to FA, even if a good deal is on the table.  Exhibit "A" is Ryan Jeffers.  

There is often talk on TD about what an above average hitter Jeffers is for a Catcher, but in reality, he's average.  No where near "elite."  Add to that his below average all around catching skills and I'm left wondering why Boras didn't initiate extension talks with the Twins.  We all know there is no way Jeffers is in a Twins uniform after this season.  The best we can hope for is some kind of value in a deadline deal, but the Twins have little leverage with Jeffers at this point.

The Brewers have been fairly aggressive in trying to buy out FA with young stars.  But frankly, rather than Cooper Pratt getting the deal he did, the guy I thought the Brewers would have locked up was 18-year old SS Jesus Made.

Pratt is a "more advanced hit tool" version of Marek Houston.  Pratt's defensive skill at SS is top shelf.  But he's baseball's #62 rated prospect beginning this season at AAA.  Made is baseball's #3 (THREE !!!) overall prospect with a switch-hitting hit tool that is tremendous.  Made has the ability to stay at SS, but with a glove like Pratt, could find himself at 3B.  A 2027 Brewer infield with Made at 3B, Pratt at SS and a Gold Glove 2B like Brice Turang is something Brewer fans can really get excited about. 

I think the Twins should be talking with Scott Boras about a Walker Jenkins contract.  But does Boras have any desire to take the phone call?  

[Western SD Fan]

My first concern would be the brain trust in developing prospects.  We are seeing in real time the consequences of not adequately developing prospects in Lewis, Lee, Wallner, and Larnach.  The two teams given as an example in the article, the Mariners and Brewers, have proven that they are better at developing high draft picks into viable major league players than the Twins.  

Top players from Mariners drafts since 2017:  2018: Logan Gilbert & Cal Raleigh, 2019: George Kirby, 2021: Harry Ford & Bryan Woo, 

Top players from Brewers drafts since 2017:  2018: Brice Turang, 2021 Sal Frelick, 2022 Jacob Misiorowski, 2023 Cooper Pratt

Although not mentioned in the article, there are rumors that the Pirates are working on a similar contract for Konnor Griffin.  Even the Pirates have had a better draft and development of players than the Twins.

All of that to say that if you have a proven record of draft and development, the risk of locking up these young players may be worth it compared to a team like the Twins who does not have the same record of success

[terrydactyls]

A question popped into my head about player development.  (And having an interesting thought by me before noon is very rare.)  Quite a few people claim that other teams "develop" players better than the Twins.  That may be true.  However, what if the Twins are so bad at evaluating draft-eligible players that the real problem is the lack of talent available to "develop"?

[saviking]

The Colt Emerson deal would be a no brainer for the Twins but if I was Walter Jenkins I would bet on myself. 

[jmlease1]

Boras is never going to engage in extension talks for Walker Jenkins unless Jenkins orders him to do it or be fired. 

Now, players change representation all the time, but there's usually something behind it, and there's no indicators that Walker Jenkins is unhappy with his representation, and as a high draft choice, has less need to get an extension put in place: he's got money, enough that he doesn't need to do things like room with another player unless he wants to, and certainly doesn't need to work another job in the offseason. Jenkins has also been rising fast and well in the minors, so there's little chance of him busting before reaching MLB, and the MLB minimum salary is now pretty damn significant as well.

It's pretty easy to see why Walker Jenkins would listen to his agent if they said "you don't need an extension, you're going to make a lot more money if you wait, and you're going to have a lot more control if you go to free agency." It might not be best for the Twins or what fans want, but neither of those parties has Walker Jenkins and his life as their number one priority. (you can argue that the agents are just as self-involved as anyone and care more about the payday than the player, but as long as the agent only gets paid if the player gets paid, they're going to have the advantage in the "trust me" category.)

Boras wants his clients to go to free agency. he thinks it's better for them individually, and the players collectively. YMMV on whether that's true or not, but he's had a lot of success and has a very strong reputation for getting players paid. I suspect more players leave his firm because they start feeling like they're less of a priority or they want more hands on work from the principal rather than a junior, more than "Boras didn't do right by me on my contract". He clearly wants multiple teams bidding on a player, and wants the teams that have the most resources to be in play. he cares nothing for competitive balance, the woes of smaller market teams, the wants of a fanbase...none of it. Not his job, not his problem. (this gets wobblier when he and other agents try to control the CBA negotiations, but again YMMV)

Bottom line: Walker Jenkins ain't signing an early extension. The best we might see if a buy-out of arbitration years (if those still exist in the next CBA) at roughly market-rates to get to FA, providing cost certainty. But still it's unlikely.

[DJL44]

The Twins have stated they think Keaschall is a future All-Star but they haven't tried to lock him up. They didn't extend Jeffers when it was an obvious decision. I have no confidence in this front office's ability to do anything except watch the waiver wire to "upgrade the floor".

[Linus]

2 hours ago, terrydactyls said:

A question popped into my head about player development.  (And having an interesting thought by me before noon is very rare.)  Quite a few people claim that other teams "develop" players better than the Twins.  That may be true.  However, what if the Twins are so bad at evaluating draft-eligible players that the real problem is the lack of talent available to "develop"?

Correct in my view. First of all it’s normal for prospects to fail, even good ones. But when you look back on some of the draft selections the Twins have made, their overall physical abilities appear to have been more limited. 

[SteveLV]

Jenkins comes from a solid, faith-based family in coastal North Carolina.  I don't think he is the personality type to try and break the bank, and might take the personally conservative approach of taking a guaranteed deal in exchange for his arb years.

But I don't think Twins current ownership has any interest in long-term financial commitments, no matter how prudent they might be. They apparently want to keep the books clean.  Same reason they are not extending Joe Ryan.