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It’s typically not wise to enter a staring contest against Scott Boras.

Baseball’s super-agent rarely cedes control of the industry’s transactional season, from his strangely endearing dad jokes to kick off the general managers’ and winter meetings to his ability to wait out an ostensibly disciplined owner or GM who will finally capitulate to his expectations.

Yet here we are, just three weeks from Opening Day, the clocks ready to spring forward and two of his elite clients – left-handed pitchers Blake Snell and Jordan Montgomery – remain unsigned.

Two more received below-market guarantees laced with opt-outs, pacts that amount to prove-it deals after Cody Bellinger (three years, $80 million, Cubs) and Matt Chapman (three years, $54 million, Giants) finally signed with clubs long expected to land them – for far less than projected.

What happened to the Boras Four?

HOT STOVE UPDATES: MLB free agency: Ranking and tracking the top players available.

With the actual season just around the corner and the hot stove nearly shut off, a look at the forces that combined to freeze out a significant chunk of the game’s free agent market:

Imperfect gems

While every free-agent season takes on a unique and sometimes unpredictable rhythm, Boras has excelled at the long game.

Max Scherzer (Jan. 21, 2015), Prince Fielder (Jan. 24, 2012) and Bryce Harper (Feb. 28, 2019) are the most notorious beneficiaries of patience – signing deals between $210 million and $330 million long after the New Year’s fireworks fade.

Like Harper, Bellinger had an MVP award on his mantle when he hit the market. Snell has two Cy Young Awards – one in each league and one more that Scherzer possessed at that point.

So why the bargain-bin treatment?

Perhaps that question won’t be fully answered until this 2024 season plays out, and Boras said Monday that four new teams expressed interest in his unsigned pitchers in the past week.

Yet each of the Boras Four have mild to moderate drawbacks that kept them from naming their price.

Snell entered free agency as the reigning NL Cy Young winner after leading the major leagues in ERA (2.25), adjusted ERA (182) and fewest hits per nine innings (5.8). He struck out 234 batters in 180 innings.

Yet there were reasons teams might give pause at awarding Snell a nine-figure deal – a price tag that seemingly shot up after Yoshinobu Yamamoto’s record-breaking $325 million deal with the Dodgers.

Snell also led the big leagues with 99 walks, posting a 5.0 walk rate that was the worst since his 2016 rookie year. Snell clearly was able to punch out of self-inflicted hot spots but should his K rate deteriorate and his walk rate endure, those jams will be problems going forward.

He’s also not enjoyed the linear success teams like to see when making a massive commitment. Snell’s 2018 and ’23 Cy Young bookends were almost identical, from ERA (1.89 and 2.25), innings pitched (180 ⅔ and 180) and hits per nine (5.6 to 5.8). It’s fair to say that represents his peak – and even then, he averaged less than six innings a start.

In the four full seasons in between? A WHIP that ranged from 1.20 to 1.32 and a pair of 4-plus ERA campaigns.

Bellinger’s health woes have been well-documented – shoulder surgery after the 2020 season, and a fractured fibula in 2021. It takes a minute to rebuild both your upper and lower halves as a hitter.

And it seemed like Bellinger did so in 2023, when he hit 26 homers, produced a .307/.356/.525 line and 4.4 WAR. Still, injuries limited Bellinger to 130 games, and his batted-ball data did not back up the profile of a 28-year-old slugger in his physical prime.

Chapman’s arrival in Giants camp turned his pitchers giddy, knowing that the left side of the infield will be gobbled up by a two-time Platinum Glove winner whose defense largely accounted for, like Bellinger, 4.4 WAR in 2023.

But Chapman’s offense tailed off badly in his final year in Toronto, hitting a career-low 17 homers with a 108 adjusted OPS that’s barely north of league average. His OBP in two years as a Blue Jay was .327.

Montgomery is perhaps the most interesting case – never an All-Star, never hit 200 innings or 200 strikeouts, but what a compelling finishing kick. He produced a 1.09 WHIP after a midseason trade to Texas and turned in a solid postseason; the Rangers won his starts in a pair of Game 1s and also Game 7 of the ALCS as they captured their first World Series.

How much is a quality-start machine who lands just shy of an ace worth? We’re still waiting to find out.

Passive aggression

With the Shohei Ohtani and Yamomoto chases commanding the attention of fans and the biggest markets, it stood to reason that the Boras Four would make nice, high-priced consolation prizes for the sweepstakes losers.

Yet too many teams decided to tap out. They may regret it.

The Blue Jays were viewed as excellent fits for Bellinger and to reunite with Chapman. Yet they opted to run it back with Kevin Kiermaier in center, choosing elite defense and an easy-to-swallow $10.5 million commitment rather than the promise that Bellinger might someday approach his 47-homer form of 2019.

The Chapman pivot is more curious. Toronto will throw a mélange of bodies at third, second and DH, from Isiah Kiner-Falefa to Cavan Biggio to Santiago Espinal, 39-year-old Justin Turner and perhaps Eduardo Escobar.

The Blue Jays had firsthand experience with Chapman’s hitting woes and, after a lineup-wide offensive struggle in 2022, perhaps decided the elite defense wasn’t worth it. They also have longer-term concerns retaining All-Stars Bo Bichette and Vladimir Guerrero Jr. after 2025, which could be complicated by making other multi-year commitments.

The Giants’ patience did pay off in landing Chapman but they threw a wrench in Bellinger’s market by signing Korean center fielder Jung Hoo Lee (also a Boras client) to a $113 million contract. And it’s clear much-needed rotation additions won’t happen unless Snell or Montgomery both opt for a short-term deal, a la Chapman.

Meanwhile, the player market has not benefited from the Boston Red Sox’s ambivalence toward free agency in recent years. They’re a consensus choice to finish last in the AL East for the third time in the last five years, an outlook that would brighten a bit if they signed Montgomery.

They're also clearly willing to, at best, wait it out and sign Montgomery at a bargain rate, never mind the risk of losing him.

The starting pitching stable is only a little bit deeper next winter, with Corbin Burnes, Max Fried, Walker Buehler and Shane Bieber due to hit the market. That crop thinned Monday, when Phillies ace Zack Wheeler agreed to a three-year, $124 million deal, a per-year record for a contract extension.

Eventually, you gotta pay for arms.

Future shock

These aren’t quite the dark days of 2017-18, when market ambivalence left dozens of useful veterans seeking jobs well into February, prompting the MLB Players’ Association to open a spring camp for unsigned players.

Nor is it accompanied by as much saber rattling as the collective bargaining agreement between MLB  and the union nears the midterm. Yet there’s a certain wariness out there.

After re-signing with the Los Angeles Dodgers, utilityman Kiké Hernandez made thinly-veiled references to collusion – not just for the itinerant player, but also the Boras Four – on a podcast interview. MLBPA executive director Tony Clark called the unsigned status of several stars “interesting,” which on his scale of verbosity is not insignificant.

The very real cable TV/streaming crisis facing the game – currently and beyond – undoubtedly affected certain teams’ budgets. Yet from the labor perspective, there’s once again a line separating actual concerns with excuse-making, one that management is loathe to reveal.

That line isn’t going away anytime soon, much to the chagrin of the Boras Four. After all, the opt-out clauses in their deals are designed to reestablish value and take another crack at free agency.

Which means one year from now, going through this all over again.