Scott Boras’ Big 4 Officially Inked: Where Did the Contract Maestro Falter This Free Agency?

Scott Boras, known throughout baseball as a powerbroker with a reputation for securing record-breaking contracts for his clients, has faced an unexpectedly challenging free agency season in ’23-’24. His strategy of holding out for lucrative long-term deals has collided with a market that seems to be shifting away from the mega-contracts of the past. And the result?

The famous “Boras Four”—Jordan Montgomery, Blake Snell, Matt Chapman, and Cody Bellinger—all settled for shorter-term, less lucrative deals this season, leading to intense scrutiny and raising questions about Boras’ future. Was this a blip on the radar or a sign of a changing tide in player negotiations?

The Changing Face of Baseball’s Free Agency

A confluence of factors seems to have created this challenging market for Boras and his clients. First, there’s a clear financial shift. “All of our models have predicted there are market lulls after spending,” Boras himself acknowledged to The Associated Press, referencing a reported billion-dollar drop in overall free-agent spending this year. This suggests some teams are tightening their belts, unwilling to commit significant resources in a market with less certainty.

Secondly, the way teams assess players has changed dramatically. Gone are the days when a single stellar season guaranteed a massive payday. Advanced analytics now delve into a player’s age, consistency, and injury history, creating a more cautious approach for teams, especially when evaluating older players with outlier seasons.

“These are $30 million players,” Boras says. “How many teams are really going to be involved (for a Cy Young or MVP player)? That is a small group of owners. It’s not about 30 teams, it’s about five or six.” This highlights his understanding of the market’s contraction, but it also suggests he might have underestimated the extent to which analytics have driven this shift.

The dominance of shorter-term deals with opt-out clauses for Boras’ clients further underscores this point. Teams are prioritizing flexibility, wanting to see a player repeat their success before committing significant long-term dollars. This strategy, however, comes at a cost for his players, who forgo guaranteed long-term security in exchange for the chance to potentially earn a bigger contract after a strong season. Will this gamble pay off?

We’ll have to wait and see. But one thing is clear: the days of Boras simply dictating the terms of free agency contracts seem to be over. The industry has spoken, and it’s demanding a more cautious approach. Boras seems to have misjudged the market. But could there be a hidden strategy?

Scott Boras’ Signature Strategy Backfires

Boras’ negotiation strategy has long been admired for its ruthlessness and effectiveness. He’d typically hold out for the very best offer, leveraging bidding wars between teams desperate to sign his star clients. This strategy has secured some of the biggest contracts in baseball history. However, this free agency season exposed some cracks in the foundation. While the superagent acknowledges a cyclical nature to spending, some might believe that he underestimated the depth of the change.

“We’ve had two years where they’ve spent $3.5 (billion) to $4 billion. Usually in a five-year model, we’re going to see ownership use that in their consideration,” Boras says. However, a drop of a billion dollars in free-agent spending this year suggests a more fundamental shift in team priorities.

“The reason players want long contracts is because they age, like everyone else,” commented one EssentiallySports’ analyst. “There is nothing to say that Snell is going to have another Cy Young year,” said another. This sentiment, echoed by others, suggests that Boras’ clients, some on the wrong side of 30, may not have been the best fits for the long-term deals he was seeking and that his strategy may need to adapt to this new reality.

Beyond the market shift, it’s not impossible to believe that Boras may have simply overestimated the value of some of his clients. Yes, he did get his clients the exact AAV or something closer to what they were seeking on those short-term deals—but at what cost?

Read More: Scott Boras’ Top Clients to Fall Short of Yoshinobu Yamamoto’s $325 Million Pact? Super Agent’s Miscalculations Backfire

For instance, Blake Snell reportedly turned down a six-year, $150 million offer from the New York Yankees earlier in the offseason. He eventually signed a two-year, $62 million deal with the San Francisco Giants. While the AAV is comparable, the overall guarantee is significantly less. This raises questions about whether Boras’ strategy of waiting for the “perfect” offer ultimately backfired for some of his players. Did this cost his clients valuable dollars? We may have to look to the unseen hand of player choice to find the answer.

The Unseen Hand of Player Choice

While Scott Boras is often the face of negotiations, it’s important to remember that players ultimately hold the reins. This free agency period highlighted a potential shift in power dynamics, where players are increasingly willing to consider options beyond simply chasing the longest, most guaranteed contracts.

Boras himself acknowledges this. “We give players decisions that maybe most agents wouldn’t,” he says. “(We’ve) heard it all, done it all, been judged, but the key thing is that we give players decisions that maybe most agents wouldn’t, because we give them optionality as opposed to total guarantee.” This approach is evident in the deals secured by his clients.

Take Blake Snell, for instance. According to The Press Democrat, Snell himself admitted to pestering Boras less frequently about a deal as the offseason wore on. The ace seemed to prioritize getting ready for the season and expressed a newfound comfort level with the Giants after continuous conversations with their President of Baseball Operations, Farhan Zaidi. Ultimately, the two-year deal with an opt-out clause allowed him to control his future while securing a significant annual salary.

“With Farhan’s interest and how much I kept hearing his name come up in conversations with Scott, he just pushed me to want to come here more because of how much he was trying to get me here,” the pitcher stated. This sentiment suggests that Boras might be adapting his strategy to accommodate a player base that values flexibility alongside financial security.

Certainly, it’s logical to remain skeptical of the wisdom of these short-term deals. The potential pitfalls highlight the fact that as players age, the risks of decline or injury increase, making long-term contracts more appealing despite a potentially lower AAV. Opting for flexibility might give a player the chance to cash in after a great season, but it also leaves them vulnerable to a down year and a significantly less favorable negotiating position later.

This raises an interesting question: Is this a new era of player empowerment or simply a gamble on a volatile market? The answer likely lies somewhere in between. While players seem more willing to consider shorter deals, the long-term effects on their careers remain to be seen. However, the response from the overall market has led Boras to double down on his approach, insisting that the current system is beneficial for players.

Scott Boras Remains Defiant

Despite the scrutiny, Boras refuses to admit any errors. He attributes the current landscape to the cyclical nature of free agency spending, pointing to past boom years to bolster his argument. He believes these cycles will continue, and his focus on maximizing long-term value for his clients will eventually pay off.

Furthermore, Boras contends that the MLB’s current Collective Bargaining Agreement (CBA) provides ample opportunity for players at all levels. He emphasizes the importance of free agency and arbitration rights, which allow players to negotiate their value. “The right of free agency for mid-level players is there for them. I’ve had a number of pitchers in their 30s who have very good contracts because the demand for pitching is great,” he argues.

“We created a $50 million pool for them that didn’t exist before, and the arbitration right has been preserved. Any of those players can seek any value they so desire.” Here, Boras seems to be implying that the system isn’t broken and his clients simply weren’t a fit for the current market conditions. However, his unwavering confidence clashes with the reality of the situation.

Read More: Dubbed Baseball’s ‘Most Hated Man’, Is Scott Boras an Unsung Hero of Players’ Rights?

The shorter contracts with opt-out clauses suggest a different story. Perhaps Boras is downplaying the significant shift in the market, or perhaps he’s strategically optimistic in the face of adversity. One thing is certain: Boras’ negotiation tactics will be under intense scrutiny as he enters the next round of free agency talks. This begs the question: Is there any discontent within the MLB Players Association (MLBPA) about the recent turn of events?

What Do the Officials Say?

While the signings are complete, the discussion among players and observers is far from over. A recent player representative-led attempt to change MLBPA leadership suggests dissatisfaction with the union under Tony Clark and Bruce Meyer, leading some players to feel that there’s too much influence from star players and their agents—specifically Boras.

Harry Marino, a key figure in organizing minor leaguers, has been vocal in his criticism, taking aim at Boras’ focus on a select few: “The players who sought me out want a union that represents the will of the majority. Scott Boras is rich because he makes—or used to make—the richest players in the game richer.” This sentiment highlights a key question: did Boras prioritize short-term gains over long-term security for his super clients?

If it isn’t already evident, the question of security is paramount, especially for pitchers like Snell and Montgomery who are entering their thirties. However, it can also be possible that the players themselves may have played a role in the outcome, opting for shorter deals with opt-out clauses that give them a chance to regain leverage if they perform well this season. If any of the Boras Four players can replicate their past success, they could be in line for a much bigger payday next time around.

Ultimately, the debate centers on whether Boras’ strategy truly served the best interests of his clients. While some players may be content with the flexibility of shorter deals, others likely yearn for the long-term security of traditional contracts. This internal conflict highlights the complexities Boras faces as he navigates a changing free-agent landscape. As we turn to his future, it’s clear that he’ll need to adapt his approach if he wants to maintain his reputation as baseball’s preeminent negotiator.

The Road Ahead for Boras

The upcoming 2025 free-agent class will be a critical test. With high-profile players on his portfolio like Juan Soto, Corbin Burnes, Pete Alonso, and Alex Bregman expected to hit the market, Boras will have an opportunity to prove his detractors wrong. But if those players also see lackluster deals, it could mark a major shift in how baseball’s top agents negotiate. Will Boras need to adapt and incorporate analytical insights into his negotiation strategies to succeed in this changed landscape?

The superagent has publicly dismissed the role of analytics in player valuation, suggesting it disrespects a player’s entire career. However, completely ignoring this data-driven approach may not be a winning strategy. Finding a way to bridge the gap between traditional scouting and advanced metrics might be key to Boras’ future success. Perhaps he can leverage his experience to identify undervalued players who possess the intangibles that traditional analytics might miss, while also acknowledging the importance of a player’s statistical profile in today’s market.

Read More: Scott Boras’ Miscalculations Impact Free Agency? Super Agent’s Stalled Negotiations Enter Spring Training Amidst Prolonged Talks

His recent attempt to oust MLBPA leadership suggests a growing desire for change among players. While some might see this as a direct challenge to Boras’ influence, it could also be an opportunity for collaboration. He has consistently emphasized “optionality” for his clients, highlighting the benefits of shorter deals with opt-out clauses. This aligns with the apparent desire of many players to control their own destinies and re-enter the market sooner rather than later. By embracing this trend and working more collaboratively with players to understand their individual goals, the man might be able to maintain his influence in a new era of player empowerment.