Superagent Scott Boras is often hailed as a master negotiator, securing record-breaking contracts for his star clients. But the recent Blake Snell deal raises questions about whether Boras’ touch may be slipping. Snell, fresh off a Cy Young Award-winning 2023 season, could only manage a two-year, $62 million contract with the San Francisco Giants.

This comes as a disappointment for a pitcher with two Cy Youngs already under his belt, especially after he reportedly turned down longer, more lucrative offers. Does it hint at a gamble that didn’t pay off, or is there a deeper strategy at play?

Boras is known for playing the long game, holding out for top dollar, and encouraging his clients to bet on themselves. This strategy might have paid off handsomely in the past, but the current market dynamics seem to have worked against him. As Ken Rosenthal of The Athletic notes, an anonymous agent recently reflected on how “The Titanic had fewer people thrown overboard than the SS Boras.”

Rosenthal sees Boras-Three’s short-term contracts as an upside play. Cody Bellinger, Matt Chapman, and Blake Snell could hit it big again if they dominate. But there’s no room for errors this season. They have to prove it every year—especially Snell, who’s chasing another big payday despite already having two Cy Youngs.

Snell’s Cy Young seasons of 2018 and 2023 speak of a story of dominance, with low ERAs (1.89 and 2.25), high strikeout rates (221 and 234), and impressive win percentages. However, therein lies the question of his inconsistency.

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Blake Snell can be brilliant on the mound, but he also has a tendency to walk batters, raising concerns about his control and stamina. It’s this unpredictability, coupled with a qualifying offer with added draft pick penalties, that likely deterred teams from offering him the longer contract he desired. While the current deal itself may not have been ideal, there are reasons to believe Snell can thrive in San Francisco.

The Giants: A silver lining for Blake Snell?

Despite the underwhelming contract, the move to San Francisco isn’t a complete bust for Snell. While the division is tough, the Giants’ rotation now boasts the likes of Logan Webb and Alex Cobb, along with young star Kyle Harrison and their latest acquisition in Robbie Ray, providing the ace with a solid foundation. Plus, playing in a notoriously pitcher-friendly park could help him regain the consistency that propelled him to previous Cy Young levels. Could this year turn out to be Snell’s path to redemption?

In the eyes of the league, Snell has something to prove. With a strong performance in 2024 (FanGraphs projects a 30.0% strikeout this year compared to ’23’s 31.5%), he can opt out and re-enter the free-agent market with less baggage. But that success won’t come easy.

Boras will need to recalibrate his strategy, and Blake Snell will have to demonstrate that he can consistently deliver ace-worthy numbers. Right now, it’s too early to definitively call the Snell deal a loss for Scott Boras. However, it’s a clear sign that his usual playbook may need an update.

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The current free-agent market appears less willing to overpay for past success and potential, placing a higher premium on recent consistency. For both the agent and his client, this deal serves as a valuable reminder that even in the world of high-stakes baseball contracts, nothing is guaranteed.