In what has been a somewhat underwhelming offseason for Scott Boras and his cohort of star clients, the quartet of players including Matt Chapman, Cody Bellinger, Blake Snell, and Jordan Montgomery have seen their respective markets progress at a sluggish pace. While Chapman and Bellinger have found teams to call home, Snell and Montgomery still await their deals.

Chapman, the talented third baseman, has inked a deal with the San Francisco Giants, while Bellinger has reunited with the Chicago Cubs. Snell, the former Cy Young Award winner, is reportedly on the verge of joining Chapman in San Francisco, according to multiple reports. The only player from Boras' group remaining without a contract is Montgomery, and his signing does not seem imminent at the moment.

However, it is worth noting that the reported contract figures for Chapman, Bellinger, and Snell have fallen well short of initial projections. Snell's prospective deal with the Giants, which technically spans two years, could be worth around $62 million. However, the contract includes an opt-out clause after the 2024 season, allowing Snell to test the free agent waters if he replicates his standout performance from 2023 when he won the NL Cy Young Award as a member of the San Diego Padres.

MLB Trade Rumors' projections for the Boras foursome now seem almost comical when compared to the actual contracts they received. As Opening Day looms just over a week away, it is highly unlikely that Montgomery is fielding a six-year, $150 million offer. Nonetheless, this deviation from expectations should not undermine the work done by the analysts at MLB Trade Rumors, as the actual deals often fall short of both Boras' desires and demands.

Considering Snell's contract structure, it is plausible to assume that Montgomery's eventual deal will bear some resemblance to it. While Snell is a more accomplished pitcher, both left-handers are 31 years old, providing a reference point for Montgomery's negotiations. It is probable that he will sign a short-term contract with opt-out options incorporated at various points. A theoretical deal of two years and $55 million, with an opt-out after the first year, seems feasible.

Rumors surrounding Montgomery's potential landing spot have been abundant, with particular attention paid to the Boston Red Sox. The Red Sox executives, including CEO Sam Kennedy, have expressed interest in the 2023 World Series champion, while also acknowledging financial limitations. Staying under the competitive balance tax (CBT) appears to be a priority, as the team's current payroll stands at $213 million, excluding potential raises for players like Roberto Perez, Lucas Luetge, or C.J. Cron upon inclusion in the major league roster.

If Montgomery were to command a salary in the range of the suggested $27.5 million per year, the Red Sox would likely need to make additional moves to remain under the CBT threshold, assuming that remains their financial objective. While a discounted rate and shorter contract duration make Montgomery more appealing, the Red Sox have been hesitant to offer long-term contracts to pitchers above the age of 30. The prospect of a two to three-year deal is considerably more attractive than a lengthier commitment.

However, it is not just the Red Sox who have shown interest in Montgomery. The shifting parameters of the market, in which prices are decreasing for many teams, could potentially lead to increased interest in the left-handed pitcher. Teams like the New York Yankees, who are familiar with Montgomery and may need pitching reinforcement due to an injury to ace Gerrit Cole, could enter the fray. The Houston Astros, Texas Rangers, and St. Louis Cardinals, all familiar with Montgomery's abilities, could also be potential destinations.

While the Red Sox clearly believe they can exceed expectations in 2024, their odds of winning the World Series currently stand at 65-1, longer than 20 other teams in the league. Many of these teams could afford a shorter-term deal and, if they were to contend for a championship, this becomes even more enticing for a player like Montgomery. It would provide him with a chance to solidify his status as a clutch performer and potentially opt out after the season, restarting the free agency process.

If the Red Sox fail to secure Montgomery's services this offseason, a Snell-like deal could allow them another opportunity to pursue him in the near future. If the timing is not right now, the team's hope will be that significant improvement in the 2024 season could position them as legitimate suitors once again when frontline pitchers like Montgomery become available.

As the remaining pieces of the offseason puzzle come together, it remains to be seen where Montgomery will ultimately find his next team. The slow market has presented challenges for Boras' clients, but as deals are finalized and contracts are signed, the landscape is gradually shaping up for the 2024 season.