In the offseason leading up to the 2019 MLB season, Scott Boras had seemingly reached the peak of his career.
He had just secured two massive contacts for two of his biggest clients, Manny Machado and Bryce Harper.
Boras secured Machado a 10-year contract with the San Diego Padres worth $300 million and Harper a 13-year contract worth $330 million with the Philadelphia Phillies.
Boras played the waiting game and secured $630 million for just two clients.
Fast forward five years later when Boras seemed to try the same approach again with his big-name free agents and he came up flat, potentially leaving millions on the table for his clients.
Former Toronto Blue Jays third baseman Matt Chapman and former San Diego Padres starting pitcher Blake Snell turned down longer-term nine-figure contracts as they sought even bigger deals.
Then this month Chapman and Snell agreed to short-term deals with the San Francisco Giants, worth $54 million and $66 million respectively. Both contracts are a far cry away from the long-term guaranteed money Boras had touted for them.
Although those two were the most noticeable clients of his to come up short on their desired contracts, they weren’t his only clients receiving lower returns.
Former N.L. MVP Cody Bellinger failed to have his desired long-term contract offer met and reigning World Series champion starting pitcher Jordan Montgomery signed only a one-year contract on March 26.
Boras has played the waiting game and lost at every corner this time.
And the deck might have been stacked against him from the beginning.
In recent years, baseball has shifted to a more analytic approach.
And using Chapman and Snell as examples, despite the accolades they’ve both accumulated in their careers, both have noticeable flaws that would cause teams to question the valuations Boras had for them to start the offseason.
Chapman is a great defender and has solid power, but he has issues making consistent contact, as he ranked in the lowest 16th percentile in strikeout rate and the lowest 18th percentile in whiff rate, according to Baseball Savant.
And Snell, although winning his second Cy Young award, has his flaws with issuing walks, as he ranked in the lowest fourth percentile in 2023.
Player performance aside, this offseason brought forth some challenges in team finances.
Some big market teams, such as the Boston Red Sox, opted to focus on shedding payroll to avoid the penalties of crossing the luxury tax threshold.
Others faced their broadcasting revenues being in jeopardy, as Bally Sports, the broadcasting partner for nearly half of the league, faces a grim financial future.
The teams hit the hardest by this were two teams with postseason aspirations this season, the Minnesota Twins and the San Diego Padres.
While they would traditionally be in a competitive position to spend in free agency, the lack of television revenues saw teams like Minnesota and San Diego shed payroll rather than add.
This meant there were less competitive teams to drive up the price for Boras’ big-name clients and start bidding wars between each other.
Boras was set in his old ways this offseason and it’s cost his clients millions.
The league has changed and for the sake of its players, it’s time for baseball’s biggest agent to adapt.