There is a reason why uber-agent Scott Boras always advises his players to wait until free agency instead of signing contract extensions.
Yes, an extension can change a young player’s life for good, but the best earning opportunities are in the open market, where the other 29 clubs can bid if they want to and the price goes up.
Before the 2019 season, he signed a six-year, $120 million extension with an opt out after 2022.
He gave the Red Sox four excellent seasons under a team-friendly deal for a player of his caliber.
Now, his contract stipulated he had a chance to test free agency after the fourth year, and he is taking it.
A player of his talent could be making around $30 million per year, not $20 million, so it’s only logical he pursues that chance.
The Red Sox Have Been In This Position Before
A few years ago, a former Red Sox great was in the same position as him.
“The Bogaerts situation is reminiscent of what happened with Jon Lester, who rejected a $70m offer from the Red Sox and got $155m from the Cubs later in the same year,” MLB insider Buster Olney tweeted.
The Bogaerts situation is reminiscent of what happened with Jon Lester, who rejected a $70m offer from the Red Sox and got $155m from the Cubs later in the same year.
— Buster Olney (@Buster_ESPN) November 30, 2022
Lester won the 2013 World Series with the Red Sox and is a franchise great.
But he had to think about his best interests and not necessarily those of the team.
The Cubs offered more money and he went to Chicago: as simple as that.
He went on to win the 2016 World Series with the Cubs and was part of another unforgettable playoff run.
You could surely ask Lester and he would tell you he has no regrets about his decision.
Something similar can happen with Bogaerts.