Jon Lester knows Anthony Rizzo’s free-agency challenge: ‘Grass isn’t always greener’

Anthony Rizzo appears to be a fan favorite in The Bronx already, but he might not be calling it home for long.

The first baseman in the last season of the seven-year, $41 million contract he signed with the Cubs in 2013.

Jon Lester – Rizzo’s old teammate on the Cubs – went through a similar situation in 2014. When Lester was on the Red Sox, the pitcher was traded to the A’s in the final season of his contract.

Many expected Lester to re-sign with the Red Sox, but he ultimately decided to join the Cubs.

“Everything happens for a reason,” Lester told WEEI. “Maybe [Rizzo] sees the grass isn’t greener and he wants to come back [to the Cubs]. Maybe he sees something else and wants to play the free-agent [game]. I’m excited for him. That weight on his shoulders has hopefully been lifted. He can just go play and not worry about anything.

“Sometimes you have to kind of hit reset and start over. It sucks. But with the ebbs and flows of our game, it happens and you just have to roll with it.”

Anthony Rizzo in his Yankee Stadium debut on Aug. 2, 2021. Jason Szenes for the New York Po

Rizzo joined Joe DiMaggio as the only players with five or more runs scored and two or more RBIs in their first two games with the Yankees. The 31-year-old went deep Friday and Saturday and tied Sunday’s game with a crucial hit. He received a standing ovation before his first at-bat in the Yankees’ 7-1 loss to the Orioles on Monday night in his Yankee Stadium debut.

Lester eventually signed a six-year, $155 million contract with the Cubs, where he won a World Series in 2016.

“That probably was the best thing that ever happened,” Lester said. “Because if we don’t come to an agreement — and then I go into free agency without knowing if I can play somewhere else — I may have taken the safe bet and stayed there.”

Anthony Rizzo and Jon Lester during their time with the Cubs. AP

“I was very fortunate that I got to be a part of a great organization for a long time. And then I got to pick another great organization. I got the best of a lot of worlds.”

The Yankees added Rizzo to balance their lineup with a left-handed bat who excels defensively, as well. The three-time All-Star and four-time Gold Glove winner is now the starter over Luke Voit – who has played just 29 of 104 games this season due to injuries.

However, with Voit still in the fold, nothing beyond this year is guaranteed. Rizzo will have options in the offseason – he can return to the Cubs, re-sign with the Yankees or test the open market.

“Maybe it works out to where he does come back to Chicago and this is a two-month stint [in New York],” Lester said. “We don’t know what the future holds.”