Jon Lester Shares Advice For Anthony Rizzo After Cubs-Yankees Trade

Jon Lester has walked a mile in Anthony Rizzo’s shoes.

So, it’s only fitting the former teammates spoke before and after the New York Yankees acquired Rizzo from the Chicago Cubs last Thursday, one day prior to the Major League Baseball trade deadline.

But what exactly did Lester say to Rizzo, whom he first met during their time together in the Boston Red Sox organization before reuniting several years later in Chicago?

Well, the 37-year-old pitcher apparently offered some advice based on his own big league experience.

“I was very fortunate that I got to be a part of a great organization for a long time,” Lester said, according to The Athletic’s Patrick Mooney, referring to his time with the Red Sox. “And then I got to pick another great organization. I got the best of a lot of worlds. Obviously, Rizz and I talked a lot more recently. But I told Rizz that when I was there with the Cubs, ‘Hey, man, the grass ain’t always greener, but sometimes it is.’ He’ll find that out. Maybe it works out to where he does come back to Chicago and this is a two-month stint (in New York). We don’t know what the future holds.”

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Lester, drafted by the Red Sox in 2002, spent parts of nine major league seasons with Boston, winning two World Series titles, before being shipped to the Oakland Athletics at the MLB trade deadline in 2014. He then signed with the Cubs during the ensuing offseason and spent six seasons alongside Rizzo in the Windy City.

Rizzo, drafted by the Red Sox in 2007, had been traded twice before last week — in December 2010 to the San Diego Padres and in January 2012 to the Cubs — but Chicago had become home for the 31-year-old first baseman. He spent parts of 10 seasons with the Cubs, notably winning a title in 2016.

It’s certainly possible, although perhaps unlikely, that Rizzo returns to Chicago this offseason. After all, Lester considered signing back with Boston in free agency before the 2015 season.

It might all depend on how Rizzo adjusts to life outside of Wrigley Field. He could embrace the change, much like Lester ultimately did despite his love for Boston. Or he could decide Chicago is where his heart resides. We just don’t know.

“That probably was the best thing that ever happened,” Lester told Mooney, referring to the 2014 trade that sent him to Oakland before he later signed with Chicago. “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. Like I said, everything happens for a reason. Maybe (Rizzo) sees the grass isn’t greener and he wants to come back. 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.”

Lester, traded last week to the St. Louis Cardinals after a 16-start run with the Washington Nationals, is at a different point in his career than Rizzo, whose arrival in the Bronx already is paying dividends for the Yankees. But he’s certainly someone Rizzo can turn to for advice as he navigates the unknown.