I'm On a Boat
July 15, 2020

Jon Lester seen cruising the Chicago River in his boat “Lefthander,” Cubs by a million

Jon Lester is kind of a dick. That might sound a little harsh, but we actually think the Cubs southpaw would appreciate the honesty. The guy knows who he is. He keeps his friends close and his enemies closer, and he’s made plenty of the latter over the years. But after overstaying his welcome in Boston—arguably the grumpiest, meanest, most egomaniacal town in America—Lester has stuck in Chicago, the unofficial home of Midwestern friendliness and pizza cake. Why? Well, a World Series ring certainly helps. How? We have no idea, but there’s no doubt that he looked right at home on Tuesday, cruising the nautical byways of the Windy City in his yacht “Lefthander.” Folks, if you haven’t bet your house on the Cubs this season, run don’t walk.

Click right for video.

Kids, this is what “dialed in” looks like. We’re eight days out from baseball, and this dude is gut tanning on a boat in downtown Chicago. Speaking of which . . .

Never gets old, does it? If you’re wondering how Lester could be cooler than a cucumber in Lake Michigan in January days away from the start of the most uncertain MLB season since World War II, perhaps this will help to explain it.

Something tells us Lefthander isn’t the only galleon in Lester’s armada.