The biggest question going into the Yankees' off-season was whether or not Judge would be back in pinstripes.
After the Astros swept the Yankees in the playoffs, Judge's manager and teammates hoped that his time in the Bronx was not over.
Roger Maris' American League single-season record of 62 home runs had stood for 61 years. I admire and respect someone that I have grown close to. Hopefully, we'll see him in pinstripes for a while. I don't want to think about the alternatives.
DJ LeMahieu, who missed the entire playoffs due to a foot injury, said he would be disappointed if he didn't return. You don't know how that works. He definitely wants to be here but when it becomes a business, it changes a lot.
Judge will be one of the biggest names available in free agency after declining a seven-year contract from the Yankees that would have made him the highest-paid baseball player in history.
The All-Star outfielder went on to have a career year in which he led all of baseball in almost every offensive category and surpassed Yankees legends like Babe Ruth and Roger Maris in becoming the new American League home run king.
In the aftermath of the Astros' sweep of the Yankees, Judge said he had not thought about his free agency or his future in pinstripes.
All of that will run through my agent. Judge didn't think about the next step. We have enough time to figure it out.
After the conclusion of the World Series, Judge was asked if he had talked to his teammates about advice on his upcoming free agency.
Judge spoke wistfully when he described his six-year career in pinstripes.
He said he didn't take for granted the honor of playing right field at Yankee Stadium. When I said a prayer, I would look around the stadium to see if there were any players that could play in front of the fans. The time was special. I don't like that they didn't bring home the title.
When talking about the gap between the Yankees and Astros, Judge made a small slip of the tongue. The Yankees lost to Houston three times in the last six league championship series and Judge referred to them as "we".
When we get there and secure this thing, it will make it a lot sweeter, going through the tough times, that's for sure," Judge said.
Judge reiterated his status as a free agent despite his desire to continue wearing the Yankee uniform.
Since I first wore the pinstripes, I have been clear about that. He said that they couldn't get something done before the season started. I'm no longer employed. We're going to see what happens.