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Tribune News Service
Tribune News Service
James O'Connell

Inside Aaron Judge’s free agency process and how Hal Steinbrenner channeled his father’s ‘charm’

NEW YORK — One moment can change the course of history. For the Yankees, that proved to be true in their pursuit of re-signing Aaron Judge.

If not for the infamous late-night phone call — 3 a.m. PT — from Hal Steinbrenner in Italy to Judge in California, the Yankees could still be stuck on just 15 captains in franchise history as the possibility of the MVP taking his talents elsewhere was very real.

The Bombers had an eight-year offer on the table and with the San Francisco Giants and San Diego Padres in hot pursuit of the 2022 AL MVP, that wasn’t going to be enough.

“Yeah [I was prepared to leave if Steinbrenner didn’t offer a ninth year], that was really a big thing for me,” Judge told reporters after his introduction as the 16th Yankee captain. “I wanted to get that ninth year.

“All it really took was getting on the phone with Hal and him saying ‘all right, let’s do it, what’s the hold up here?’ Because there was some pretty good offers out there. It would’ve been a tough financial decision to turn down some things. Ultimately, it came down to hearing Hal say we want you here, if [that takes] nine years, here’s nine years.”

Judge — who slashed .311/.425/.686 while mashing an AL-record 62 home runs last season — confirmed that he had received more than one formal offer from other teams in his testing of the free-agent waters.

The Yankees’ owner was heavily involved in the negotiations to retain his franchise player. The pursuit involved multiple in-person meetings and phone calls where the message was relayed to Judge that in his opinion, he was not a free agent and there were no doubts that he would be a Yankee.

“I think it was on a Tuesday night and we [Judge] had a conversation,” Steinbrenner said. “I woke up the next morning and talked about a lot of the things we talked about [in our first meeting after the season].

“That’s when I told him, you’re not a free agent as far as I’m concerned, you’re a Yankee. We just need to do what we can do to make sure that stays the same.”

Steinbrenner started feeling a little uneasy about the negotiations after that phone call, despite having felt that the Yankees had communicated well, however, he just felt that something wasn’t going right — industry speculation at the winter meetings indicated that his intuition was correct.

That’s when he made the call to Judge directly to secure the deal from across the globe, dropping the hammer with a ninth guaranteed year totaling $360 million, the largest contract given out in Yankee history.

General manager Brian Cashman and Judge’s agent Page Odle were involved every step of the way in between the process. However, Cashman stated that this was the most involved he had ever seen Steinbrenner in negotiations and got a little reminder that Hal is the son of George with an attitude of refusing to be denied.

“George had a real charm about him and a real way that when he was in that recruiting mode that could connect and sell and I saw a lot of that with Hal Steinbrenner during this process,” Cashman said.

“From start to finish, I think he personalized it with Aaron, he engaged Aaron right out of the gate. We got knocked out the playoffs by Houston and the next morning Hal and I got on the phone with Aaron directly and Hal spoke to Aaron about how important it was that he was a Yankee.

“It reminded me a lot of how his dad went about business too.”

On the other end of this was manager Aaron Boone. After reports surfaced that “Arson Judge,” appeared to be heading to the Giants, a sort of panic settled in with the Yankees’ skipper as he immediately called Cashman who was told by Odle that the report was “bulls---.”

Boone asked a roundtable of Yankees’ brass if they thought it was a good idea for the manager to hop on the phone with Judge one last time which was answered with a resounding yes.

Aside from reiterating how much No. 99 means to the organization, Boone pleaded with Judge to give Steinbrenner a final call before he makes any drastic decisions as he knew the owner would not let him get away which proved to be true.

In the end, a legacy in pinstripes meant more to Judge than a potential $400 million offer from the Padres or an enticing offer to return close to home. Throughout the process, the captain knew where he wanted to be and where he thought he belonged.

“In my heart, I knew where I wanted to be,” Judge said. “I think going through this process was a valuable lesson and just see what organizations are about. It was a tough situation going through free agency.

“Ultimately, it gave me a clearer answer that I belong here in pinstripes and I need to finish my career here in New York.”

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