The acceleration of Judge’s end game began on Dec. 5, when Trea Turner
ignited the winter meetings by rejecting the Padres in favor of an 11-year, $300 million contract with the Phillies
. That night, Judge attended the Monday Night Football game
in Tampa, chatting up Tom Brady
. He originally planned to fly home to Northern California the next day, then head to Maui with Samantha the following morning to celebrate the one-year anniversary of their wedding in Hawaii
The Padres had other ideas.
After losing Turner, they pivoted to Judge, believing it was a longshot but worth a try, considering Judge was one of the game’s biggest stars. Odle and Matranga initially did not know what to make of the Padres’ sudden interest, but quickly ascertained San Diego was serious and conveyed that to Judge. The agents also told the Padres that for the talks to move forward, a face-to-face meeting between Judge and team officials was necessary. Yes, even with the Judges on their way to Maui.
The Padres paid for a private jet; there are no direct flights from Tampa to San Diego. The Judge contingent — Aaron, Samantha and Penny, the miniature dachshund
— arrived in the late afternoon. Judge requested his agents bring him an order from In-N-Out Burger. The group then headed straight for Petco Park, not far from where the winter meetings were taking place.
The parties met secretly for about three hours at Petco, while a PSI assistant watched over Penny at the agency’s hotel. Judge toured the Padres’ clubhouse, their weight room, their batting cages. He asked questions. Samantha also spoke. The Padres’ contingent, which included owner Peter Seidler, general manager A.J. Preller, assistant GM Josh Stein and manager Bob Melvin, was thoroughly impressed.
Some of the Padres’ people left the meeting convinced Judge was leaving New York, and that his decision would come down to San Diego or San Francisco.
Preller wasn’t so sure.
“I thought the meeting went well,” Preller said. “But that evening, he flew out.”
The Padres do not believe Judge used them. His camp kept their visit confidential, and it only became public after he agreed with the Yankees. Preller, though, felt somewhat like a car salesman watching a shopper walk out of his showroom without completing a deal. If Judge truly wanted to join the Padres, wouldn’t he have stayed?
Perhaps, but Judge was telling the truth: He needed to get back to Northern California, the starting point for his vacation. Odle and Matranga tried to find him an alternate flight from San Diego to Maui in first class; Judge, at 6-foot-7 and 282 pounds, is too big to fly coach. No such flight was available, however, preventing Judge from staying another night.
So, the Judges kept their private flight to Stockton, only to see it hit a snag. The meeting with the Padres lasted so long, the pilots timed out. Odle and Matranga engaged in a mad scramble to find another plane. They finally located a small one, barely big enough to fit Judge, that would fly from Van Nuys to San Diego, then take the Judges to Stockton.
At around 9 p.m. PT, before leaving San Diego, Judge spoke with Yankees manager Aaron Boone, who was at the winter meetings and had just returned from dinner with several of the team’s scouts. The mood at the dinner was somber. The uncertainty over Judge had everyone on edge. At the end of the meal, Boone asked the scouts if he should reach out to Judge. Without hesitation, the scouts said yes.
The two connected. Boone asked Judge where he was with his decision, reaffirmed to Judge how he and the Yankees felt about him. He ended the conversation by saying, “Whatever you do, Aaron, don’t do anything without calling Hal.”
Little did Boone know, Steinbrenner would be the one contacting Judge.
At that point, Judge said, the Yankees were “not close” with their offer. Odle and Matranga, unaware Steinbrenner was about to re-enter the picture, were planning to resume conversations with the Padres and Giants the next day.
One Giants person said he was cautiously optimistic about his team’s chances, emphasizing the word cautiously
. A number of officials with the Giants and Padres, however, remained skeptical Judge would change teams. And sure enough, before boarding his flight to Stockton, Judge told his agents he had reached a conclusion: He wanted to stay in New York. He had unfinished business with the Yankees, who have not won a World Series since 2009.
A few hours later, Steinbrenner sent his fateful text. Their discussion took place at about 3 a.m. PT. Steinbrenner agreed to give Judge a ninth guaranteed year at $40 million. Then, after the two agreed to terms, Steinbrenner went one step further. He said he wanted to make Judge the Yankees’ captain.
It was over. Judge had taken less money to stay with the Yankees. Later, he would joke with Odle and Matranga, “we probably could have gotten this done in two phone calls” — meaning, just him and Steinbrenner. But he knew his agents played a larger role, guiding him to free agency rather than pushing him to sign an early extension, then helping him play out the process on the open market.
“Most of all, they were just a good sounding board,” Judge said. “I would say, ‘Here are some pros and cons I got on this. What did you think of that? What will this team look like in five years?’”
They talked. They strategized. They achieved maximum leverage.
“It came down to what I really wanted to do,” Judge said. “We made the right decision.”