That responsibility falls on Ben Tuliebitz, director of team travel and player services. He handles the team's road transportation -- buses, planes, hotels -- communicates between the clubhouse and front office, and maybe most importantly, he helps players with everything from ticket requests to real estate to finding pet sitters. Undoubtedly, late July into August is a busy time.
"It's busy, to say the least," said Tuliebitz. "Phones are ringing, the email is buzzing, the text messages are coming through. There's not a whole lot of sleep, but hopefully at the end of the day, if the team does well, you figure you can catch up on all your sleep after the postseason is over."
With each new face comes new preferences and new responsibilities, primarily fostering a welcoming environment in a place that can first appear intimidating. Acclimating players to the Yanks' clubhouse is a simple start. Helping them navigate New York City is slightly more challenging.
Ask Headley, who was acquired from the Padres on July 22 and lived in a Times Square hotel when he first arrived.
"Being right in the tourist center of the world is not what I am. ... I'm not a big city person," said Headley. "I've never been that."
Headley, a native of Fountain, Colo., has lived in the western half of the country nearly his whole life. Besides a brief stint at the University of Tennessee, he started his college career in California, and after getting drafted by the Padres, he spent time in the system's varying western locations. Until a few weeks ago, Headley's entire seven-year Major League career had been in San Diego.
"I'd like to get a little bit outside the city," said Headley, who wants to find a two- to three-month lease. "With my wife and 3-year-old son, I think they would be more comfortable. That's the goal, but we'll try to line up some places. It's different, but it's exciting, too. There's nothing like it."
Under the Collective Bargaining Agreement, the Yankees provide newcomers with seven days in a hotel and seven days of meal money, as if they were on a road trip. It eases their transition to the team and keeps the players from scrambling to find accommodations when they get the fateful call from general manager Brian Cashman.
"It's been smooth. Most of it has just been life stuff, just dealing with the city," said McCarthy, who spent significant time in Oakland and most recently Phoenix. "It's a different pace of life. New York City, I don't compare to anywhere else. That's just its own universe."
The families end up being the unsung heroes through this process. Take Headley's wife, Casey, who made several cross-country pit stops when her husband was traded, packing up clothes in San Diego and flying out to see him in Boston shortly after switching clubs.
"She's a trooper," said Headley. "We kind of knew. We had a pretty good idea something was going to happen, so we were prepared for it. She's making it as easy as possible."
Brandon McCarthy's wife, Amanda, who has been vocal on Twitter regarding the transition into New York, recently found an apartment, but she is still struggling to get to the Stadium. She and Brandon have tasted the rigors of New York City traffic and the trials of public transportation.
"That's been a hiccup for both of us," said McCarthy, who doesn't have a car with him. "But we'll get it sorted out, and you realize we'll just leave earlier, maybe get somewhere earlier if the traffic happens to be nice that day. It's just finding anything I can at this point, where it's just taxis or subway. Getting here somehow is basically the goal."
"They also lean on their older teammates, guys who are here," said Tuliebitz. "Some players want to immerse themselves in the culture in New York. They want to eat at the best restaurants, they want to go see a show, that when they're not playing ball, they want to take advantage of New York City. Every player is different in the way they approach it."
Drew's arrival to the Yankees made life much easier for Tuliebitz considering he was acquired while the Yanks were in Boston. Drew and Kelly Johnson swapped clubhouses, similar to when Ichiro Suzuki was traded while New York was visiting Seattle. Drew and Johnson have even considered swapping their apartments for the time being.
"I haven't gotten settled, to be honest. We're still trying to find a place," said Drew, who is looking for a house in Westchester County. "It's definitely an adjustment, trying to get my kids settled and everything else. It's kind of been a whirlwind. I am finally looking forward to finally getting my family settled, trying to get my boys and life settled. It'll be a lot easier then."
With the Red Sox in 2013, Drew got accustomed to the pace of the East Coast. But the switch for McCarthy might take some adjusting come football season, when, as he claims, the time difference will prevent him from watching morning NFL games to check his fantasy team.
As for Headley, a colder September might breed nostalgia for San Diego's postcard weather. But after seven years in Southern California, Headley seems ready to trade that in for nastier conditions if it means playing in October.
"As much as everyone wants to talk about how nice it is [in San Diego], I almost got tired of it sometimes," said Headley. "Man, I want a season here and there."