In December 2007, Randy Levine, president of the New York Yankees, helped re-sign third-baseman Alex Rodriguez to a ten-year contract worth $275 million, which was, and still is, the richest contract in the history of professional sports. For Levine, it was a giant bet, an Empire State Building–size stack of chips on the possibility that A-Rod, by consensus the best hitter and all-around player in baseball, would add to the Yankees’ bulging shelf of championships while mounting a serious campaign to break the home-run record. For Rodriguez, the contract was both a recognition of his immense talent and an outlandish promise to keep. It goes without saying that, over the course of a Yankees tenure that included two MVP years and a world championship, numerous slumps and streaks, and a pair of drug scandals that have come to define his career as much as his talent has, the men would have much to talk about, which they did primarily via e-mail. In the course of reporting the magazine’s December 9, 2013, cover story (“Chasing A-Rod”), I viewed a trove of the electronic correspondence between Rodriguez and Levine, a selection of which is excerpted below.

May 11, 2011

The Yankees lose to the Royals 4-3; Rodriguez, batting cleanup, collects just one hit in five at-bats.

Levine: Hey, tough game, I’m worried about your health, u sure u r ok? You look to me like you’re a little off. If just a slump, you will come out, but if more, let me know.

Rodriguez: Hey Randy, yes, tough game. Just a little jumpy at the plate. I feel fine. I’ve been working hard with Kevin Long [Yankees hitting coach]. I will start hitting soon. My team needs me. We will win tomorrow. Have a great night.

May 17, 2011

Rodriguez hits two home runs, leading the team to a win over Tampa Bay.

Levine: Way to go, welcome back … enjoy start of a roll.

Rodriguez: Yessir!! Our team needs me to hit and lead us.

Levine: U are the man. I told u that for years. U can and will do it.

October 2, 2011

The divisional series against Detroit is tied at one game apiece.

Levine: u r the leader … Keep confidence strong, get us home.

Two years earlier, Rodriguez had carried the Yankees through the World Series; against the Tigers, Rodriguez hits justs .111 and the Yankees lose the playoff series three games to two.

March 25, 2012

Rodriguez is hit by a pitch in a preseason game.

Levine: Ouch. Feel better.

Rodriguez: Can’t hurt me.

Levine: It hurt me watching.

Rodriguez: HA!

May 21, 2012

The Yanks are shut out by the Royals.

Levine: My friend, I have always believed that in difficult times there r two ways to go. The easy way, which is to make excuses, be defensive, or blame others and shut it down. The better way is to take the challenge, get mad, get determined, and shut everyone up and perform to greater levels. I believe in u. I believe u will hit those levels. It has been a tough year in injuries, tough losses, underperformance, but we need a leader, that is you. Take the lead, get these guys going, put a chip on your shoulder. When u succeed it will be Yankees lore. There is nothing more powerful than that. I am here to support u. Tell us what u need.

Rodriguez: You are 100% correct. This is no time for blame or excuses. Is time for me to be a leader and rally the troops. I feel if I perform at a high level, put a chip on my shoulder and lead the way, then my mates will follow my lead. Is not how you start, but how you finish. Let’s get it going tonight. Thanks for the support and stay in touch.

May 23, 2012

Rodriguez homers twice against the Royals in an 8-3 Yankees victory, Rodriguez’s first home runs in 52 at-bats.

Levine: Breakout game. Nice going. Chip on shoulder attitude. Get us on a roll.

July 30, 2012

Rodriguez is out with an injury, having fractured his hand five days earlier when hit by a pitch. Levine makes a reference to performance-enhancing drugs that he later refers to as a “bad joke.”

Levine: How r u feeing since u left Robby [Cano] under 200, he needs some steroids fast!

August 21, 2012

With A-Rod still out, Levine again makes a possibly comic drug reference.

Levine: Hey, what’s up with Robby. This guy must not be using the liquid. U didn’t tell me what did Chris and Steve say your ETA is. Don’t rush it unless u r right. We need you. Nova looks like he may need a breather. What do u see.

September 22, 2012

Rodriguez gets two key hits in a fourteen-inning victory that keeps the Yankees in first place. The chip on the shoulder the two have spoken about has become a nickname: Chip.

Levine: Way to go best win of year. U had walkoff mesa nerves. U stepped up do it tomorrow. Chip. Proud of u.

Rodriguez: Huge win. … Very nervous. Need to win tomorrow. Chip

Levine: That’s what leaders do.

That fall, the Yankees win their division, but Rodriguez has another terrible postseason, managing just a single hit in the championship series against Detroit, in which they are swept. In early December, Rodriguez is diagnosed with a torn labrum—a left-hip injury. Even the Yankees seem relieved. Says general manager Brian Cashman, “The struggles we saw in September and October are more likely than not related to [the injury].”

At home in Miami, Rodriguez begins “prehabbing,” building strength before the surgery, which is scheduled for January.

December 7, 2012

Levine: Pictures of party at your house circulating all around tonight … Guys in rehab don’t do this. This is not the sedate, small party you […] said. You need to focus on getting better.

Rodriguez: Been prehabbing every day. Pete [Draovitch, a trainer] arrives in Miami tomorrow. Is nice to disconnect a bit in the off season. But I understand your point. Really looking forward to getting mended.

Levine: Just looking out for you.

January 29, 2013

The Miami New Times publishes a story accusing Rodriguez and other Major League ballplayers of using banned substances provided by Florida-based anti-aging clinic Biogenesis. Rodriguez denies the charges. Publicly, the Yankees stay neutral, insisting they will wait for the outcome of Major League Baseball’s investigation. But there are constant rumors that the Yankees are rooting for his injuries to force him into retirement. In one call, Dr. Bryan Kelly tells Rodriguez what he claims Levine had said: “Levine told me the Yankees would rather Alex never step on the baseball field [again],” says a person who overhears a conversation. Levine can’t recall the conversation with Kelly, as he tells one colleague, but believes that he “might” have used words to the following effect: “Alex, this is your health, this is your life, if you choose to get off the field because you don’t want to be disabled, we’re fine with that.” Rodriguez decides to have the surgery.

February 28, 2013

Rodriguez: Randy, […] As you can imagine, I’m feeling left out, I can’t be with the team at spring training and this leaves an empty hole in my life. And on top of that I’m dealing with the backlash of all these ugly rumors and false stories. […] Of course I am very concerned about these rumors and about what the team is doing and saying about me. … People have been telling me that you have an 8% bounty on my contract.[…] Maybe all of this is coming from my cousin […], who knows. He claims he met with the Yankees and that you are after me and it has me concerned. I hope this [e-mail] is the start of us clearing the air between us. I don’t want us to be enemies. I am loyal to the team. I only want the best for the Yankees organization. But I do need reassurance from you and I need to know what is going on. It is bad business for everyone.

Levine: First off, neither I nor anyone at Yankees every met with your cousin. This is being handled by MLB and we r allowing them to do their job. There is no bounty on you. We have no idea who MLB is meeting with or what course their investigation is taking. It is entirely in their hands. We r not talking to the media on this issue, we have said this is being handled by MLB, and we will have no comment until the investigation is over. That’s it. There is nothing else going on. I wish u health and a good rehab.

In the summer, Rodriguez says he is ready to rejoin the team. In the past, that had prompted pep talks and cheers from Levine. Now Levine appears preoccupied by legal maneuverings. The nicknames are a thing of the past. Instead, he refers to his star as “Al.”

July 3, 2013

Levine: Hey Al, glad ur on ur way back. Quick question: some lawyer named James McCaroll [one of Rodriguez’s lawyers] keeps calling Hal [Steinbrenner, co-chair and managing general partner of the Yankees], says he is your lawyer, wants to talk about your investments. I called him. He is not taking my calls. Is he your guy? If so, have him call me. If not, you should have someone shut him down.

Rodriguez: Thanks for the good wishes. I’m focusing 100% of my energy on health, baseball, and returning to help us win. I will talk to Jim.

With Levine and Rodriguez barely speaking, the star and his team duel through the media.

August 3, 2013

Rodriguez: Can u please stop!! I want to play baseball and I could make a big difference to the game. Steinbrenner would roll in his grave IF he knew what was happening! Stop, Randy, this isn’t going to be good for any of us!! You are a businessman and what you are doing is ruining the business of baseball. If u want to meet in person to discuss it, let’s do it!

August 5, 2013

Levine: I received your email, the contents of which are a complete shock to me. As I have repeatedly told you, this is an MLB investigation. We had no role in initiating the investigation or assisting in the direction of the investigation. Despite your continued false accusations (which you know are false) we have acted consistently. My focus and direction, as well as that of the entire Yankees organization, has been, and continues to be, to treat you in the same manner as we do all of our players, to have you healthy and ready to play as soon as possible. Good luck.

That day, MLB announces a record 211-game suspension of Rodriguez. Because Rodriguez plans to appeal, he is permitted to continue playing. A couple of hours later, Rodriguez takes his first at-bat of 2013, blooping a single, his only hit in four at-bats in the Yankees’ loss to the White Sox. Levine’s is the last e-mail between them.

E-mail: Steve.Fishman@nymag.com.