LA JOLLA, Calif. -- There was little doubt in Adrian Gonzalez's mind that they were meant to be together, the skinny high school baseball player with the grand ambitions and the young woman whose affections he was determined to win.
He went to Eastlake High. Betzabe Perez went to nearby Bonita Vista High. In his spare time, he would drive from Eastlake to where her car was parked at Bonita Vista, just to drop off little notes he had scrawled.
"I had so much free time to think of things to do for Betsy,'' he said, "to get her to fall in love with me.''
Now graduation day was approaching, both schools holding their ceremonies the same day, and Gonzalez was looking to make a bold play, the kind he was unafraid to make on a baseball field. Other first basemen, you hit a ground ball their way with a runner on second, they'd take the sure out at first. That's not how Gonzalez approached the game. He'd scoop the ball up and fire it across the diamond, trying to catch the lead runner advancing to third.
Why play the game, he reasoned, if you were not willing to take chances. So he asked John Boggs, the agent he'd hired to advise him on his first professional contract, if he knew somebody who could help him execute his plan. "He might as well have asked me if I knew how to go spelunking,'' Boggs says now. This was beyond his normal reach. But he agreed to help.
Which is how it came to pass, on the day that Betsy was to receive her diploma from Bonita Vista, that excited classmates pointed skyward. A small plane circled overhead, pulling a banner behind.
"I love Betsy, #19,'' the banner read.
A flying start
Now, a full decade later, Adrian and Betsy Gonzalez are on another plane, one taking them to Boston with Boggs and his associate Tony Cabral, to negotiate a deal that would make him a member of the Red Sox. Also on the flight are Red Sox general manager Theo Epstein, who had come to San Diego to strike a deal with Padres GM Jed Hoyer, and special assistant Dave Finley, the native San Diegan and scout who had signed Gonzalez after his employer at the time, the Florida Marlins, drafted Gonzalez No. 1 overall in 2000.
Gonzalez's hometown team, lacking the financial resources to offer him the kind of contract extension commensurate with other players at his high level, like Phillies first baseman Ryan Howard or Twins catcher Joe Mauer, had elected to cut ties a full year ahead of free agency. The Padres had traded him to the Red Sox for three of Boston's top young prospects: pitcher Casey Kelly, first baseman Anthony Rizzo and center fielder Reymond Fuentes.
Now, Gonzalez and his representatives had 48 hours to come to terms with the Red Sox on a contract extension. Without one, the Red Sox, as much as they had coveted Gonzalez for years as the middle-of-the-order slugger they needed to complement, and ultimately succeed, David Ortiz, were unwilling to part with so much prime young talent.
The clock was ticking. Boggs and Cabral would do most of the dirty work, bringing in Gonzalez only near the end. Betsy had accompanied Adrian, who has never played at Fenway Park, for a sneak preview of what they expected would become their new baseball home.
The first night, in a party that included Red Sox owner John W. Henry, who had owned the Marlins when Gonzalez was drafted No. 1 overall in 2000, they all went out for Italian food at Ristorante Strega in the North End. By chance, Red Sox center fielder Jacoby Ellsbury was also there dining, and they exchanged greetings.
It was a convivial start to what Gonzalez had hoped would be a straightforward process. The next day, Saturday, Dec. 4, he went to Massachusetts General Hospital, where the Red Sox medical staff gave him a complete physical. Gonzalez, who had undergone surgery to repair a torn labrum in his right shoulder just seven weeks earlier, left the facility believing he had passed with flying colors.
So why, barely 24 hours later, did the player and his agents walk out of Yawkey Way convinced that they had reached a dead end with the Red Sox?
Contingencies, and more contingencies
It was a word they would hear over and over in the offices of the Red Sox, one that would leave them numbed by its intractability. Contingencies.
The Red Sox wanted Gonzalez. He wanted to play for the Red Sox. On that, the parties were agreed.
But the Red Sox wanted protection. The physical notwithstanding, they were acquiring damaged goods. It was not in dispute that Gonzalez, even though he was convinced he would fully recover from surgery, would not be able to swing a bat before March 1 at the earliest.
So, there were contingencies. The Red Sox did not want to do a deal unless they signed Gonzalez to an extension, but they were reluctant to negotiate an extension until they saw him healthy. Shoot, never mind the extension -- the Red Sox had some reservations about negotiating the trade itself, giving up the players and the cash while entertaining the risk, however small, that Gonzalez would not be the same player he was post-surgery.
At one point, Gonzalez said he was led to understand that if he failed a physical in spring training, he could be sent back to the Padres, and the Red Sox would get their prospects back. That wasn't the case, sources on both sides said, but it increased the anxiety.
"I understood where Boston was coming from -- they were getting rid of a lot, they wanted to make sure I was healthy,'' Gonzalez said. "But from my perspective, it was, like, seriously? Come to spring training with Boston, go through the whole thing and all of a sudden, 'Hey, you're no good to us because your shoulder's no good?''
All the uncertainty about doing the trade itself, or doing it only with lots of contingency language, left precious little time to negotiate an extension. If the Sox had so many reservations, the Gonzalez camp thought, why were they even there? Boston always had the option of revisiting the Padres in the spring, if it made them feel better, although waiting carried its own risk: What if San Diego got a better offer from another club in the meantime?
There were other risks the Red Sox would take in waiting on an extension, or doing the deal without having gotten agreement from Gonzalez on an extension. What if, in the interim, Cardinals slugger Albert Pujols, like Gonzalez eligible for free agency after 2011, signed an extension for $30 million-plus a season? Gonzalez could turn around and tell the Red Sox, sorry, but what would have gotten a deal done in December no longer holds water in April. The price has changed, and if you don't meet it, we'll just go out on the market after the season, and, by the way, sorry about your prospects.
The deadline to work out an extension arrived without an agreement. Gonzalez was a signed player for 2011 -- he had one season left at $6.3 million under his existing contract with the Padres -- but nothing else had been resolved. There was no signed piece of paper between the Red Sox and Padres, no terms of agreement sheet, no new uniform player contract addressing the years beyond '11.
The Gonzalez camp had its suspicions that there was another factor at play. If the Red Sox waited until after Opening Day to sign Gonzalez to an extension, it would not count against the 2011 payroll for competitive balance tax purposes (CBT), better known as the luxury tax.
The agents, with Gonzalez in tow, rose to leave. They walked out onto Yawkey Way, hailed a cab and headed back to the Mandarin Oriental hotel. Boggs began checking flights to San Diego.
Matter of trust
It helped, in the end, that there was a strong comfort level among the two sides sitting across the table from each other.
Boggs knew Larry Lucchino during his Padres years, having represented San Diego's most beloved player, Tony Gwynn. He also knew Epstein since his early days with the Padres, and he and Gonzalez had come to know Henry when they originally signed with the Marlins. Finley had remained close to Gonzalez in the decade since signing him with Florida.
And in the end, what may have made a deal possible is that the Red Sox elected to take Adrian Gonzalez at his word, not an easy thing to do in an age where uber-agents and their clients rarely settle for less than the last dollar on the table.
Boggs and Gonzalez were discussing whether to take a connection back to San Diego that night or fly out the next morning when the phone rang in the hotel room. It was Epstein. The Sox had gotten another small window from the commissioner's office to keep talking. He and Lucchino were on their way over.
Gonzalez made his case as directly to the Red Sox as he had to Betzabe Perez all those years ago. Worried about his shoulder? He had played the entire season with it hurting. Multiple doctors had assured him that surgery would only make it better, he said, and in the off chance it didn't, well, he'd already figured out how to play in pain, as his 31 home runs, 101 RBIs and .298 batting average had proved.
As for the money?
"I made a comment to Theo, 'Make the trade happen by itself, and I promise you during the season I'll negotiate,''' Gonzalez said. "I'm not going to come here and be like, 'OK, we'll see you at free agency and see if you outbid the other teams.' We'll negotiate during the season. We're going to be fair. We won't be looking for record-breaking deals. We just want market value.
"We gave them our word that we were going to negotiate during the season in good faith. We're not going to go in there and ask for Albert Pujols' contract, something along those lines.''
Pujols' presence was clearly felt at the table. The Red Sox couldn't shake the notion that if Pujols signed a mega-deal, the shared parameters of what market value was could change overnight.
"That was one of their comments, what if he gets this humongous deal and you want to be closer to him?'' Gonzalez said. "I said, 'Trust me. What the market is today might change by then, but we're going to negotiate based on what the market is today.'''
No paper, but a promise
If Gonzalez could be taken at his word, Boggs and Epstein had reached a consensus on what it would take to get an extension done. Gonzalez was fully educated about the market, too: Fellow first baseman Howard, at 31 three years older than Gonzalez, had signed a five-year, $125 million extension with the Phillies that would begin in 2012. That's an average value of $25 million a year. Fellow left-handed batter Mauer, who like Gonzalez hits for power and average and at 27 is a year younger, had signed an eight-year, $184 million extension with the Twins, a smaller average annual value ($23 million) than Howard, but for more years.
The Red Sox were about to sign 29-year-old outfielder Carl Crawford to a seven-year, $142 million deal (AAV just over $20 million). Clearly, Gonzalez could expect a deal of similar duration, and for a higher AAV, in the $22 million to $23 million range.
That was a deal the Red Sox were willing to make, once they received further assurances Gonzalez was healthy and they could milk the CBT advantages. But could they trust Gonzalez?
This, admittedly, was the agent talking, but Boggs said he was willing to stake his reputation on these words: "Adrian is all about trust, honor and integrity,'' he said. "That's who he is as a person.''
As darkness fell late that Sunday afternoon, the Red Sox arrived at a similar conclusion. They had developed enough trust, one club source would say later, and shared enough information, that they decided to proceed with the deal.
The Red Sox and the agents informed all the other parties involved -- the Padres, the commissioner's office, the players' union -- that they had come to an agreement. There was nothing new in writing -- certainly no new contract -- and it's doubtful that a term sheet would even be binding, no explicit parameters in place. Just a mutual understanding and a shared conviction.
Yes, Adrian and Betsy Gonzalez would fly back to San Diego the next day. But now the whole world knew they'd be coming back to Boston. And they didn't need a banner to proclaim the news.
Gordon Edes covers the Red Sox for ESPNBoston.com. Follow him on Twitter.