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The Red Sox and A-Rod: What if?

They rank among the great what-might-have-been stories in Red Sox history.

What if an organization with a history of racial intolerance had given more than a sham tryout to Jackie Robinson or listened to the urgings of a scout named George Digby to sign a young outfielder named Willie Mays?

What if Red Sox owner Tom Yawkey had, in the cold light of morning, decided to follow through on the trade arranged over drinks the night before with Yankees co-owner Dan Topping, one in which the Sox would have swapped Ted Williams for Joe DiMaggio?

And what if the Red Sox had succeeded in their audacious effort 10 years ago to acquire Alex Rodriguez, generally acknowledged as the best player in the game at the time, from the Texas Rangers?

Ten years ago Monday, Rangers owner Tom Hicks declared that effort "totally, totally dead.'' He would soon send a letter to Rangers season-ticket holders pledging that Rodriguez would be the team's shortstop on Opening Day 2004. Then, on Valentine's Day, he traded him to George Steinbrenner's Yankees.

With A-Rod now shamed and a shell of his former self, a player who went from being championed by the game's ruling class to pariah, it is easy to regard Boston's failed courtship as a blessing, a disaster averted.

But that's with the benefit of hindsight. At the time, the Sox -- and A-Rod -- were bitterly disappointed that it did not come to pass, this deal first proposed by Hicks to the Red Sox within days of their crushing Game 7 loss to the New York Yankees in the 2003 ALCS.

Hicks was looking to get out from under the game's biggest contract, a $250 million, 10-year deal that in its first three years had not lifted the Rangers out of mediocrity. He asked for Nomar Garciaparra in return. The Sox countered by offering Manny Ramirez, whom they had placed on irrevocable waivers only weeks before without any takers.

With that deal in play, Red Sox GM Theo Epstein made another at the winter meetings, arranging to trade Garciaparra to the White Sox for slugging outfielder Magglio Ordonez. That second trade was contingent on the A-Rod deal being approved, but when Epstein entered the hotel room of his new manager, Terry Francona, and rattled off a prospective lineup that included Johnny Damon, A-Rod, David Ortiz and Ordonez, on knees made unsteady by multiple surgeries, Francona climbed onto his bed and did an impromptu dance.

That same night, Epstein slipped out of the meetings in New Orleans and flew to New York to meet with Rodriguez and his then-wife, Cynthia. Owner John W. Henry had already met with the couple in Miami, granted extraordinary permission to do so by commissioner Bud Selig, who had run into Rodriguez at Sammy Sosa's party in the Dominican Republic and listened to A-Rod earnestly express his desire to play for the Sox.

I was working for the Boston Globe at the time, and I, too, went to Miami to meet with Rodriguez. I liked him. He was smart, engaging and gracious. I believe he really wanted to play for the Sox. I had seen him when he'd made his major-league debut at Fenway as an 18-year-old from Miami, and I was impressed with his appreciation of Boston and what it would mean to his legacy if he would be the one who led the Sox to a World Series title after 86 years without one.

The deal was complicated and ultimately collapsed under its own weight. The Red Sox, for luxury tax reasons, wanted to reduce the value of Rodriguez's contract by $4 million a year, a total of $28 million over the remaining seven years of his deal. That was a nonstarter for the union. Any reduction, the union lawyers said, would require "added benefits" from the Red Sox -- like the Mets gave Mo Vaughn when they added two more teams to the no-trade provisions in his contract in exchange for a $500,000 reduction. The Sox tried to sell the union on an "added benefit" of allowing A-Rod the chance to opt out of his contract after two years and become a free agent, a proposal ridiculed by the union, which argued that A-Rod, because his contract was so much more than anyone else's, probably would have been looking at a pay cut. They made a counteroffer the Sox deemed unacceptable.

Hicks, meanwhile, was seeking some immediate financial help and not only wanted the Sox to assume A-Rod's contract, but pay a portion of Ramirez's deal so that he could pursue some pitching in free agency. That was not going to happen. But on his own, A-Rod contacted Hicks and offered to pay, out of his own pocket, the $15 million Hicks wanted from the Sox. That's how badly he wanted to come to Boston.

By the end of talks, there were bruised feelings on all sides. Henry was upset that Hicks had made little effort to keep negotiations quiet. Hicks was furious with Sox CEO Larry Lucchino, to the point that Tom Werner became the Sox point man with the Texas owner. Lucchino and union lawyer Gene Orza took whacks at each other. Garciaparra never recovered from the shock of learning that the Sox had sought A-Rod, even as Henry later explained he initially thought that they could have co-existed. And A-Rod resigned himself to remaining with the Rangers.

The upshot, of course, is that the Sox won two World Series in the next four seasons without A-Rod, and won their third in the 10 seasons in which Rodriguez has been a Yankee. And A-Rod alienated his longtime friend Derek Jeter, the first of many soap operas that would mark his time in New York. And then came the PED revelations.

That part of the story, sadly, would have been no different had he played for the Red Sox instead of the Yankees. But the rest of it? Ten years later, I still believe it could have gone a different way for A-Rod in Boston. Instead of a wary Jeter, he would have been embraced by David Ortiz, who remains one of his good friends in the game. He also was very close with Ordonez, who would have combined with A-Rod to more than compensate for the loss of right-handed power Ramirez represented.

He would have remained at short, where his value to the club would have been greater than it was to the Yankees at third.

In his first five seasons with the Yankees, through the 2008 season, Rodriguez hit 208 home runs. No one in baseball hit more. And Fenway is much kinder to right-handed hitters than Yankee Stadium. He was one of 10 players who had an on-base percentage greater than .400 in that time. He averaged 6.8 in WAR in that time.

Call me naïve, but I think Boston would have brought out the best in him, and he would have been loved for it.

We'll never know, of course. And in this town, I am well aware, that's hardly a popular thought. But there's a part of me that has never forgotten the shining promise of that 18-year-old and laments that it has ended the way it has.