Dan shaughnessy

One aborted trade changed Jon Lester’s future

FORT MYERS, Fla. — Jon Lester had his moment in front of the Boston media after the first official workout for Red Sox pitchers and catchers Monday.

Everybody wanted to talk to Lester about going into the final year of his contract. Will he really take a hometown discount to stay in Boston? Does he want Clayton Kershaw money? Can he truthfully tell us he wants to finish his career with the Red Sox? How much will it bother him if he goes through the season without an extension?

All good questions and Lester gave good answers.


But I wanted to ask him about 10 years ago when the Sox included him in a monster deal that would have brought the one and only Alex Rodriguez to Boston in exchange for Manny Ramirez. The trade was made, but then killed by commissioner Bud Selig, and A-Rod wound up going to the Yankees.

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Lester was only two years out of high school at the time, and had a 6-10 record in 25 minor league games. His name was not included in many reports of the Red Sox-Rangers trade. But the Red Sox told the 20-year-old lefthander that he’d been traded.

“I don’t know if it was publicized, but I got a call from my agent that day and he said, ‘You were traded,’ ’’ Lester recalled. “That’s how I found out. He called me and said I’d been traded and I said, ‘OK,’ and then he called me back a week later and said, ‘You haven’t been traded.’

“So for a week, I thought I’d been traded to Texas. It was weird. Especially at that point in my career. I didn’t understand the business side of things.’’

There are several million “what would have been?’’ thoughts attached to the notion of A-Rod coming to the Red Sox and Ramirez going to the Rangers. It means the 2004 Sox season would have been a whole lot different. We never would have seen Ramirez win World Series MVP, and the Sox would have been the ones strapped with the shameful legacy of A-Rod.


Nomar Garciaparra would have been traded for Magglio Ordonez. There would have been no “Tessie,’’ no “Fever Pitch,’’ and no image of Ramirez diving and cutting off a Johnny Damon relay throw that was bound for the infield.

A-Rod and his purple lips would have set up house on the left side of the Fenway infield and we’d probably never have seen Orlando Cabrera, Edgar Renteria, Julio Lugo, or Stephen Drew. Cameron Diaz and Madonna would have come to Fenway Park. Biogenesis would have made deliveries to the Back Bay.

And Jon Lester would have pitched for the Texas Rangers.

The New York Post tracked down Larry Lucchino on the topic and asked him what he remembered about the deal that didn’t happen and Lucchino said, “It was how we could be so cavalier to include Jon Lester in anything.’’

Think of the things we would have missed had Selig approved the deal. We wouldn’t have seen Lester pitch a no-hitter at Fenway. We wouldn’t have witnessed his courageous/triumphant battle with cancer. We wouldn’t have seen him smother the Colorado Rockies in the clinching game of the 2007 World Series and we wouldn’t have seen him dominate the postseason for the 2013 world champion Red Sox.


Lester’s bumpy moments in Boston are well-documented. He was one of the chicken-and-beer perps of the 2011 collapse that drove Terry Francona and Theo Epstein out of town. He loathed Bobby Valentine and pouted through an abysmal (9-14, 4.82) season in 2012. But he turned it all around for pitching coach-turned-manager John Farrell in 2013 and comes into his contract year in perfect position to strike gold.

He is a 30-year-old power lefty, good for 32 starts, capable of dominating big league hitters. He’s at his best when it matters most and he’s a free agent at the end of this season . . . unless the Sox work out a contract extension.

“It is what it is right now,’’ Lester said in Belichickian fashion. “I’ve got one year left on my contract and I’m going to play it out. We haven’t sat down. I think there’s going to be a time and a place for that. I’ll let the guys I pay to do that handle that. If it gets done during spring training, great. If it goes into the season, we’ll just play it by ear and see what happens.’’

When Lester came to Boston for the annual baseball writers dinner in January, he said he’d take a hometown discount to stay with the Red Sox. It’s the kind of statement fans love and agents hate.

“I’m not going to go back on what I said,’’ Lester said Monday. “I said what I said from the heart. I mean it. We’ll see where it goes from there. We still got a long way to go.

“It’s going to be a tough process. That’s why I tell those guys, ‘Call me when you got something.’ I don’t want to hear about the day-to-day of it. I’ve got to worry about the field. I can’t worry about that other stuff. It will take care of itself.’’

He sounds nothing like Jacoby Ellsbury last year. Ellsbury never offered a hometown discount. His message was clear: I will go to the highest bidder. I will not tell the people of Boston that I want to finish my career with the Red Sox.

Lester has no problem saying he’d like to finish his career in Fenway.

“You guys have probably figured me out by now,” he said. “I usually don’t say things I don’t mean. I mean it. I want to stay here. This is all I’ve known.

“I don’t like change. I don’t like going to new places that I have to learn. If I had to go to Arizona right now and find my way around and meet new people and have new teammates, I can deal with three or four new teammates, but not a whole squad of ’em. That would be kind of tough for me. I meant what I said. There’s no getting around it. I want to stay here, I want to be here until the end and see this thing out.’’

Will he be OK pitching all season in the final year of a contract?

“I think the biggest thing you have to watch out for is getting too emotionally caught up in the process of a contract negotiation,” he said. “You hear guys talk about going into arbitration and you hear from your own team how bad you are. That’s their job. They have to prove to you that you’re worth less than you are and we have to prove we’re worth more than what we are.

“It’s a tedious process and I let those guys handle it. When it gets down to it, I’ll sit down with my family and make the decision, what’s right for us. And if it’s to stay here, which we would love to do, then that’s what it is, but if we get to another point, then we’ll cross that bridge when we get there.’’

Your move, John Henry.

Dan Shaughnessy is a Globe columnist. He can be reached at Follow him on Twitter @dan_shaughnessy.