Boston Red Sox Rumors: Jon Lester Could Head Back To Boston — Except For One Thing

Ever since the Boston Red Sox traded Jon Lester to the Oakland A’s on July 31, rumors have indicated that the ace left-hander would return to Boston for the 2015 season. Lester, whose 2014 season ended with Oakland’s dramatic Wild Card Game loss to the Kansas City Royals, now becomes a free agent and clearly fits the Boston need for a front-line starting pitcher.

Lester himself, shortly after arriving in Oakland, opened the door to the possibility of Red Sox return.

“At the end of the season, it’s not going to change my mind about going back there if they are aggressive and competitive and do the things they say they’re going to do,” Lester said. “Boston is definitely a place I would go.”

But there’s just one problem. Over the weekend, even before the A’s season officially came to an end, Lester put his $1.85 million home in Newton, Massachusetts — a well-to-do suburb just outside of Boston — on the real estate market.

So what does that mean for Red Sox fans? Is the real estate listing Lester’s way of telling Boston to abandon all hope of his return?

Possibly. But it could also be an acknowledgment by Lester that the Red Sox themselves may not have the 30-year-old, who between Boston and Oakland this year posted the best ERA of his nine-year career, at the top of their priority list.

The Red Sox clearly need starting pitching. Their opening day rotation in 2014 consisted of Lester, Jon Lackey, Felix Dubront, Jake Peavey and Clay Buchholz. But once Boston General Manager Ben Cherington was done with his trade deadline frenzy only Buchholz remained in a Red Sox uniform.

The Red Sox extracted righty Joe Kelly from the St. Louis Cardinals, but otherwise, they left three slots open in their starting rotation. A parade of young prospects, including Anthony Renaudo, Rubby De La Rosa and Allen Webster, auditioned for the roles throughout the final two months of the season.

But none of the youngsters left a strong impression. “They all did some good things, some not-so-good things,” said Cherington after the Red Sox season ended. “I think that they all are better for the experience.”

So why wouldn’t Cherington and the Red Sox pull out all the stops to re-sign Lester, who was picked by Boston in the second round of the 2002 draft by then-interim General Manager Mike Port?

Simple. There’s another 30-year-old lefty ace who is likely available. Of course, that would be the Philadelphia Phillies’ Cole Hamels, who is only 11 days older than Lester, was also taken in the 2002 draft, and made his big league debut just one month before Lester — and most importantly, has put up very similar numbers to Lester’s.

In fact, Hamels’ 2014 ERA of 2.46 was only slightly behind Lester’s 2.35, and was also the best of his career.

The difference? For the Red Sox, who have a strong aversion to long-term contracts, Hamels has just four years left on his contract at an average $22.5 million per year. Lester will almost certainly be seeking a minimum five-year deal on the free agent market at an annual value at least matching the Hamels deal.

The only disadvantage to the pursuit of Hamels for the Red Sox is that acquiring him would require giving up at least one top young player in trade, very possibly Mookie Betts, the most impressive of the Boston prospects to emerge in 2014. Lester, on the other hand, can be acquired without giving up any personnel.

With all of the rumors around the Red Sox offseason, one thing is certain — wherever he ends up, Jon Lester will definitely be able to afford a new house, in the Boston area or somewhere else.