Red Sox Blockbuster Reunions with Jon Lester, Hanley Ramirez a Real Possibility

In their attempt to return to glory, the Boston Red Sox are flirting with the past. 

A little more than a year removed from their last World Series title, the Red Sox are again trying to fill huge gaps in their roster. The team is in need of a starting pitcher, a third baseman and some power in the middle of the lineup, preferably of the left-handed variety.

General manager Ben Cherington has a strong recent history with free-agent pitcher Jon Lester, who was the ace in Boston’s 2013 World Series run. He also has a long history with Hanley Ramirez, one of the more potent free-agent bats on the market, having known him since the Red Sox signed him in 2000 as a 16-year-old Dominican prospect.

Landing both players could shift some of the power in the American League East toward the Red Sox while reuniting them with players from their past.

"

So the #RedSox are interested in former Red Sox Justin Masterson, Hanley Ramirez & Jon Lester? Bring them all back!

— Off-season Mode (@TheRichSady) November 11, 2014"

While that sounds like a good storyline in Boston, going after both players on the open market is less plausible in reality.

The interest in Lester is real and warranted. The Red Sox knew the day they traded him to Oakland last July they wanted him back. A reunion was always possible, and Lester has never balked at the idea.

As the Red Sox rebuild, Lester would again nestle nicely into their rotation. Cherington knows Lester fits into his clubhouse and he is willing to hand over the years and $160 million or so it would take to lure Lester back to Beantown. 

That is the easy part. The hard part about landing the left-hander is having so much competition, which includes as many as five other teams. Although longtime baseball writer/analyst Peter Gammons believes some thinking around the league has Lester returning to Boston, we all know none of this speculation is the final word.

The Red Sox want Lester, but failed missions are often filled with a whole lot of “want.”

“Starting pitching is something we have to address,” Cherington told reporters last week at the GM meetings, according to Peter Abraham of The Boston Globe. “I’ve been saying that for a while now.”

Carlos Osorio/Associated Press

While Lester is the obvious top target on the pitching front for the Red Sox, Ramirez is not their primary target on the other side.

Free-agent third baseman Pablo Sandoval is the guy the Red Sox are going “all in” on, reported ESPNBoston.com Red Sox writer Gordon Edes. This makes a ton of sense since Sandoval would fulfill all of the lineup needs the Red Sox have, assuming he can hit for a bit more power in Fenway Park as opposed to the pitcher-friendly AT&T Park in San Francisco, his home for the previous seven seasons.

Sandoval, 28, flew to Boston to meet with Cherington and Co. on Tuesday, and the Red Sox will fawn over him until he signs elsewhere, if he does.

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Pablo Sandoval @KFP48 "excited" to be in Boston to meet with @RedSox pic.twitter.com/nLXUOgIeKe

— Joe Amorosino (@joeamorosino) November 17, 2014"

That locks Ramirez out of Boston for now, at least as a serious option. The Red Sox may still entertain the thought of a reunion with Ramirez while waiting for a Sandoval decision, but a few other dominoes have to fall perfectly in order for Ramirez to land there.

First, Sandoval has to sign elsewhere. Second, the Red Sox have to decide that a cheaper Chase Headley, while offering better defense, is not as good a fit as Ramirez, who is better offensively but a defensive liability and much more expensive. Regardless of how the Sandoval situation plays out and affects Ramirez’s market, he will still be seeking well north of $100 million for his first free-agent deal.

Other things have to happen for the Red Sox to commit to Ramirez, who will turn 31 next month. The Mariners have to pass on him in favor of Nelson Cruz or possibly a Matt Kemp trade, and it still has to be proven the Toronto Blue Jays and Houston Astros are only browsing in the Ramirez aisle.

Even if all those things happen, which they very well may, the Red Sox still have to decide whether Ramirez is a good fit for them. Even though he hits from the right side and is a shaky defender, Ramirez is an elite offensive player when healthy.

David Zalubowski/Associated Press

As CSN New England Red Sox insider Sean McAdam points out, Ramirez’s health is only one of a handful of concerns the Red Sox should have. Others include offensive decline, attitude and his willingness to change positions. Those are all legitimate, but if the Red Sox find themselves out of the Pablo Sandoval bidding soon, the concerns can be understandably overlooked.

Ramirez as a second option, along with a Lester signing, will still make the Red Sox a serious threat in their division.

The Red Sox have the money, front-office smarts and allure to smartly buy their way back into American League contention. Lester should be a part of that and Cherington knows it. Ramirez, who would have his career come full circle with a Red Sox reunion, is the uncertainty and not the team’s best option for that need.

Reunions aren’t always wonderful. If the Red Sox can do this thing by doubling back on only Lester, they will be better off. If they have to reach for Ramirez, it won’t be a total disappointment, but it will mean they didn’t land exactly what they desired.

This winter, Lester and Sandoval hold Boston’s cards.

Anthony Witrado covers Major League Baseball for Bleacher Report. He spent the previous three seasons as the national baseball columnist at Sporting News, and four years before that as the Brewers beat writer for the Milwaukee Journal Sentinel. Follow Anthony on Twitter @awitrado and talk baseball here.