The Boston Red Sox have become among the most aggressive teams of the offseason, pursuing perhaps the two most prominent free agents on the market. General manager Ben Cherington appears to be in hot pursuit of former longtime Red Sox starting pitcher Jon Lester, San Francisco Giants third baseman Pablo Sandoval, and New York Yankees third baseman Chase Headley.

A source told ESPN’s Gordon Edes that the Red Sox have made an offer for Lester, who is expected to command a six-year deal over $100 million. However, no specifics of the offer have come to light. Lester’s agent said the Red Sox ownership showed “great respect” to the left-hander when they met earlier this week. Lester is reportedly expected to take his time deciding his next move, but a return to Boston five months after he was traded to Oakland was viewed as a strong possibility even at the time of the trade. The Red Sox drafted and groomed the star, and the team has the deep pockets to sign him despite talks previously breaking down over an extension. The Atlanta Braves may also be in the hunt to sign Lester.

Boston also is viewed as the biggest obstacle in San Francisco’s attempts to re-sign World Series hero Sandoval. ESPN also reported the Red Sox were expected to make an offer to the Venezuelan on Wednesday, but they might hesitate to offer a six-year deal given Sandoval’s fluctuating weight over the last five seasons. The Red Sox are considered the frontrunners for Sandoval.

Should a Sandoval deal fall apart, the Red Sox are expected to pursue Headley, though the Yankees are still in the mix, according to CBS Sports. It would be a provocative move for Boston to pursue a player who was on the Yankees, but it's certainly not unprecedented. Headley is expected to receive a deal worth far less than Sandoval.

Boston clearly intend to use their considerable salary-cap space to climb out of the AL East cellar, and they presently have far more dollars to throw around than the highest-spending teams in the Major Leagues.

According to Spotrac, the Red Sox are currently on the hook for $112.7 million in payroll for the 2015 season, the seventh-highest in the Majors and almost $79 million below the luxury tax threshold of $189 million.

The Giants aren’t too far ahead at No. 6 with $127.2 million tied to contracts for next season, but it does put them at a disadvantage as they try to keep their World Series-winning squad together. The Yankees owe $171 million next season, due to five players making more than $21 million, and they’ll have to fight Boston off for Headley. 

No. 5 on the list is the Detroit Tigers at $128 million. The Tigers could be in the market for a third baseman with Nick Castellanos finishing his first full season with a .259 average and 140 strikeouts, but again Boston has the space to outspend, especially with Detroit hoping to keep starting pitcher Max Scherzer.

The Philadelphia Phillies are No. 4 at $129 million, but the rebuilding squad is mired in long-term contracts like the Yankees are might hesitate to add another. There are also the two Los Angeles teams in the Dodgers (No. 1 at $212 million) and the Angels (No. 3 at $143 million) but neither has reported interest in Lester or Sandoval, or the perceived funds to chase them.

Boston certainly isn’t the default choice simply for monetary reasons. Beyond the history and tradition of Fenway Park, the Red Sox have won three World Series in the last 10 years and only the Giants can make the same claim.

And based off last year’s results, the case could be made that Boston was only a couple pieces away from contention.

The Red Sox have made the playoffs only once in the last five years, but adding Sandoval to a lineup that already includes Dustin Pedroia, David Ortiz, Yoenis Cespedes and youngster Xander Bogaerts could be enough to lift last year’s No. 18-ranked offense. Should the offense click again, run support won’t be a problem for Lester at the top of the rotation, followed up by a combined 28 quality starts from Clay Bucholz and John Lackey in 2014.