But only a few can offer robust packages in return.
Though he's coming off a frustrating year, Lester previously performed brilliantly in the always-competitive AL East. His durability has never been questioned (161 starts since 2008), nor has his courage. The left-hander was diagnosed with non-Hodgkin lymphoma in 2006, but he returned to the major leagues the next season after chemotherapy and rehab.
The two-time All-Star is owed about $11.6 million next summer, his age-29 season. His contract also includes a $13 million team option for 2014 that can be bought out for $250,000. Lester will be a bargain—even at those eight-figure amounts—if he regains his old form.
The following potential trade partners could provide considerable compensation for his services.
Former top prospect Brian Matusz still has great potential.
The Boston Red Sox aren't likely to do business with a division rival, especially one who dominated them last season.
Still, the Baltimore Orioles have players capable of meeting several needs.
Shortstop J.J. Hardy—signed through 2014—is available. The 30-year-old admitted in August that the presence of Manny Machado made him wonder about his future with the organization (via Dan Connolly, The Baltimore Sun). Hardy won a Gold Glove at the position a year ago and has averaged 22 home runs per 162 games in the majors.
Along with him, Baltimore could give the Red Sox a choice of a young pitcher or second position player.
Brian Matusz is a possible fit. He thrived in the bullpen during his team's surprising run to the playoffs, primarily seeing action in the seventh inning or later. However, the southpaw was groomed to be a starter and provided a 2.6 WAR in that role back in 2010, according to Baseball-Reference.com.
Or if Boston prefers another bat, how about Chris Davis? The slugger gained outfield experience at Buck Showalter's insistence. He would receive significant playing time on the Red Sox as Jonny Gomes' platoon partner and a fill-in for first baseman Mike Napoli (when he's being used behind the plate).
Asdrubal Cabrera would make the Boston Red Sox lineup even deeper.
The Boston Red Sox and Cleveland Indians have completed several prominent trades in recent years. The Victor Martinez-Justin Masterson blockbuster came together in 2009, and three years earlier, these teams exchanged seven players—including Coco Crisp—in a single deal.
After signing Mark Reynolds, the Tribe can finally focus on their thin rotation.
Cleveland peddled Asdrubal Cabrera aggressively at the winter meetings. Jon Paul Morosi and Ken Rosenthal of FOX Sports heard that the front office spoke with the Los Angeles Dodgers about acquiring shortstop Dee Gordon as his successor. With Jose Iglesias still unproven, Boston certainly wouldn't object to the $16.5 million remaining on Cabrera's contract.
The inclusion of left-hander David Huff seals this potential agreement. He has pitched in parts of four MLB seasons.
Outfielder Norichika Aoki had an excellent rookie season.
Tom Hardicourt of the Milwaukee Journal Sentinel writes that the Milwaukee Brewers aren't interested in offering three years to a starting pitcher. General manager Doug Melvin seeks an established arm, but will be hard-pressed to land one in free agency with that restriction.
Conveniently for the Brew Crew, Jon Lester is only guaranteed money through 2013.
Outfielder/first baseman Corey Hart probably won't waive his limited no-trade clause. CBS Sports' Jon Heyman tweets that he prefers teams that hold spring training in Arizona (the Boston Red Sox play in Florida).
No matter—Norichika Aoki makes more sense for Boston, anyway. He certainly shined in his debut season, starting at all three outfield positions and thriving as a situational hitter and baserunner. His .288/.355/.433 triple-slash line practically matches Jacoby Ellsbury's (.297/.349/.442), so the Red Sox would have an internal replacement in case their leadoff man—a Scott Boras client—leaves next winter.
Moreover, Milwaukee has a surplus of advanced pitching prospects. Melvin's interview on AM 1250 WSSP suggests that Wily Peralta and Mark Rogers are off limits, but either Johnny Hellweg or Tyler Thornburg would surely wet Boston's appetite.
Jameson Taillon should be contributing by September.
By expanding this trade, the Boston Red Sox can get a very special player.
Working with the financially-strapped Pittsburgh Pirates would mean eating at least half of Jon Lester's future salary. In addition, Boston must take in closer Joel Hanrahan, who Matt Swartz of MLB Trade Rumors predicts will earn $6.9 million through arbitration. The Pirates made him available to other teams earlier this month for that very reason, according to ESPN's Buster Olney (Insider access required).
Including standout reliever Junichi Tazawa may even convince GM Neil Huntington to part with outfielder Travis Snider, and more notably, former No. 2 overall draft pick Jameson Taillon.
The 21-year-old gets superb reviews from every scout. He's pitching with terrific control in the minor leagues and projected to begin next season at Double-A.
This move keeps the Red Sox relevant in the present and obviously positions them to contend for the rest of the decade.
Elvis Andrus is already one of baseball's elite shortstops.
The quality and depth the Texas Rangers have at shortstop is envied across the industry. If they don't use it to acquire Justin Upton, it will make the Boston Red Sox very happy.
This is the simplest trade proposal mentioned so far—Jon Lester for Elvis Andrus, straight up.
Andrus comes with a less expensive contract than Asdrubal Cabrera and affects a team in so many ways. He's an accomplished base-stealer and solid defender with good plate discipline and bat control. He also doesn't turn 25 until late August.
FanGraphs shows us that Lester has accounted for 26.0 WAR since reaching the big leagues in 2006. The only MLB pitchers ahead of him in that span needed more innings to do it.
Despite his outstanding performance in Boston, the left-hander isn't untouchable. The Red Sox will consider dealing him for the right package.