'Mystery' Dodgers Flexing Their Resources with Last-Minute Push for Jon Lester

Right on cue, here come the big, bad Los Angeles Dodgers, swagger in tow and checkbook in hand.

The Dodgers had been a team dismissed in the rumors swirling around Jon Lester. But just as the field seemed to be narrowed to a trio of clubs—the Boston Red Sox, Chicago Cubs and San Francisco Giants—the new front-office regime in Hollywood has locked in on the free-agent ace left-hander, according to a report late Wednesday night by Alex Speier and Rob Bradford of Boston’s WEEI.com.

A report earlier in the day by CSN New England’s Sean McAdam had Lester ready to decide between the other three teams by the end of the week and before the winter meetings start Sunday. That likelihood barred a late entrant into the bidding.

Enter the Dodgers.

"

Multiple sources tell .@bradfo and me that Dodgers are showing serious interest as late entrant in Jon Lester derby http://t.co/iuKdnoHWdr

— Alex Speier (@alexspeier) December 4, 2014"

According to WEEI sources, the Dodgers have already made an offer to Lester, which is likely to be more than the reported $130 million from the Red Sox and $138 million from the Cubs. Earlier in the day, ESPN.com’s Jayson Stark and Mark Saxon learned that a fourth team was in on Lester, but the Dodgers were never mentioned.

The development should not be completely surprising; the Dodgers still have that seemingly never-ending waterfall of cash falling onto their heads. While Lester doesn’t meet one of their more pressing needs—clearing the logjam of outfielders, finding a shortstop, finding a catcher and fixing a flawed bullpen—he is the kind of acquisition that could make the club clear favorites in the National League West, if not the entire National League.

Plus, there is the major added bonus that it would keep Lester away from the rival Giants, who courted the pitcher in Atlanta earlier this week.

Another reason why you need not be surprised by the Dodgers’ sudden inclusion in the fight for Lester is that the team’s new general manager, Farhan Zaidi, laid the groundwork for something big last week. Also, Zaidi was instrumental in the Oakland A’s trading for Lester last July while he was still the assistant GM there.

"Having that base of depth gives you the opportunity to make more aggressive, needle-moving moves as the offseason goes on," Zaidi told Eric Stephen of True Blue LA while discussing the team’s minor moves. "While we're weighing some of those bigger potential decisions, adding depth is going to be a constant focus for us."

Damian Dovarganes/Associated Press

Signing Lester to a nine-figure contract would fulfill both the bigger decision and the adding of depth without costing them a draft pick since Lester was traded from Boston to Oakland midseason. The Dodgers are in the market for a fourth or fifth starter with Clayton Kershaw, Zack Greinke, Hyun-Jin Ryu and Dan Haren occupying the other spots in the rotation. While they could have been frugal to fill the spot, going this big could be an attempt to mask other deficiencies, such as shortstop and the bullpen.

The move also makes sense considering Greinke can opt out of his six-year, $147 million contract after next season. While next season’s crop of free-agent pitchers figures to be impressive—David Price, Jordan Zimmermann and Doug Fister are among the group—Lester could turn next year’s Dodgers rotation into one of the most impressive units in recent memory with three legitimate aces heading it.

Plus, if Greinke decides he can get more money from the Dodgers or elsewhere next offseason, L.A. can still go out and snag one of the other front-line pitchers on the market in 2015.

As far as adding payroll, well, the Dodgers would have liked to get their arms around it some going into next season, but they obviously smelled an opportunity with Lester. One of the WEEI sources said he would be "shocked" if the Dodgers did not have the highest bid.

While this would be a massive, league-shifting deal if the Dodgers pull it off, they still have a big problem in their outfield, and signing Lester cannot solve that. The team has six outfielders for three spots, although it is known that Scott Van Slyke will be relegated to a right-handed power bat off the bench. The others—Matt Kemp, Carl Crawford, Andre Ethier, Yasiel Puig and Joc Pederson—all want to start, and aside from Pederson are all making a nice chunk of change. 

Kemp is the leader in that category as he is still owed $107 million over the next five seasons, and considering the trade markets for Crawford and Ethier are virtually nonexistent, this front office will have to get creative. Trading Kemp is the most likely scenario since he is their most attractive piece during a time when offense is a more coveted commodity than at any time in the last two decades.

Mark J. Terrill/Associated Press

Teams exploring a Kemp deal—the Seattle Mariners, San Diego Padres and Baltimore Orioles among them—might be rooting for Lester to land in Los Angeles. That could mean the Dodgers would want to trim Kemp’s salary and would be more willing to trade him for a lesser package, although that might just be wishful thinking by other teams looking for an MVP-caliber bat (when healthy) or those just not wanting L.A. to have so many impact stars.

Of course, Lester can’t solve all of the Dodgers' problems, but dropping him near the front of that rotation would certainly make the boys in blue downright scary to face at any point during the season, and even more so come next October.

If Lester sticks to his plan to make a decision before the winter meetings, we will know the outcome of Los Angeles’ aggressive last-minute push in the next few days.

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.