A.J. Preller capped a radical offseason overhaul Sunday night by agreeing to a four-year deal with right-hander James Shields, who's poised to sign the biggest contract in San Diego Padres history.
Though Shields will reportedly earn $75 million over the next four years, his new contract doesn't approximate the nine-figure deal he was thought to be seeking when the offseason began. Preller took advantage of the tepid market for Shields's services, finalizing a deal with an average annual salary of $18.75 million - a figure that, while substantial, doesn't inspire awe in baseball's current economic landscape.
As such, it's hard to believe that other teams with dubious starting pitching - especially those with deep pockets - weren't more aggressive in trying to acquire Shields.
Here are three teams that will likely regret not signing the former All-Star.
Boston Red Sox
Resolved to return to the top of an increasingly murky division, Red Sox general manager Ben Cherington labored this winter after watching his club stumble to a 71-91 record one season after hoisting the Commissioner's Trophy.
A pair of trades added left-hander Wade Miley and right-hander Rick Porcello to Boston's rotation before Cherington brought Justin Masterson back to the organization that drafted him on a one-year deal.
Following the departure of Jon Lester, however, and last season's trade with the Cardinals that sent John Lackey to St. Louis, the Red Sox have no starters that truly make opposing hitters uncomfortable. Though the club boasts considerable depth - its stable of arms augmented by prospects Henry Owens and Eduardo Rodriguez - the lack of premium talent in its rotation puts further pressure on its revamped lineup to score runs (Boston scored fewer runs per game than all but two AL teams in 2014, though the additions of Hanley Ramirez and Pablo Sandoval should rectify that).
The addition of Shields could have provided the Red Sox with an extra 3-4 wins - a bump that could be the difference in crowning a division champion - while also enabling the club to move Joe Kelly (and his platoon splits) to the bullpen.
Miami Marlins
Shortly after finalizing a 13-year extension with Giancarlo Stanton, the Marlins brokered a series of moves designed to surround the 25-year-old with a team capable of reaching the postseason.
Most of the additions, however, were made to improve the club's lineup rather than its lackluster rotation - which will be without Jose Fernandez until at least June. Mat Latos, who regressed in 2014, is primed to lead a rotation featuring Jarred Cosart, Henderson Alvarez and Dan Haren - none of whom boast considerable upside.
After unloading a slew of veterans prior to the 2013 season, the Marlins remain overwhelmingly free of cumbersome financial obligations and have committed only about $59 million toward their 2015 payroll before arbitration figures. Armed with considerable financial flexibility, they erred in failing to land Shields, whose presence could have helped Miami fend for a wild-card berth this year.
San Francisco Giants
Giants general manager Brian Sabean proved himself an unfailingly loyal executive this offseason, re-signing both Jake Peavy and Ryan Vogelsong - two seasoned starters who helped San Francisco to a World Series championship four months ago - despite the likelihood of diminishing returns from both.
Sabean's decision to re-invest in the staff that led the Giants to glory came shortly after the club failed to land Lester, the highly-coveted free agent who was linked to San Francisco early in the offseason. Though Shields would have afforded the Giants a nice consolation prize, the club was reportedly "out" on the 33-year-old by early January.
Shields, though, seemed like a perfect fit for the Giants, who are ostensibly built to contend but received less value from their starters in 2014 than all but two teams. Beyond Madison Bumgarner, the Giants' rotation is littered with aging veterans who have struggled lately either with effectiveness or health problems.
A deal with the Giants would have also fulfilled Shields's desire to pitch on the West Coast, while helping San Francisco recoup value lost in the Sandoval trade.
