Baseball's front-office execs with the most to prove this winter

Is Phillies GM Matt Klentak ready to deliver on expectations of contention? Eric Hartline/USA Today Sports

As the director of baseball operations and assistant general manager for the Oakland Athletics and then as the general manager for the Los Angeles Dodgers, Farhan Zaidi has been a major figure in assembling the rosters of postseason-bound teams for seven straight seasons. The 42-year-old executive will be hard-pressed to keep that streak alive, however, because earlier this month, he accepted an offer to become the president of baseball operations for the Giants, losers of 187 games the past two seasons, including 89 in 2018.

Zaidi inherits a number of challenges, but he's hardly the only executive who will be under the microscope this winter while refashioning his team for 2019 and beyond. What follows is a look at five executives who have their work cut out for them this winter, particularly as their teams missed the playoffs in 2018. Note that some of these execs are billed as general managers and others as presidents of baseball operations. By either title, they're generally understood to be the faces of their respective front offices when it comes to the big baseball decisions.

The executives are listed based on the 2018 records of their teams, with the worst first.

Farhan Zaidi, San Francisco Giants (73-89, fourth in NL West)

Zaidi inherits a team that had the National League's highest Opening Day payroll ($200.5 million, according to Cot's Contracts), its oldest lineup (weighted age of 29.8 years, according to Baseball-Reference) and its worst park-adjusted offense (82 wRC+, according to FanGraphs), not to mention a bottom-four rotation in terms of park-adjustments (104 ERA-minus, 110 FIP-minus) and a farm system that Baseball America ranked as the majors' eighth-worst in August and that FanGraphs ranked as the seventh-worst earlier this month. The franchise's twin pillars, Buster Posey and Madison Bumgarner, are coming off injury-shortened seasons, as are three of the other six players making at least $12 million in 2019 (Brandon Belt, Mark Melancon and Jeff Samardzija). Another, Johnny Cueto, had Tommy John surgery in August.

Given that mess, the burning question is