Every winter, Oakland A’s general manager Billy Beane has one hand perpetually tied behind his back, as he tries to rebuild his rosters for the following season. Frugal ownership, a decrepit stadium, and multiple run-ins with raw sewage make the A’s one of the least desirable Major League Baseball landing spots for top free agents. So, Beane, the man profiled in Michael Lewis’ bestseller Moneyball, does his best to cobble together lineups with bargain basement prospects and aging journeymen. And because he’s exceptionally good at his job—and a little lucky—he manages to field competitive teams year after year.

The city of San Jose faces similar obstacles to recruiting and retaining the best and brightest minds to run the day-to-day operations of America’s 10th largest metropolis. Protracted battles between labor and management, and polarization on the current City Council, have left a shroud of distrust hanging over 200 E. Santa Clara St. like a funeral pall. Employees are leaving in droves, taking decades of experience with them. And we don’t have a Billy Beane in our front office to work his magic.

Since 2010, San Jose has seen the exodus of no less than 13 department heads*. That number that will increase to 14 when Joe Horwedel steps down as planning director at the end of the year. All but two of these positions, fire and human resources, have been filled, but some sat vacant for months, even years, while the city looked for viable replacements. National searches have been abandoned. Chosen candidates have backed out at the last minute. And our city has been left with a gaping hole in its institutional knowledge while elected leaders grapple with the most daunting fiscal challenges in recent memory.

So perhaps it should come as no surprise that City Manager Debra Figone unceremoniously announced last week that her deputy Ed Shikada will take her position when she rides off into the sunset of her pre-Measure B retirement package. No national search. No extensive outreach for public input. Not even an ad in the Mercury News. Just a closed-session council meeting and a rubber stamp. And just like that, the city of San Jose has a new CEO.

Now, don’t get me wrong. I don’t know Mr. Shikada personally. (I’ve watched him extensively on Civic Center TV, but that’s not really the same, is it?) By all accounts, he’s a thoughtful and dedicated public servant who’s more than capable of excelling in the heady job he’s just been handed. And as fellow Willow Glen-ers, we have an instant affinity. So much so that I’ll forgive him his master’s degree from UCLA (Fight On!).

But wouldn’t it be better if we’d looked all across the country for our next city manager, turned over every stone, pored over lengthy resumes, studied best practices from similar cities and regions, only to find the best possible option right here in our own backyard?

It would make me feel better about San Jose’s pipeline of leadership—our “farm team,” so to speak. And it would certainly inspire more confidence in Mr. Shikada, who faces the prospect of proving himself worthy of an open-and-shut promotion while making difficult decisions about city services in the midst of an ongoing budget crisis. Not to mention that the upcoming mayor’s election will saddle him with a new boss within his first year on the job.

It’s an exceedingly tight rope, and I truly hope Mr. Shikada manages to walk it safely. I also hope that he will use this opportunity to promote a new vision for San Jose and a new attitude at City Hall. But the odds are stacked against him—much like they are against the A’s every winter.

Peter Allen is an arts commissioner, nonprofit director, small business owner, and a proud native of San José.

* Airport, Emergency Services, Environmental Services, Finance, Fire, Human Relations, Information Technology, Library, Parks, Recreation & Neighborhood Services (PRNS), Police, Public Works, Retirement, and Transportation.