OAKLAND — Gather ‘round!
Skip had a message he wanted to relay to us, his ragtag bunch of wannabe ballplayers. We hustled in front of the third-base dugout and listened up.
“Five words,” Aaron Miles, second-year manager of the Pioneer League Oakland Ballers, told us. “Don’t quit your day jobs.”
It stood in contrast to the words of encouragement he shared from the same spot a few hours earlier to the 50 actual ballplayers who paid to be there. But the bottom line wasn’t so different.
Oakland City Councilmember Ken Houston, left, and Oakland Interim Mayor Kevin Jenkins high-five one another as Oakland Ballers manager Aaron Miles, right, looks on after participating during the Oakland Ballers open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
Whether it was us, the 10 media members, social media influencers and local politicians invited to take part in the independent team’s second annual open tryout over the weekend at Raimondi Park, or the guys with metal spikes and baseball pants, we were all varying degrees of long shots for a roster much closer to full form that it was a year ago.
Two months out from the start of their second season, the Ballers are on their most stable footing yet, co-founder Paul Freedman tells me behind the batting cage.
Freedman left his job running an education startup to follow his passion as an Oakland baseball fan for days like today. Donning a Ballers cap and a No. 81 tryout jersey on a picture-perfect morning with the pitching machine whirring in the background, Freedman says, “This has been the most difficult business I’ve ever done but easily the most rewarding.”
The A’s fanbase gave Freedman a sense of community, and when that was taken away from them, he wanted to provide something in return. They came out in droves — 100,000 fans over 50 home dates in their inaugural season at their renovated West Oakland digs — and now, in year two, the B’s will be the only game in town.
It cost $140 for a shot to be more than just a fan, and players of all stripes took up the opportunity. Young and old. Gray beards, beer bellies, six-packs and superhero-like statures. But they weren’t the only ones who wanted a slice.
The Ballers will return about half the roster that made a second-half playoff push last season, and they’ve announced eight free-agent signings since the end of January. They added two more via trade and another through the draft.
Three attendees last year made the cut to go to spring training. One, Kelsie Whitmore, made the team as the Pioneer League’s first female player. Another, San Francisco native Andrew Martinez, would join the roster later. And the third, Vacaville pitcher Connor Caporale, was eventually cut but signed elsewhere.
The opportunities may be even fewer and farther between for this year’s group.
At least for now, assistant general manager Tyler Petersen tells me from the right field grass. After running the 60-yard dash, the players are going through their second drill of the day — throws to third base and home plate to show off their arm strength and accuracy — and Petersen is booming out each name and number for the coaches on the infield.
The typical Pioneer League team may have one player snatched up by a major-league organization per season, Petersen explains. In their first year, the Ballers had four.
When the call comes, like it did for Tyler Davis last May, it often happens fast. One morning, Petersen was fielding a call from a White Sox official inquiring about a pitcher, and that afternoon, the Ballers announced the signing in front of their home fans.
“That is probably the one I’m most proud of,” Petersen says, “because he was mine.”
Petersen, a broadcaster by trade, rose through the independent league ranks by chance and when his hometown Ballers came calling in October 2023, became Freedman’s first employee.
Davis, a shortstop from Sam Houston State, was one of the first names Petersen brought to Don Wakamatsu, the vice president of baseball operations, that November. It took until May to finalize the signing. Davis touched 98 mph on the mound, and within a month, he was gone.
That is the ideal outcome for any Pioneer League player, and the Ballers are attempting to make the case that they offer a better chance at it than the league’s other 11 teams.
Petersen uses his video production background and data from the Trackman cameras the team had installed at Raimondi Park to create unique ways to showcase the B’s players to affiliated clubs, and the crowds at Raimondi have already made it an attractive destination for players.
Prospect player Kevin Gameros participates during the open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
While the club boasts a potential fanbase of 7.8 million-plus in its presentation to potential investors, the Bay Area market presents its challenges, too.
Back for his second season with the club, pitching coach Jim Dedrick needled Petersen on the infield as players stretched. His car window was smashed three times last season and his upstairs neighbor stomped around like he was 400 pounds.
Dedrick, like most of the Ballers’ roster, comes from out of town. The rest of the league exists in small markets such as Idaho Falls, Idaho; Billings, Montana; and Ogden, Utah, where real estate is more affordable and players are often housed with host families.
That’s not an option for the Ballers, who don’t want their players spread out in far-flung corners of the Bay Area. In fact, Petersen says, the team is looking into acquiring its own apartments in nearby Emeryville.
But when the day during the season comes when Petersen needs someone — fast — that’s when he begins going through the list of local standouts from the open tryout.
There are 26 roster spots, Miles tells the attendees in his opening remarks, but the Ballers used 40 players last year. “We’re not gonna sign seven guys today,” he says. “But some of you, we’ll remember.”
Oakland Ballers manager Aaron Miles announces the selected players after participating in the open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
Miles offers some advice to the hopefuls, and my ears perk up from the back of the group. After the 60-yard dash, fielding ground balls and making throws, the players will split off into six groups for batting practice, but the whole day is leading up to the afternoon’s live scrimmage.
During their lunch break is our time to shine.
Miles tells the players: Show off your arm, show off your speed and, he emphasizes, do not bunt. “I’m not gonna remember a bunt,” he says. I take it to heart.
Last year, the media tried out alongside the players. In their second go-around, apparently having learned better, the Ballers opted to split us off into an abbreviated portion.
The mere invitation raises questions that don’t often come to the forefront for someone who hasn’t played baseball competitively since high school. How do I re-lace a glove? Can I expense a cup? Do I need to bring my Green Day CDs??? (Billie Joe Armstrong, the Ballers’ newest investor with Too $hort, was on tour on a separate continent, to my disappointment.)
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It’s me, a couple of Oakland city council members, the rapper JWalt and a group of influencers who I’m sure have large followings but have never appeared in my algorithm.
Trainers from the Ballers’ partner gym were there to warm up all the players, and they put us through the same stretching routine — guess who needed it more.
We headed next to the outfield, where we got three chances to show off (or permanently damage) our arms — for those of us who could first successfully field the ball (two out of three!).
Then to the infield, where we were warned about the choppy dirt and my concerns about expensing protective equipment turned into thoughts about hospital bills and misery.
I survived. My reward? Ten cuts in the batting cage. And you’d better believe I didn’t bunt. Journalistic integrity implores me to tell the truth, so let it be documented in newsprint that I laced a standup double on my last swing. (History can omit that it was with a metal bat.)
So maybe I won’t quit my day job.
But I might just try out for real next year.
Bay Area News Group reporter Evan Webeck hits a double during the Oakland Ballers open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
Oakland Ballers manager Aaron Miles, middle, is ready to make the cuts after prospect players participated in the open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
Bay Area News Group reporter Evan Webeck participates during the Oakland Ballers open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
Oakland Ballers manager Aaron Miles, left, and pitching coach Jim Dedrick look on during the open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
Oakland City Councilmember Ken Houston, left, and Bay Area News Group reporter Evan Webeck participate during the Oakland Ballers open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
Prospect players participate in the Oakland Ballers open tryouts at Raimondi Park in Oakland, Calif., on Saturday, March 8, 2025. (Ray Chavez/Bay Area News Group)
