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Evaluating what the future holds for the Oakland A’s after key trade deadline

MLB trade deadline: Oakland Athletics acquired four prospects including left-handed starter Ken Waldichuk in a deal that sent Frankie Montas to the Yankees

OAKLAND, CA – JUNE 8: Oakland Athletics Executive Vice President of Baseball Operations Billy Beane walks off the field before the start of a MLB game against the Arizona Diamondbacks at the Coliseum in Oakland, Calif., on Tuesday, June 8, 2021. (Ray Chavez/Bay Area News Group)
OAKLAND, CA – JUNE 8: Oakland Athletics Executive Vice President of Baseball Operations Billy Beane walks off the field before the start of a MLB game against the Arizona Diamondbacks at the Coliseum in Oakland, Calif., on Tuesday, June 8, 2021. (Ray Chavez/Bay Area News Group)
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The next time the Oakland A’s are competing for a playoff berth, left-handed pitcher Ken Waldichuk could be the ace leading the postseason push.

Waldichuk, who pitched in college at Saint Mary’s in Moraga, was the headliner of the prospect package the A’s received in return for sending starter Frankie Montas and reliever Lou Trivino to the Yankees Monday.

After dealing two veteran pitchers Monday, Tuesday was quiet for an A’s team that now has a big hole to fill in its rotation the rest of the way. It’s possible two of the prospects acquired Monday –Waldichuk and fellow lefty JP Sears– could provide help sooner rather than later.

Since being selected in the fifth round of the 2019 MLB amateur draft by the Yankees, Waldichuk’s stock has risen dramatically thanks to eye-popping strikeout totals and a three-pitch mix (fastball, curveball, changeup) that has neutralized minor league foes.

Ranked as the No. 5 prospect in the Yankees’ farm system, Waldichuk was one of three pitching prospects Oakland added in a deal that also brought  Sears, right-hander Luis Medina and infielder Cooper Bowman to an A’s farm system that has been replenished in a significant way over the last six months.

With 116 strikeouts over 76 1/3 innings across two minor league levels this season, Waldichuk has demonstrated frontline starter potential and could make his major league debut later this month. For now, Waldichuk is expected to begin his A’s tenure at Triple-A Las Vegas, where he’ll join Sears, a 26-year-old southpaw who made his debut earlier this season with the Yankees.

Together, the lefties could find themselves in the middle of a 2023 A’s rotation that may still be waiting on reinforcements from trades executives Billy Beane and David Forst made during spring training. In deals that sent Matt Chapman, Matt Olson, Sean Manaea and Chris Bassitt elsewhere, Oakland loaded up on starting pitching prospects, acquiring former first-round draft picks Gunnar Hoglund, JT Ginn and Ryan Cusick, who all need more minor league seasoning before they’ll receive a chance to help form the A’s next homegrown core.

With Waldichuk and Sears on the verge of receiving consistent opportunities in Oakland, the other prospects the A’s acquired Monday are farther away from helping the major league club. Medina might have the highest ceiling of any of the players added thanks to a fastball that has reportedly touched 103 miles per hour on the radar gun, but he’s walked 40 batters in 72 innings this year and will likely need to develop better control before jumping from Double-A to Triple-A.

As for Bowman, he’s the least exciting prospect the A’s acquired in the deal with New York in part because he has hit just .217 with a .698 OPS at High-A this season. The Louisville product has stolen 35 bases this season, but has also struck out in nearly one-third of his at-bats this year.

If the A’s set out at the beginning of their latest rebuilding process to develop a homegrown starting rotation, they’ve added an impressive mix of pitchers who should give Oakland the chance to have a solid group of young arms by 2024 at the latest. What the A’s front office has not done, however, is find the type of high-upside position players who could have seemingly been available in trades for controllable talent such as Chapman, Olson and Montas.

In the Montas deal, the A’s were unable to pry either of the Yankees’ top shortstop prospects, Anthony Volpe or Oswald Peraza, who would have instantly become the best position players in Oakland’s farm system. That might not be a major issue if 2021 first-round draft choice Max Muncy develops into a star, but Muncy has struggled at the plate in each of his first two minor league seasons.

Even with the trade deadline in the rearview mirror, the process of restocking the farm system will likely continue into the offseason. Oakland didn’t trade catcher Sean Murphy or outfielder Ramón Laureano on Tuesday, but both players (especially Murphy) could be coveted by contenders in offseason trades that would enable the A’s to address more pressing areas of need around the diamond.

With catching prospect Shea Langeliers, who was acquired in the Olson deal with Atlanta, on the cusp of his big league debut and recent first-round draft picks Tyler Soderstrom (2020) and Daniel Susac (2022) expected to follow within the next few years, trading a Gold Glove Award winner in Murphy for multiple players in return appears to be the next domino to fall if the A’s hope to have a chance of contending by 2024 or 2025.

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