Cubs Draft Pick Retires After Six Years Without Reaching the Majors

A former high draft pick steps away from baseball after years of perseverance in the minors, signaling both an end and a reminder of the Cubs evolving farm system.

Chase Strumpf Retires: Former Cubs Second-Round Pick Steps Away from Baseball

Six years after being selected 64th overall in the 2019 MLB Draft, Chase Strumpf is stepping away from professional baseball. The 27-year-old infielder, who spent the last few seasons with Triple-A Iowa, has officially retired, closing the book on a career that showed flashes of promise but ultimately never broke through to the Major League level.

Strumpf came out of UCLA with a reputation as a polished college bat. The Cubs saw enough in his offensive profile to make him a second-round pick, betting on his on-base skills and positional versatility.

And for a while, it looked like that bet might pay off. While his career batting average in the minors sat at .231, the more telling number was his .364 on-base percentage-a sign that Strumpf understood the strike zone and could work a count, even if the hits didn’t always fall.

Defensively, he proved to be a valuable piece for Iowa, logging innings at first, second, and third base. That kind of flexibility kept him in the lineup and gave the Cubs options as they evaluated their infield depth. But the bat never quite clicked at the level needed to earn a call-up, especially in a system that’s been quietly reloading with younger, higher-ceiling talent.

Strumpf never cracked a top-100 prospect list and last appeared in the Cubs' organizational top-30 in 2023, landing at No. 25.

Still, he had a stretch last season where things started to click, showing the kind of offensive production that once made him a Day 1 draft pick. It just wasn’t enough to force the Cubs’ hand, especially during a year when their bench saw plenty of turnover.

As Strumpf moves on to the next chapter, he leaves behind a solid minor league career and a reputation as a reliable clubhouse presence-something that doesn't always show up in stat lines but matters in the grind of a 140-game season.

Cubs' Infield Pipeline Still Stocked

With Strumpf retiring, the Cubs lose a seasoned minor league infielder, but the organizational depth chart remains strong. Jefferson Rojas is currently the top-ranked infield prospect in the system, sitting at No. 4 overall. Rojas, still a couple of years away from Wrigley, brings a high-upside profile and has steadily climbed the ranks.

Another name to watch is Jonathon Long, though his path just got a little more complicated. The Cubs recently added former Yankees prospect Tyler Austin on a one-year deal, which could push Long further down the pecking order, at least in the short term.

Then there’s Matt Shaw, a former first-round pick who’s likely to be in the mix for a big-league role in 2026-assuming he’s not moved in a trade. Shaw has the kind of offensive upside that could fast-track him to the Majors, and his development will be something to watch closely this coming season.

While the infield is in decent shape, the Cubs’ real strength lies in the outfield. With the big-league trio already in place, prospects like Owen Caissie and Ethan Conrad are waiting in the wings. Caissie is knocking on the door, and Conrad isn’t far behind, giving the Cubs a chance to either promote from within or leverage that depth in trade talks.

Pitching Still the Missing Piece

The biggest challenge for the Cubs remains the same: developing homegrown pitching. Cade Horton stands out as a recent success story, but he’s more of an outlier than a trend-setter. For Chicago to build a sustainable, cost-controlled contender, they’ll need more Hortons-arms that can rise through the system and contribute meaningfully at the big-league level.

Until then, the Cubs will continue to rely on positional depth and smart roster construction. Strumpf may not have made it to the Majors, but his journey is a reminder of how tough that final leap can be-even for talented, high-drafted players.