Evidence strongly supports that this prediction came true.

• On December 14–17, 2021, just as in the podcast timeframe, Mayor London Breed announced and then formalized a Tenderloin crime and drug crackdown, including flooding the neighborhood with more police, seeking more police funding, and declaring a state of emergency—explicitly framed as getting more “aggressive with law enforcement” and cracking down on open-air drug dealing and associated crime. (californiaglobe.com)
• On December 20, 2021, District Attorney Chesa Boudin publicly opposed Breed’s crackdown. In a San Francisco Chronicle report, Boudin joined other officials and activists “to criticize Mayor London Breed’s plan to flood San Francisco’s Tenderloin neighborhood with police and crack down on drug dealers as well as people who use drugs in the open,” arguing the plan relied on failed, punitive policies and calling instead for treatment and housing. (sfchronicle.com) This is direct, public disagreement with her policing/crime agenda.
• Coverage of the period describes an increasingly fraught relationship between Breed and Boudin as crime and disorder became central political issues; Breed moved toward a more law‑and‑order posture, while Boudin championed reform and resisted punitive crackdowns. (sfchronicle.com) That tension culminated in Boudin’s June 7, 2022 recall, after which Breed appointed a tougher‑on‑crime DA, Brooke Jenkins, to replace him. (en.wikipedia.org)

The prediction stated that within the next political cycle after December 2021, Breed would “butt heads” with Boudin because he would not support her tougher policing/crime‑control agenda. The documented events show exactly that: Breed advanced a policing‑heavy crackdown plan; Boudin refused to support it and publicly criticized it, leading to an open policy clash that extended into 2022. Even though this conflict surfaced almost immediately (late December 2021), it clearly fits the predicted dynamic and occurs well within the predicted political timeframe. Therefore, the prediction is best judged as right.