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Simple Summary: Despite advances in surgical techniques and systemic therapy, some patients with multifocal, bilobar colorectal liver metastases remain unresectable. The surgical debulking of liver tumor burden may increase median survival in combination with chemotherapy compared to chemotherapy alone. This study retrospectively evaluated the efficacy of surgical debulking alongside chemotherapy versus chemotherapy alone and found those who underwent debulking surgery showed improved survival compared to those who did not. These findings advocate for further investigation through a randomized trial to evaluate intentional debulking as a potential treatment strategy for unresectable colorectal cancer liver metastases. (1) Background: Despite advances in surgical technique and systemic chemotherapy, some patients with multifocal, bilobar colorectal liver metastases (CRLM) remain unresectable. These patients may benefit from surgical debulking of liver tumors in combination with chemotherapy compared to chemotherapy alone. (2) Methods: A retrospective study including patients evaluated for curative intent resection of CRLM was performed. Patients were divided into three groups: those who underwent liver resection with recurrence within 6 months (subtotal debulked, SD), those who had the first stage only of a two-stage hepatectomy (partially debulked, PD), and those never debulked (ND). Kaplan–Meier survival curves and log-rank test were performed to assess the median survival of each group. (3) Results: 174 patients underwent liver resection, and 34 patients recurred within 6 months. Of the patients planned for two-stage hepatectomy, 35 underwent the first stage only. Thirty-two patients were never resected. Median survival of the SD, PD, and ND groups was 31 months, 31 months, and 19.5 months, respectively (p = 0.012); (4) Conclusions: Patients who underwent a debulking of CRLM demonstrated a survival benefit compared to patients who did not undergo any surgical resection. This study provides support for the evaluation of intentional debulking versus palliative chemotherapy alone in a randomized trial. [ABSTRACT FROM AUTHOR]