Background: The surgeon’s intraoperative assessment of the curative potential of tumor resection following gastrectomy adds new information that could help clinicians and patients by predicting survival. Methods: All patients in Sweden undergoing gastric cancer resection between 2006 and 2018 were grouped according to a prospectively registered variable; the surgeon’s intraoperative assessment of the curative potential of surgery: curative, borderline curative, or palliative. Factors affecting group allocation were analyzed with multivariable logistic regression, while survival was analyzed using multivariable Cox regression and the Kaplan–Meier method. Positive predictive value (PPV) and negative predictive value (NPV) were calculated. Results: Of 2341 patients undergoing gastric cancer resection, 1547 (71%) were deemed curative, 340 (15%) borderline curative, and 314 (14%) palliative (140 missing assessments). Advanced stage increased the risk of borderline curative resection (Stage III, odds ratio (OR) = 6.04, 95% confidence interval (CI) = 3.92–9.31), as did emergency surgery OR = 3.31 (1.74–6.31) and blood loss >500 mL; OR = 1.63 (1.06–2.49). Neoadjuvant chemotherapy and multidisciplinary team (MDT) discussion both decreased the risk of borderline curative resection, OR = 0.58 (0.39–0.87) and 0.57 (0.40–0.80), respectively. In multivariable Cox regression, the surgeon’s assessment independently predicted worse survival for borderline curative (hazard ratio (HR) = 1.54, 95% CI = 1.29–1.83) and palliative resections (HR = 1.76, 95% CI = 1.45–2.19), compared to curative resections. The sensitivity of the surgeon’s assessment of long-term survival was 96.7%. The PPV was 50.7% and the NPV was 92.1%. Conclusion: The surgeon’s intraoperative assessment of the curative potential of gastric cancer surgery may independently aid survival prediction and is analogous to prognostication by pathologic Staging. Advanced disease, emergency surgery, and a high intraoperative blood loss, increases the risk of a borderline curative or palliative resection. Conversely, neoadjuvant treatment and MDT discussion reduce the risk of borderline curative or palliative resection.