When wind speeds are 2–10 m s
−1
, reflective contrasts in the ocean surface make oil slicks visible to synthetic aperture radar (SAR) under all sky conditions. Neural network analysis of satellite SAR images quantified the magnitude and distribution of surface oil in the Gulf of Mexico from persistent, natural seeps and from the Deepwater Horizon (DWH) discharge. This analysis identified 914 natural oil seep zones across the entire Gulf of Mexico in pre‐2010 data. Their ∼0.1 µm slicks covered an aggregated average of 775 km
2
. Assuming an average volume of 77.5 m
3
over an 8–24 h lifespan per oil slick, the floating oil indicates a surface flux of 2.5–9.4 × 10
4
m
3
yr
−1
. Oil from natural slicks was regionally concentrated: 68%, 25%, 7%, and <1% of the total was observed in the NW, SW, NE, and SE Gulf, respectively. This reflects differences in basin history and hydrocarbon generation. SAR images from 2010 showed that the 87 day DWH discharge produced a surface‐oil footprint fundamentally different from background seepage, with an average ocean area of 11,200 km
2
(SD 5028) and a volume of 22,600 m
3
(SD 5411). Peak magnitudes of oil were detected during equivalent, ∼14 day intervals around 23 May and 18 June, when wind speeds remained <5 m s
−1
. Over this interval, aggregated volume of floating oil decreased by 21%; area covered increased by 49% (
p
< 0.1), potentially altering its ecological impact. The most likely causes were increased applications of dispersant and surface burning operations.
The Taylor Energy Site is located in the vicinity of the Mississippi Delta region over the Northern Gulf of Mexico (NGoM). Surface oil patches have been persistently observed within this site since 2004, when an oil rig was destroyed by Hurricane Ivan. A multiplatform observational experiment was conducted in April 2017 to investigate, for the first time, the main hydrocarbon pathways from the Taylor Energy Site toward the NGoM continental shelves, and the Gulf interior, under the influence of local and regional physical processes. Results indicate that the Mississippi River (MR)‐induced fronts over the Taylor Energy Site, in combination with local circulation, prevailing winds and broader regional dynamics determine the hydrocarbon transport. The drifters deployed during the field experiment, in tandem with satellite data, drone imagery, wind measurements, and radar‐derived data, efficiently described three major hydrocarbon pathways, associated with MR plume dynamics (downstream/upstream coastal currents) and basin‐wide circulation (offshore pathway). Two different types of drifters, drogued and undrogued, showed clearly different pathways, which suggest potential differences in the expected advection of oil, depending on whether it forms a surface slick or whether it is partially mixed below the surface. The existence of multiple river fronts influenced the fate of oiled waters, preventing the hydrocarbons from reaching the Delta, like a natural boom barrier, trapping and directing the oil either westward or eastward. Thermohaline measurements showed that the MR plume near Taylor was 5–10 m deep, while the clearer ocean was characterized by a 40 m upper ocean homogenous layer.
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