The declining phases of solar cycles are known for their high speed solar wind streams that dominate the geomagnetic responses during this period. Outstanding questions about these streams, which can provide the fastest winds of the solar cycle, concern their solar origins, persistence, and predictability. The declining phase of cycle 23 has lasted significantly longer than the corresponding phases of the previous two cycles. Solar magnetograph observations suggest that the solar polar magnetic field is also ∼ 2 – 3 times weaker. The launch of STEREO in late 2006 provided additional incentive to examine the origins of what is observed at 1 AU in the recent cycle, with the OMNI data base at the NSSDC available as an Earth/L1 baseline for comparisons. Here we focus on the year 2007 when the solar corona exhibited large, long-lived mid-to-low latitude coronal holes and polar hole extensions observed by both SOHO and STEREO imagers. STEREO provides in situ measurements consistent with rigidly corotating solar wind stream structure at up to ∼ 45° heliolongitude separation by late 2007. This stability justifies the use of magnetogram-based steady 3D solar wind models to map the observed high speed winds back to their coronal sources. We apply the WSA solar wind model currently running at the NOAA Space Weather Prediction Center with the expectation that it should perform its best at this quiet time. The model comparisons confirm the origins of the observed high speed streams expected from the solar images, but also reveal uncertainties in the solar wind source mapping associated with this cycle’s weaker solar polar fields. Overall, the results illustrate the importance of having accurate polar fields in synoptic maps used in solar wind forecast models. At the most fundamental level, they demonstrate the control of the solar polar fields over the high speed wind sources, and thus one specific connection between the solar dynamo and the solar wind character.