Actually, if your probe starts off retrograde, you can get an even bigger slingshot.
We start off with Voyager and Jupiter far away from each other. At this point, we can consider them to be in independent orbits around the sun. Jupiter is in an approximately spherical orbit, and the probe is probably in an eliptical orbit, tangent to both the Earth’s orbit (because that’s where it was launched from) and to Jupiter’s. The probe’s launch was timed such that it’ll reach the apihelion of its orbit (far point from the Sun) just as Jupiter is reaching that same point. When the probe reaches the collision point, it’ll be going slower than Jupiter.
In the usual case, the probe will be orbiting the Sun in the same direction as both Jupiter and the Earth, so Jupiter is catching up to the probe. The probe has speed V[sub]p[/sub], and Jupiter has speed V[sub]J[/sub]. That means that the relative speed of the probe and Jupiter is V[sub]J[/sub] - V[sub]p[/sub] .
Now, Jupiter and the probe get really close together. Now, Jupiter has much more gravitational influence on the probe than the Sun does, so let’s switch to Jupiter’s frame of reference. In Jupiter’s frame of reference, Jupiter is at rest, and the probe comes in at speed V[sub]J[/sub] - V[sub]p[/sub] . It swings around the planet on a very tight orbit, and comes back out in almost opposite the direction that it came in. In other words, after the encounter, the probe has a speed relative to the Sun of 2*V[sub]J[/sub] - V[sub]p[/sub] , which is a good bit greater than the original speed.
OK, that’s the standard case. Now let’s look at the retrograde case your friend is talking about. In this case, instead of Jupiter catching up to the probe, we’ve got a head-on collision. The objects approach each other at a speed of V[sub]J[/sub] + V[sub]p[/sub], so after the interaction, they’ll be receding from each other at that same speed, and the final speed of the probe will be 2*V[sub]J[/sub] + V[sub]p[/sub], which is actually faster than if they’re going the same direction.
So, to sum up: The direction of the orbits does matter, but not in the way that your friend claims. A retrograde slingshot gives you more than a prograde slingshot, not less.