That is an interesting paradox, but it is flat out wrong. If you take two remote control cars (one capable of 40 mph and one capable of 20 mph) and you have the 40 mph car take off, then half a minute later the 20 mph car and they are both going the same direction for 1 mile. Which one will get there first? Now do the same with a couple of jet airplanes both flying the same direction leaving 30 minutes apart with the first one flying at Mach 5 and the second at Mach 2.5. Again the faster one will get there first. Frame of reference aside this is true.
Now with that said if you took two space ships, one traveling at .5c and one traveling at .25c and had them leave a year apart (with the faster one first), both traveling in the same direction. It would appear to us (hear on Earth) through Visual Observations that the slower one gets to the destination at the same time (or close to it) as the faster one. That is an optical illusion caused by speed. However, they would not arrive at the same time or even any where close to the same time. They would arrive relative to the distance/speed they where traveling just like the remote control cars or the jet planes.
However, relative the person(s) onboard the space crafts the persons on the slower (.25c) craft would age at almost three times the speed of those on the .5c craft.