In high school there were certainly some schools that field small track teams where I sometimes would run a random event just to collect the points (we were also a small team) and won with some bad times. I liked to think of myself as the Jose Oquendo of high school track; during my sophomore year I competed in all 16 events over the course of the season. Probably the one that stands out is getting asked to run the IM hurdles with about 2 minutes notice by my coach as the other team only had two runners and I ended up finishing first but it was definitely not a great time and I ended up getting yelled at by the coach b/c I waved to my teammates down the stretch when it was clear I was going to win. I personally found that to be the worst race in terms of how I felt afterwards so I stuck with the mile and 4x400 as my primary events.
Today I run a lot of 5K and 10Ks and sometimes if the weather is crappy or the field is small I have finished first with fairly so-so times, I think it's a factor of the field size and weather. For example I did a Turkey trot once that offered a 5K and 10K on a loop course where the first loop was 5K and the 10K was supposed to do a 2nd loop. It was 24 degrees and snowing and so that winnowed the field to about 200 from the usual 400 or 500 and although their were some strong runners (one person in the field who finished first the prior year in just under 31 minutes decided to bail after 5K (along with most of the field) so I was able to beat out about a couple of dozen hearty runners with a time that wasn't that far under 40 minutes. Think about the Boston marathon in 2018, both the male and female winners weren't favorites and ran pretty slow times vs. a typical year but that's b/c the conditions were so horrendous and a lot of the favorites dropped out before the finish.
Another race I didn't win but was with the lead pack of a trail race that was misdirected by an official on the course and we all ended up running an extra 500 or 600 meters with some serious elevation gain allowing a slower runner who stayed on course to win.
I don't think most recreational runners are doing small races or Turkey Trots for bragging rights but rather b/c it's fun and they enjoy the comradery. That said some of the best prizes I've gotten have been for winning small local races vs. some of the larger events I've run. I find that unless you are in a truly elite race like the Peachtree or Falmouth, etc. the prizes leave much to be desired but sometimes the local rotary club might get some some pretty good prize packages from local businesses like spa and restaurant gift certificates, beer, wine, etc.