Pretty much every online league I'm in I've been able to do that, which is why I put rules in place to prevent it from happening. Works best pre-arb. I'm no longer in this league, for example, but
Player Report for #4 Tristan Metten is a good example (Signed a 9-year contract extension worth a total of $11,160,000 with the Philadelphia Phillies organization.).
Player Report for #13 Max Sapp is another example in a league I'm currently in, Signed a 8-year contract extension worth a total of $9,600,000 with the Oklahoma City RedHawks organization. So not 10 years, in this case, but in this league service time leads to FA a year earlier, so the 8/9 year deals cover the same amount of FA years.
I try not to do these deals because I feel bad exploiting what is a very poor contract system, but it's easy enough to do when you know when to do it. It's not about waiting for a poor year either.
I find arb values to be way too low. For elite players if I get an arb value of less than 10M (and it happens far too often) then it's really not being done properly. Like I said before a guy coming off back to back second place Cy Young finishes should not be sitting @ 5M, it should be way higher.