What are the benefits to signing a player during their first year of Arb to a long term deal. I had mistakenly thought that by doing so, it would make them more likely to re-sign after their first long term deal had completed, but this has not been the case from a small sample set that I have seen. If the goal is to hold onto a great player for as many ML seasons as possible, is it better to go to two years of Arbitration and then sign a 5 year deal?

It's cheaper.

His long-term demands are generally cheaper in his first arb season than they will be in his second arb season. So the upside is that you can lock him up for cheaper for future seasons while most likely paying more in the current season.

Downside is that he reaches the end of his first long-term deal a season sooner.

IMO, the only situation where it makes sense is if

1) the guy has a high patience rating and can be re-signed when his first LT deal is up.
2) you have extra cap space in the current season.

i always wait until arb2 or arb3, personally.

tec's wife must not let him talk at home.

No. I rarely can get a word in. I've given up trying.

Quote: Originally Posted By MikeT23 on 1/30/2010tec's wife must not let him talk at home

It's the secret to a long and happy marriage. KEEP YOUR MOUTH SHUT!

Coming up on my 35th anniversary. It's worked well for me.

In the end a LT deal is not cheaper for many cases. Lets say you go arb. 1.9m then 6.2 x 5. Other scenario is to go 5.8mx5 right away.

You might save 400k per year (going LT early) but that first year you save almost 4m (going Arb. the first year).

And you always guarantee 6 years instead of only 5 with the player (in case he leaves after the 1st LT).

Now granted sometimes going LT 1st or 2nd year is wider than 400k which is why I said at times it can be cheaper. C and 1B can be good example here because they don't usually ask for a ton.

Or you can give the player what he asks for in the first 2 arbs, then sign him to a 5 year deal, and in my experience they've always been willing to resign again since you never beat them in arb. Just make sure to resign them during their final season of the 5 year contract, not after rollover.