Why did Yosef think the Sar HaMashkim could help?

Question

There is criticism of Yosef for asking the Sar Hamashkim to mention him to Paroh, instead of trusting in Hashem, but what was Yosef even expecting from the Sar Hamashkim?

The poor man was just granted pardon and given the chance to return to his old job, after "sinning" to his master. Can he really assume the role of Paroh's strategic advisor for prisoners, and suggest that the poor Ivri boy should be released because he is really innocent?!

It seems that everything worked out in Yosef's favor - the Sar may have forgotten about him, but on the other hand it was only realistic for Paroh to listen to him after his troubling dream! This doesn't seem like a punishment, but another part of the Hashgacha Pratit that Yosef merited.

Can anyone explain -

1. What Yosef really expected, how he thought the Sar would help him.

2. Why the two year gap is viewed as a punishment, and not as necessary for the proper circumstances to bring about his release.

Answer 1

An analogous situtation in Tana"ch would be that of Nechemiah

And I was the king's butler.

and

Now it came to pass in the month of Nissan, in the twentieth year of King Artaxerxes, [that they brought] wine before him, and I carried the wine and gave [it] to the king. And I had never been sad in his presence.

This was actually a major position in court and he was not just a server. As a result he would be able to speak to Par'o bring up the one who had been able to tell what had happened and had been able to understand the dreams.

The dream itself could have come at any time. The description of the two years delay shows that it was significant, which is why the chazal connect it to the extravagant nature of the request and the two languages of "forgetting". Had he asked "once" instead of twice, Hashem could have had the dream come at once, when the butler was still riding high from having been declared innocent.

The translation of

Miketz 41:1

It came to pass at the end of two full years,

that the two full years are emphasized as a significant matter. Once the importance of the dream was understood, the butler (who was the chief food taster, and master of the household as well as a trusted advisor) was able to immediately speak up. Indeed he recognized that he had been at fault.

Miketz 41:9

Now the chief cupbearer spoke with Pharaoh, saying, "I call to mind my faults today.

Yet even here he denigrates Yosef. As Rav Hirsch points out, it was Yosef's character that led to the final result.