Baseball season is here again, so it seems a particularly appropriate time to ruminate on this subject.

As a native New Yorker and a lifelong Yankees fan, I never thought I'd see the day I'd be pulling for the Chicago Cubs to win the World Series. But last year, when the Yankees' season ended prematurely, I decided - having spent the past decade in Chicago, witnessing firsthand the ongoing frustration associated with supporting the North Side's lovable losers - it was time to lend a little moral support to the Cubbies.

And 2008 really seemed to be the year. The Cubs were the National League's best team, boasting a strong blend of hitting and pitching, not to mention a former Yankee in the manager's seat. They rode this talent to an impressive 97 wins (the team's most since 1945), and had eight players named to the All-Star team.

More significantly yet, it was exactly 100 years since the Cubs had last raised the championship banner. I, like millions of others, thought their time had finally come.

Sure, I had observed a few moments of glory sandwiched between countless instances of Cubs ineptitude, including the celebrated 1998 home-run campaign of Sammy Sosa and the 2003 team that came so tantalizingly close to advancing to the World Series against my Yankees.

This time, they were really due, especially with both the Red Sox (2004) and White Sox (2005) having recently put an end to their own longstanding championship droughts.

But then again, these are the Cubs we're talking about.

After a sizable pre-playoffs rally, which included politicians and former players, the Cubs laid an egg. Three games (the first two at home), three losses - with a combined offensive (read: repulsive) output of six runs.

That I was not crestfallen after this most recent debacle is certainly to be understood. After all, despite the fact that I was rooting for the Cubs, I was in no sense invested in their success. What surprised me, however, was the generally tepid response from their fans throughout the city.

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Following the sweep, reporters traveled throughout Chicagoland to capture the reactions of Cubs fans. I expected to read and hear comments from angry, frustrated people. In truth, though, I did not perceive any virulent anger. Rather, I picked up on three other, more moderate reactions - one somewhat negative, one neutral and one more positive.

The negative sentiment was expressed by the non-believers - those Cubs fans who had tasted disappointment for so long that they could not permit themselves to truly expect anything other than failure. By lowering their expectations, they would be able to shield themselves if and when history would in fact repeat itself. This "I knew they'd lose" defeatism was expressed by many among the Cubs faithful.

Others reacted with blasé indifference. These were the fans attracted more to the baseball cathedral known as Wrigley Field than to the team it plays host to. In their eyes, Wrigley is a monument unto itself, where the game becomes secondary to the venue.

Lose as often as the Cubs have and you can understand why an unofficial mandate of eat and imbibe began to permeate so long ago. Why else should one leave work early on a sunny August day and head down to the ballpark? It certainly makes bad baseball far more tolerable.

The third group, on the other hand, responded with a healthy dose of optimistic persistence. These people understood that all was not lost; they would simply "get 'em next year" (the Cubs' unofficial motto). Sure, they were disappointed with the team's performance, but they refused to allow themselves to get excessively down about it. After all, is there really much of a difference, in the grand scheme of things, between 100 and 101 years of waiting?

As I was processing all of this, it dawned on me that in some very basic respects these responses mirrored the range of reactions among Jews regarding something far more significant that we have long been awaiting - namely, the coming of Mashiach.

There are times when we can be moderately negative about the imminence of Mashiach's arrival. Certainly there are no believing Jews who are not completely resolute in their conviction that he will eventually come.

The most famous and commonly repeated principle in Rambam's list of fundamental Jewish beliefs states, "I believe with a complete faith in the coming of Mashiach. And even if he tarries, every day I await his arrival." Every trusting Jew embraces this concept.

But the idea of Mashiach coming imminently, as in today, can often seem as far removed as a Cubs championship, if not farther. Consider this, from Rav Shimon Schwab, who recounted his youthful perspective on the idea of Mashiach:

As well as this, from the Chofetz Chaim, quoted by Rav Schwab:

If this lack of emunah was perceptible in the more spiritually attuned world of pre-war Europe, certainly it would appear to be a challenge for us as well.

The problem, however, runs even deeper. Not only are we often skeptical about the imminence of Mashiach's arrival, we may at times be entirely indifferent, if not moderately hostile, toward it altogether.

We surely all intellectually long for the Messianic Era. How could we not? Even the relatively naturalistic view of Rambam (Commentary to Sanhedrin 10:1) paints a picture of such glory that we cannot help but yearn for its imminent arrival:

Yet at times I wonder whether these promised spiritual and material gains sufficiently motivate the average Orthodox American Jew to remain excited about the prospect of completely changing his current realities, including his comfortable lifestyle.

Let's be honest. We enjoy more opportunities here in America than Jews have ever experienced in any other country in the Diaspora. We walk the streets largely unafraid. We can pray in public places and even secure police protection on our holidays. We possess our own extensive media outlets and educational systems, unimpeded by sinister, meddling governments.

Materially, we are as well off as we have ever been; Jews have tasted great success in practically every form of business imaginable. Even in today's troubled economic climate, with all the difficulties individuals and institutions are being forced to endure, we are far more affluent than ever before.

Certainly, in this context, it is quite a challenge to remain enthusiastic over the idea of Mashiach's arrival, which threatens to drastically challenge our status quo. Again, in the words of Rav Schwab: "If I really believe that [Mashiach] can come any day and I need a house, I won't build a luxury house, for who knows how long I would be in that house? How can those who build extravagant villas for themselves truly believe that at any moment he can come?"

For the average American Jew, life in this country has such an aura of permanence that it is often difficult to see beyond it and factor a different reality into our long-term plans.

Thankfully, and almost paradoxically, we are also blessed with a healthy dose of optimistic persistence. Despite the long wait, and the immeasurable suffering we have had to endure, we have never lost hope in a better tomorrow.

It is one thing to wait one century for a World Championship. It is a far greater challenge to wait nearly twenty times that period for the most wonderful historical outcome imaginable, only to endure setback upon setback, suffering upon suffering, exile upon exile.

Yet we have done just that. And the very fact that we continue to long for the arrival of Mashiach is a powerful indicator that our belief in his coming remains strong.

We know from our tradition that Hashem bestowed upon us the special gift of forgetting, in order to allow the pain of loss to gradually dissipate and permit us to properly redirect ourselves toward the future. This only occurs, however, when the object of our sadness has in fact moved on to the next world. If the person for whom we grieve is still with us (even if we are unaware of it), the special gift is not granted and we remain in perpetual pain and agony.

In the words of our sages (Talmud, Pesachim 54b), "No one accepts consolation for a person who is really alive but believed to be dead, for it is decreed that a dead person should be forgotten from the heart, but not a living person." It is through this idea that we can understand why Yaakov Avinu was unable to achieve any meaningful degree of comfort in the more than two decades that followed the assumed death of his beloved son Yosef (see Bereishis 37:35 and Rashi, ibid.).

In a similar vein, we refuse to be consoled for the loss of our beloved Bais Hamikdash. Though it appears "dead" (God forbid) to the outside observer, we know that it is very much alive in the hearts and minds of the Jewish people. It is for this reason that we hold out hope for its speedy return.

Despite our strong desire for Mashiach's arrival, however, we must be careful not to become impatient. He will certainly come, but on his terms, not ours. As the Talmud (Sanhedrin 97b) teaches us, "[the coming of Mashiach] depends solely on repentance and good deeds."

This idea helps explain an apparent Talmudic paradox with regards to the very idea of yearning for Mashiach's arrival.

On the one hand, the Talmud (Shabbos 31a) informs us that one of the six questions we are asked by the heavenly tribunal immediately after our passing is "Did you eagerly hope for [messianic] salvation?"

But another source (Sanhedrin 97a) suggests we have no such obligation to long for Mashiach, and that in fact, "[Mashiach] will not come unless the Jewish people have given up hope for the redemption".

What exactly does this latter statement mean and how are we to resolve this apparent contradiction? Are we supposed to long for his coming or are we not?

The answer is that we certainly are supposed to continuously yearn for the coming of Mashiach. Failure to do so can be disastrous, to the point of possibly impeding our entry into Olam Haba.

When the Talmud says we must give up hope for the redemption, it means we must give up hope of bringing Mashiach on our terms, without taking the necessary steps to truly deserve it. That is what the other Talmudic statement means when it says repentance and good deeds are necessary prerequisites for his coming.

We must, however, realize that this level of character improvement can come in one of two ways. We can repent on our own, or Hashem may choose to step in and expedite the process by bringing in an outside motivator, as the Midrash (Tanchuma, Bechukosai 3) makes clear: "If the Jewish people do not repent from their own volition, the Holy One, blessed be He, will cause to rise against them a wicked king whose decrees will be as cruel as that of Haman. He will subjugate them, and consequently they will repent."

This is what the Talmud (Sanhedrin 98a) means when it says, "the son of David will come only ina generation that is either altogether righteous or altogether wicked." When the time is right Hashem will take stock of His people. If we are righteous, we will certainly merit his coming. If not, Hashem will take the necessary steps to ensure our readiness, thus clearing the path for Mashiach.

Contrary to the belief of some, we have no control over when Mashiach will actually come. The only thing we can impact is our spiritual state at the time of his arrival.

And a sizable portion of that readiness involves our general sense of focus and longing for his arrival. If we are truly waiting - if, like the Chofetz Chaim, we leave our suitcases by the front door (as the great sage did in eager anticipation of Mashiach), we will hopefully merit to reach the degree of righteousness that will allow us to be ushered directly into the Messianic Age, without any of the difficulties described above.

Once more, the words of Rav Schwab: "Waiting is of the essence. When we wait for him, something happens to us. It elevates us, for we want to be prepared for his coming."

Let us hope that in the merit of such anticipated waiting Hashem will finally put an end to this long, difficult exile and return us to our truly desired state, speedily in our days.

If we are still here, though, a Yankees-Cubs World Series in October would be nice.

Rabbi Naphtali Hoff, M.Ed., is an instructor of Jewish history at Hebrew Theological College (Skokie, Illinois) and serves as associate principal at Yeshiva Shearis Yisroel in Chicago. More information about Rabbi Hoff can be found at www.rabbihoff.com.