The Thrill and Agony of Going All-In

While more than half of the MLB regular season remains to be played, the time has already arrived for many fantasy owners to decide whether they should continue making improvements at the margins or gamble with a major trade.

I'm not talking about the one-for-one swaps of solid players, though those can exert quite an influence themselves depending on what our favorite random number generator spits out. Today, we're pondering the kinds of deals that are immediately obvious as seismic shifts to the rosters involved, as forks in the road that was the 2019 season. It might be for reasons of quantity (trading five players at once will certainly alter the complexion of your team) or quality (though they are rare, instances where it makes sense to trade Mike Trout do exist).

Even if you're not thinking about a move like this right now, many of you will be eventually - some sooner rather than later. If and when you reach that point, here's an cold, clear-eyed appraisal of the enterprise.

Stay the Course, Or Risk It All?

It's the principle behind countless games, from poker to Jeopardy!: How much are you willing to bet that you're right? If you don't know, you haven't given the question enough thought. Questions, plural, would be more apropos, as there are several sub-questions to consider to arrive at a well-considered conclusion to the topline query.

First and foremost, is a drastic move truly necessarily, or emotionally motivated? I'm as tired of watching Jose Ramirez go 0-fer as anyone else, but in the one league where I own him, I've managed to navigate my way into first place through Thursday's action. It's also a keeper league in which he priced reasonably enough that a rebound would render him an attractive asset. This is an obvious and fairly painless "hold and hope", given the circumstances. If you are languishing in the standings after drafting JoRam in the top 3, as is the more likely scenario, it may be that the best time to trade him has already passed. On the other hand, if you're staring up at the rest of the league for other reasons, the potential of a return to form in the season's second half may make him an ideal trade target.

There are less extreme examples, of course. Generally, it's helpful to try and place yourself in a rival's shoes when evaluating a player who's been frustrating to own. After all, that's why buy-low opportunities usually exist in the first place; if you've lost patience with a player who can't seem to break his slump or stay out of the trainer's room, you're naturally going to be more amenable to giving him up in a trade. It's okay and inevitable to experience frustration, but it should force your hand as seldom as possible.

What might help that is thinking through the second question: What's your plan of attack? Are you buying low on big-name guys who have been ineffective or injured for another owner who may not have read the previous paragraph? Perhaps you're in a position to consolidate talent by trading multiple good players for a great one, or sell off cheap keepers for high-priced talent. (More on that in a moment.) Maybe you're flipping an established player who's been underperforming for a guy who's looked great in the last three months but at no other point in his career. Could be you're trading from a strength to shore up a weakness, or writing off a category entirely in a bid to make gains in other areas.

One of the most crucial influences on your strategy is question number three: How much are you prepared to borrow from the future for present value? Again, we must consider the circumstances. If a few good weeks would get you back in serious contention, it might not be advisable to mortgage the future. Unless, of course, you have observed your squad with a sober gaze and determined that they don't quite have what it takes you bring you a title without an infusion of talent. Then again, it also may not behoove you to package your cheap prospects and young MLB talent for a star if your roster is, in fact, too weak to push back into the race even with that player's service.

The last question we'll tackle today likewise flows from the one before it: What is your competition doing, and does it merit a response? You may already have been looking at the likely dogfight ahead and kicking around the idea of a risky trade when you get the notification that your biggest rival has made a splash. Oh, and look at that, the players they've acquired are specifically tailored to counter your advantages! In this case, assuming you've come to satisfying answers to the earlier questions, all systems are go for the kind of trade that might go down in the annals of your league's history as a seminal moment.

Gentlemen, the game is afoot. Remember that flags fly forever, but you can also make trades that haunt you for years. Good luck.

The Friday Meta is Kyle Bishop's attempt to go beyond the fantasy box score or simple strategic pointers and get at the philosophical and/or behavioral side of the game. It is hopefully not as absurd, pretentious, or absurdly pretentious as that sounds.

More Fantasy Baseball Analysis