Buy, sell or hold? How to make sense of MLB's trade deadline

By Ben Verlander
FOX Sports Baseball Analyst

The days leading up to the MLB trade deadline can be weird, chaotic and downright confusing for fans.

"Why is our best player getting traded?"

"Why are we waiting so long to trade players?"

"Why are we sellers and not buyers?"

"Why did we get such a weak return on a great player?"

I’ll explain it all.

The deadline is Friday at 4 p.m. ET, and the days leading up to the deadline are usually among the most exciting of the entire season. 

In recent years, some deadline-week deals played huge roles in a team winning a World Series.

There are two recent trades that come to mind for me. One was in 2016, when the Chicago Cubs acquired closer Aroldis Chapman to lock down the back end of their bullpen. The other was a year later, when the Houston Astros acquired ace Justin Verlander before their playoff push and eventual World Series championship.

That’s why you do it. You commit to going for it. You commit to getting a World Series ring. 

How does a team decide to buy or sell?

Decisions at the deadline can make or break an organization for years to come. In the weeks leading up to the deadline, the talk starts about who will be buyers and who will be sellers. The trickiest part is that sometimes the teams themselves don’t even know until the very last day. 

The main reason for this is where teams are in the standings.

If a team has even a glimmer of hope of making the playoffs, it will hold out until the very last day to make a decision on whether to acquire new players and trade away prospects, or whether to trade away top players and acquire good prospects for the future. 

Let’s use the Washington Nationals as an example.

The Nationals have multiple players who would be huge assets to other teams down the final stretch of the season. Of course, those guys are also vital to the Nats' success.

Coming into this week, the Nationals were 6.5 games behind the first-place New York Mets. 

Let’s say the Nationals went on a little winning streak this week while the Mets struggled. Washington could suddenly find itself only a couple of games out of first place. Next thing you know, the Nationals go from sellers to buyers.

That’s not what is happening this week, however. 

The Nats have lost five of their last six games, pushing them down to fourth place in the division and 8 games out of first. Guys like Max Scherzer and Trea Turner are looking increasingly likely to be dealt, but the Nationals have still waited until the final days just in case things changed.

Complicating matters for Washington is a COVID-19 outbreak, which forced the cancellation of Wednesday's game against the Philadelphia Phillies.

Why is my favorite team trading our best player?

The answer to this question can be complicated.

First and foremost, it’s important to note that baseball isn’t a sport in which one player can get you into the playoffs and win you a championship. Mike Trout and the Los Angeles Angels are proof of that.

Secondly, it’s important to look at contracts. 

A lot of times you will see star players, even franchise players, get traded at the deadline when they are in the last year of their contract. Look no further than names like Trevor Story of the Colorado Rockies, and Kris Bryant of the Chicago Cubs. Both are franchise players. Both are on struggling teams. Both are in the last year of their contracts.

And both are likely to be traded because they are heading toward free agency and could attract more money elsewhere. So it makes sense for their teams to trade them now and get something back in return.

Story and the Rockies are a perfect example: He's one of MLB's best shortstops on one of MLB's worst teams. It's highly unlikely he'll re-sign with Colorado. There are several contenders who could use a shortstop of his caliber to push them over the hump. So the Rockies field offers and determine what they think will help them the most in years to come.

That’s what the trade deadline becomes: a battle of wanting to win right now vs. setting yourself up for the future.

Why did we only get THAT prospect in return?

The answer here is quite simple: If a player being traded is on the last year of his contract, he is essentially a "loaner," and teams don't like parting with top-tier prospects to "rent" a guy for only a few months. 

Players under contract for more than just the remaining season are far more valuable and will garner a much greater return.

A good example of this would be a player like slugging outfielder Joey Gallo.

Gallo is one of the top players on the market and is under contract through 2022. That's why the New York Yankees are sending four prospects to the Texas Rangers to acquire Gallo. He brings a bigger haul since the Yankees will have him under control for more than just this season. 

Buckle up. It’s trade-deadline week.

You can never fully understand the MLB trade deadline. 

It’s a chaotic week, and by the end of it, your team could very well have added one of the best players in baseball, or, your team could look like a skeleton of what it did the week prior.

Some lucky team could very well make a move that will lead to a championship.

So keep your eyes peeled. The future of your favorite team is being carved out now.

Ben Verlander is an MLB Analyst for FOX Sports and the host of the "Flippin' Bats" podcast. Born and raised in Richmond, Virginia, Verlander was an All-American at Old Dominion University before he joined his brother, Justin, in Detroit as a 14th-round pick of the Tigers in 2013. He spent five years in the Tigers organization. Follow him on Twitter @Verly32.