Blue Jays trade deadline: How much do you want to bet?

As it currently stands, the Blue Jays sit in a strong position going forward in another attempt to make a playoff run. At just 2.5 games back of the Baltimore Orioles, with a far better run differential, the Jays will almost assuredly compete throughout the rest of the year to repeat as division champs or, at the very least, get a chance at one game free-for-all with a playoff berth on the line.

With that said, the time has come to ultimately decide if the Jays need to make any upgrades to their current roster at this year’s non-waiver trade deadline. Currently, the shopping list is fairly simple: the Jays would or should like to add a little bit of depth at the starting pitching position—we aren’t talking about a David Price upgrade but someone other who can take the ball in the event of a long-term injury or a Aaron Sanchez shutdown—and a reliever in the Jays bullpen. Of course, with any trade or gamble really, you have to put something down on the table yourself. No one goes to Vegas and walks away with free money. It doesn’t work that way.

So the question is, what are you willing to gamble with. What are you going to walk into the casino with and walk home without? Last year, it was a slue of top prospects. It started with top prospect Miguel Castro, Jeff Hoffman before dishing out a package of other pitching prospects that included top prospect at the time, Daniel Norris. I’m not going to use thousands of words to argue that any of those moves were misguided and a waste of prospects because they weren’t. The Jays took a shot at glory and missed. That’s life sometimes.

However, after gutting the system of 10 pitching prospects, it’s hard to argue that it would be a good idea to do it again with a weaker crop on the farm. Prior to the season, the Blue Jays farm system was ranked by Baseball Prospectus as the 22^nd best in the league and 24^th best by MiLB. Take your pick, it wasn’t good. Despite that, strong seasons from meandering prospects like Sean-Reid Foley and Max Pentecost have, in my opinion, likely improved that system to be more closely characterized as middle-of-the-pack. This also doesn’t mention the strong starts by Vladimir Guerrero Jr. who’s hitting .238 in Bluefield with two-home runs and Jon Harris who’s nearly implicitly demanding a promotion from Lansing after owning a 2.50 ERA through 72 innings pitched.

The best way to define Toronto’s farm system though would be to say it’s bottom heavy. With the exception of Rowdy Tellez and Conner Greene (who’s thrown just one start in New Hampshire) not a single one of Toronto’s top 10 prospects are playing beyond Single-A level baseball. There’s nothing wrong with that either. The ceiling on some of these talents is definitely still palpable and lofty. However, the value, on the open trade market, is significantly lower for these types of prospects compared to a mid-level prospect who organizations are much easier able to scout and determine the viability for in a trade.

Thus, if the Jays are looking to add a viable piece through the trade market, they’re likely going to have to package some of these top 10 prospects and gut the system once again, which may not be a good idea. With each day, Edwin Encarnacion, Jose Bautista, Michael Saunders and others walk closer to free agency, leaving the Jays roster with gaping holes emblematic of the Toronto Maple Leafs defense. At some point there is going to be a time when those prospects have to fill those holes on the Jays’ roster. If you trade them away now, and aren’t able to re-sign any of the aforementioned stars to long-term contracts, the situation north of the border could get dire in a hurry.

Approaching the All-Star break is the perfect time to reflect on the organization as a whole before you enter into the gambling ring. Take stock of your assets. Measure what you’re willing to gamble with and prepare yourself rationally to walk into the trade market and say no if the asking price is too high.

Certainly, I agree that if the price is right, as Bob Barker would say, make the trade, gamble a little bit and try to beat the dealer. But we have to remember that this gamble can come at a significant cost too. Laying the chips down on the table in hopes of winning big can be one of the most enlivening, exhilarating feelings in the world. It’s what brings us back to the table repeatedly in the first place.

But it can also be the most damaging as well. It depends how much you're willing to gamble. How close you're willing to fly to the sun. Try to remember that.