Talking to TSN 1050's Naylor and Landsberg Tuesday morning, ESPN Baseball Insider Buster Olney believes the Toronto Blue Jays had one of the worst lead ups to the trade deadline and squandered an opportunity to get the best value for some of their top players. 

"I gave them a D+," Olney said. "It was the fourth-lowest grade out of the 30 teams in baseball."

However, Olney said he believes it was the play of the players in the end that made things difficult on management and cost them on Monday. Pending free agents Marco Estrada, Francisco Liriano and Jose Bautista have all had poor campaigns this season, so their trade value dropped significantly from where it previously sat. 

"I don't really blame the front office for this, I think they were incredibly unlucky as we talked about it last week with so many of their pending free agents having miserable seasons which cut into their trade value," he explained. "But you can't get around the fact that you're not going to get much return when a Liriano is having a bad year, when an Estrada is having a bad year, when a Jose Bautista is having a bad year.

"That was absolutely devastating for them and let's face it, you get (Nori) Aoki with team control, helps you in the outfield but it's not that much of an upgrade and didn't change trajectory into 2018. That would have been your biggest goal heading into the trade deadline." 

Monday's deadline may have also been the best time to shop the likes of third baseman Josh Donaldson if the Jays were considering a full rebuild, but without a deal Donaldson's marketability may have taken a nose dive. 

"When it got to 4:01 (PM) yesterday, his marketability dropped probably 25-30 per cent," said Olney. "A potential trade return dropped significantly because he's one year closer to free agency and is one less year away where he could impact a pennant race. That happened with the Orioles and Manny Machado as well."

While talking with other teams, Olney says the impression they got was that Jays ownership did not want to go through a whole rebuilding cycle and potentially upset their fan base. In the long run, though, upsetting the fans now may have paid off in the future.

"I heard [Donaldson] talked about with other organizations, but the perception that they had was that Toronto's front office and ownership is very cognizant that they fill their ballpark every day and they weren't ready to go through a rebuilding cycle and talk about guys like Josh Donaldson and like Marcus Stroman," said Olney. "Baseball wise, that may have been the best way to go."

Olney, however, believes the Blue Jays might not be done with making moves. Marco Estrada could still be dealt before the waiver deadline at the end of August, with many teams including the Boston Red Sox and New York Yankees looking for pitching depth. 

"A team like the Red Sox, who started Doug Fister last night but he's been up and down, they would be a perfect potential landing spot [for Estrada]," he explained. "The Yankees, depending on how some of their young pitchers respond to the increasing number of innings, they could be a team that could make a waiver claim. All the teams that are chasing the Astros are going to have a shot at him before Houston does."

As for the Blue Jays' American League East rivals, Olney says while both Boston and New York have done great jobs to put themselves into a position to succeed, the Yankees appear to be in the driver's seat. 

"Three years ago the [Red Sox] had the best farm system in baseball and they have spent so many of the resources in their farm system," he said. "They've basically strip mined their farm system to get Craig Kimbrel, Drew Pomeranz and Chris Sale to make moves and put themselves in this position. They do have really young position players, guys like Mookie Betts, Rafael Devers, who has been terrific since being called up, they're going to around awhile.

"But within a year or two they're going to start having pitching issues."

"The Yankees on the other hand are loaded. They have completely rebuilt their farm system; they have terrific guys at the big league level who are young like Aaron Judge. They have two anchors now at the front of their rotation Luis Severino and Sonny Gray who are young. They made that Sonny Gray trade without either touching their number one prospect Gleyber Torres, who is going to be their shortstop for years in the future or their number two prospect Clint Frazier who has had an impact at the big league level already."