Pessimist – Lack of “Big-Name” Prospects
There is no question that Mark Shapiro and Ross Atkins have done an admirable job in restocking the farm system that Alex Anthopolous gutted out. However, the lack of multiple “Big-Name” prospects, such as a Yoan Moncada or an Andrew Benintendi, should worry both the front office and fans if the Blue Jays decide to pursue a rebuild. There is arguably only one top prospect in the Blue Jays system and that is Guerrero Jr., who himself is a borderline top prospect due to his young age and relatively limited experience.
Taking a look at the Cubs or Red Sox as an example, the path to success was led by a boatload of top 30 prospects. Think Betts, Bogaerts, Benintendi for the Red Sox and Bryant, Rizzo, Schwarber, Russell (etc, etc.) for the Cubs. As the Jays lack multiple potential superstars, the front office will have to either nail trades involving veterans like Estrada and Happ or hope that some of the current prospects really take a big step forward in their development.
It is also important to consider that players like Pillar, Sanchez, Stroman and Osuna will only be a few years from free agency at that point so even if the front office manages to surround them with a winning roster, another continuous retool may be in store in 4-5 years.
Another caveat to the rebuild idea is that some of the Jays top prospects have their flaws and may not pan out. For example, while players like Alford, Urena, and Greene have tantalizing potential and could develop into above-average major league players, their minor league careers so far have been extremely inconsistent and it is not unknown for prospects to become busts in a very short period of time.
Although the rebuild idea could appeal to those seeking a brighter future that is similar to where the Cubs and Red Sox are right now, the safer option for the Blue Jays is likely the continuous retool process. That way, the management can keep the fans (and bandwagons) interested with “name-value” veterans while quietly stocking up young talent through small trades and successful drafts.