Pre-Deadline Trades the Blue Jays Should Consider.

Whether the Jays want to make roster tweaks for next year or blow up the team and start again, Josh Higgs takes a look at a few trades the Toronto brass need to consider.

JOSH Higgs
The Ocho
6 min readMay 23, 2017

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This season began with optimism, despite the lingering heartbreak of the offseason.

Gone was Edwin Encarnacion, the Jay’s beloved power hitting first baseman. However, coming off the heels of yet another AL division series loss, expectations for a successful season in Toronto were high.

Then the regular season began, and reality sunk in. This Jays team wasn’t on the level of the playoff-calibre teams from the past few years. They began the season 8–17 in the month of April, not winning their first series of the season until the end of the month.

The team has managed to stem the bleeding. They’ve won eight of their last 10, bringing the team to 17–21, four games below .500. That said, injuries have bitten this squad everywhere.

Josh Donaldson, J.A. Happ, Troy Tulowitzki, Russell Martin, Francisco Liriano, and Aaron Sanchez have all spent time on the Disabled List. Losing all of these star players was a huge part of their poor performance in April.

It isn’t surprising that the Blue Jays faltered so greatly when half their gameday roster belonged on the AAA Buffalo Bisons. That said, it seems to be a matter of when, not if, the Blue Jays decide to re-tool. The biggest decision facing the Blue Jays brain trust of Ross Atkins, Mark Shapiro and Co is whether this is a complete tear down or an attempt to refit the roster to compete again next season.

Below are a list of trades the Blue Jays could or should make to propel the team to a brighter future.

Likely to be traded

1. Jason Grilli / JP Howell

Both guys were brought in to help fix the leaky bullpen, and both are unrestricted free agents (UFAs) at seasons end. Both have struggled mightily this season, but veteran bullpen presence is a valuable commodity. I’m sure there will be some team with interest, but the return will be nothing but a low level prospect, and the Jays may have to eat a bit of their contracts.

2. Joe Smith

Another free agent signee this past off-season, Smith has been playing lights out. Sporting a 2.57 ERA, a 1.14 WHIP, and 13.29 K/9, he will undoubted be sought after come the trade deadline July 31st. Smith also has closing experience from other squads, which in some teams’ minds actually means something. Teams like Washington, Texas, St. Louis, and Colorado (if they remain a legitimate threat) could all trade for his services to help bolster the back end of their bullpen.

PREDICTION: St. Louis for (82nd ranked prospect) infielder Delvin Perez.

3. Francisco Liriano

A veteran lefty on the final year of his deal, he’s pitched well this season besides two outings: his first start and his last start prior to hitting the DL. A playoff contending team looking for added depth at the end of their rotation will surely be interested. Look for the Yankees, Cubs, Red Sox, Orioles, Red Sox, Astros, Rockies, or Rangers to put forward offers.

PREDICTION: Chicago Cubs for pitcher Oscar De La Cruz (5th ranked in Cubs system).

Unlikely but possible

4. Marco Estrada

The soft tossing fly ball pitcher with a filthy changeup will no doubt garner plenty of interest. Although he’s recently stated he wishes to return to Toronto, they’d be crazy not to gauge his value. A myriad of teams could use an anchor like Estrada to solidify its middle rotation. Interested teams could include: NY Yankees, Boston, Baltimore, Houston, Texas, LA Angels, Colorado, Arizona.

PREDICTION: I think he stays, but Houston is a long shot, as they need rotation help. They could move the towering pitcher Forrest Whitley (76th overall prospect).

5. J.A. Happ

The Milk Man is under contract for this and next season, so there isn’t a dire need to consider moving him. That said, the price will be steeper the longer his contract is (see Chris Sale trade), and his contract is very team favourable. Teams interested in the lefty would have to give up a larger prospect package to fetch him, and likely an MLB ready starter. Teams that could be interested are: NY Yankees, Baltimore, Houston, Texas, LA Angels, NY Mets and Colorado.

PREDICTION: He will stay this year, but he could be dealt in the offseason. If the Jays are bad next season, he’s gone by deadline next year. If he is moved, a team like the Mets might be thinking ahead about life after Matt Harvey. They could offer pitcher Robert Gsellman and pitching prospect Justin Dunn (3rd in Mets system).

Long shots

Say is ain’t so, Josh!

6. Josh Donaldson

The face of the franchise is under contract until the winter of 2018, but if traded, it would signal a full rebuild for the Jays while also netting them a king’s ransom of prized prospects.

It seems likely that he will walk after the 2018 season for greener pastures, as he will undoubtedly command a contract in excess of eight years and 200 million, which Toronto is unlikely to offer. Furthermore, if he walks, the Blue Jays’ compensation will likely be only a second and fifth round pick at best thanks to the new collective bargaining agreements rules on free agent compensation.

He will be a part of a free agent class that includes Manny Machado and Bryce Harper, so teams will be looking to spend. Donaldson would be an attractive option for Boston. Other teams that would be interested (and could afford such a hefty contract) would include LA Angels and The New York Yankees. The Tigers could free up approximately 46 million in the next two years, and could conceivably make a run at Donaldson if they haven’t still learned their lesson about signing big name free agents to mammoth contracts. The San Francisco Giants could also be interested as they’ll free up a lot of money from Matt Cain’s awful contract.

The two teams that might have the most interest, as both a free agent and in the trade market, are two NL East rivals in the Atlanta Braves and Philadelphia Phillies. Both are rebuilding, and while they are a few years from contention, their farm systems are bursting at the seams with prospects, and they have plenty of money to burn.

PREDICTION: Josh Donaldson signs with Philadelphia for seven years and 210 million in the winter of 2018. If Philly were smart, they’d snag him this offseason via trade, possibly for outfielder Mickey Moniak (16th ranked prospect, 1st overall pick in 2016), pitcher Mark Appel (former 1st overall pick in 2013), outfielder Roman Quinn and pitcher Sixto Sanchez (6th and 7th ranked prospects in the Phillies system).

Virtually untradeable

7. Jose Bautista / Russell Martin / Kendrys Morales / Justin Smoak / Troy Tulowitzki

The following players were grouped together for having either gargantuan contracts (Martin has three years and 60 million remaining, Tulo has four years and 74 million, Morales has three years and 33 million), no skill (Justin Smoak), or no market (Jose Bautista).

All of these players are on the wrong side of their prime years, have lengthy injury histories, and are declining both offensively and defensively. Some have options that won’t be picked up, but those above numbers are what is guaranteed on their contracts. That being the case, they will be virtually unmovable to any team, unless the Jays agree to eat a significant portion of their contracts.

Josh is a baseball contributor for TheOcho.ca. By day he teaches in schools or works at gas stations. By night he’s watching hours of sports and brainstorming his next article.

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JOSH Higgs
The Ocho
Writer for

University graduate, teacher, Sports guru, sabremetrician, and fantasy player. Specifically in baseball, wrestling and collegiate sports.