‘Tis the season to ponder massive contracts, as teams and free agents attempt to balance how much money there is to give, and how much there is to take.

Baseball is at a fascinating historical juncture, as we continue to see the largest deals in the sport’s history eclipsed – ten of the 12 largest deals in terms of total money have been signed since 2012 – just as we see many of the previously staggering long-term, big money deals expire.

Ultimately, these massive deals hinge on the value generated, although the return on investment over the life of a long-term contract can be hard to evaluate in a satisfying manner, even given new analytical tools.

It’s difficult to look at any of the recently-lapsed deals and label them as unqualified successes or failures. In most cases, teams were well-served by the players for a portion of the contract, but not for the entirety.

Take Mark Teixeira’s recently completed eight-year, $180 million contract. Is 20.6 WAR (per Baseball Reference) an adequate return? Does the eternally-flying 2009 World Series flag mitigate for the fact that he had three seasons of 1.0 WAR or less in the last four years of that deal?

But then, if you pair that deal at various points with the declining years of Derek Jeter, Alex Rodriguez, C.C. Sabathia, and Jacoby Ellsbury, you can see how even big budget teams’ offseason exuberance can eventually catch up with them.

The anxiety for fans stems from the degree to which an ill-advised contract will leave a team hamstrung, and unable to make up the difference between the value paid versus value returned. Up until recently, it was supposed that only the top two or three payrolls could withstand a bad contract, let alone multiple bad deals.

For Blue Jays fans, contemplating a large contract for either of their aging sluggers needs to be buttressed against the knowledge that they have the back end of two large contracts due over the next few seasons. If Troy Tulowitzki and Russell Martin trend downward in the next three seasons, how essential is it to ensure that a large contract for Edwin Encarnacion or Jose Bautista is worth the money?

At the same time, with a larger payroll for the Blue Jays, more money in the sport in general, and the majority (18) of teams carrying payrolls over $100 million last season, there seems to be more latitude to succeed despite bad money on the books.

Even with a general valuation of $8 million per Win Above Replacement, there’s no shortage of bad deals or dead money found on 2016 playoff teams. The Red Sox received -0.2 WAR for their $17.6 million dollars spent on Pablo Sandoval, and 0.0 WAR for the $11.3 million spent on Rusney Castillo. David Price ($30 million, 3 WAR) and Clay Buchholz ($13 million, 0.2 WAR) were also poor investments, while Hanley Ramirez ($22.75 million, 2.8 WAR) barely passes muster.

Elsewhere in the AL East, the Baltimore Orioles received questionable returns on the $16.33 million paid to Adam Jones (1.1 WAR) and Ubaldo Jimenez ($13 million for 0.1 WAR), while deals for for Matt Wieters ($15.8 M for 1.7 WAR) and Chris Davis ($21.1 M for 3.0 WAR) look precisely like the sort of contracts that continue to inflate the cost of a single win. But one should expect that the premium paid on these massive deals would account for those elusive All-Star calibre WAR figures over 5.0, with each additional win increasingly valuable and scarce.

The Texas Rangers played to the best record in the American League, all while carrying $18 million of Prince Fielder’s deal and getting -1.4 WAR in 89 games before he was forced into retirement. Also, Shin-Soo Choo’s $20 million returned just 0.3 WAR.

Despite all that bad money, those teams were all buoyed by the success of their younger, controllable and inexpensive players. Boston’s success occurred because of huge seasons from players making less than a million dollars, including Mookie Betts (9.6 WAR), Jackie Bradley Jr. (5.3), Xander Bogaerts (3.7) and Steven Wright (2.1), each of whom earned less than $650,000.

The Orioles paid just $5 million for the 6.7 WAR delivered by perpetual MVP candidate Manny Machado, and had a trio of pitchers post WARs above 4.0 while earning $6.75 million (Zach Britton), $6.225 million (Chris Tillman) and $532,000 (Kevin Gausman).

The Rangers managed to squeeze marginal value out of a number of bargains, including Rougned Odor (2.4 WAR) and Sam Dyson (2.9 WAR), each of whom received for $522,000 for their efforts.

So teams can succeed when multiple veterans don’t live up to their contracts. But before anyone breaks out into a hoary chorus of “Pay the man!”, consider Josh Hamilton.

Hamilton cost the Rangers just $2 million this season, so the fact that he didn’t play a single game was of minimal consequence. But for the Los Angeles Angels of Anaheim, Hamilton was their highest paid player in 2016, with a $26.4 million salary. Add to that the $25 million for Albert Pujols (1.4 WAR), C.J. Wilson’s $20.05 million for zero games pitched, and Jered Weaver’s $20 million, -0.7 WAR-season, and you can see how a big money team can get into big trouble.

Aside from MVP Mike Trout, only one other Angel (Andrelton Simmons) managed to generate 4.0-plus WAR.

On the other side of the spectrum, Cleveland didn’t pay a single player more than $8.45 million (Carlos Santana, 3.0 WAR), which was less money than Anaheim doled out for aging closer Huston Street. And even the deadest money on Cleveland’s roster – $15 million worth of Nick Swisher and Michael Bourn regret – wasn’t so bad comparatively speaking.

At present, the Blue Jays’ payroll isn’t overly weighted with bad contracts. Not yet, anyhow. The question for Blue Jays fans as they look ahead into this offseason is: How solid is the young talent base if the expensive veterans don’t produce? How many more deals that under-perform or bottom out can they take on before that financial equilibrium is tipped?

Moreover, how much should the Jays be willing to invest in any hitter when the only position player in the top 10 in WAR who is currently on a big money deal signed in free agency is Robinson Cano?

It’s true that a budget that could peak around $160 million could afford some dead money. But the Jays need to feel sure they have the inexpensive depth to counterbalance expensive veterans offering diminishing returns.