The Jays have backed themselves in to a corner with no good way out.
They didn't trade Bo when his value was high, yet didnt make an attempt to re-sign him either. Didn't re-sign him when his value was low - and now he's on the doorstep of free agency and will get paid more than what he is worth to the Jays. The only solution left with Bo is to trade him - but his value is lower now coming off a poor season and only having 1 year of term left.
With Vladdy - I think they thought they were being smart playing the waiting game, but its becoming more and more likely it will come back to haunt them. He is in good shape now and just had a monster season. He will likely earn a large contract and this close to free agency - he will be very tempted to test the market and shop himself around. He may end up back with the Jays but at a massively inflated price tag.
Just really really poorly done by Shatkins.
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