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Shop Smoak, since he still has some upside (presumably). But it more depends on if you think you'll get enough in return. Sometimes the best trade strategy is not to trade at all. Hold on to guys if you believe what you'll get in return won't amount to much WAR if you're in a playoff chase. You will have to do a lot of trade work to get a minor league contract prospect for Smoak, but you could bundle one with a middling ML contract player if you find the right trade partner.
Other than that, just remember not to trade away a veteran with good leadership traits for someone who isn't a leader. Also, if a player has high intelligence, work ethic, and leadership, keep him on the roster even if he's not currently producing.
Finally, you might have to over-pay Kendrys to stay on the roster beyond this year, which sucks, so just take a close look at your team's finances for the next couple of seasons to see if any other players are must-sign guys (like Nick Franklin). Also, remember that the M's owner, Yamauchi, is "generous", so as long as you meet your season goal, you'll get a budgetary increase for next season, so you have some wiggle room.
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