This is similar to how I feel. One thing I would add is that when you get to a level where you are competing for the very best players with the best clubs, it requires a different level of patience. These are the kinds of players everybody else wants and the selling clubs are desperate to hang on to them too. Think about De Gea to Madrid situation last year from the perspective of a Madrid fan – how gut-wrenching of an experience it must have been, to anticipate this transfer all summer, follow every twist of the the protracted negotiations until the last day of the transfer window, and then see it all fall apart on a technicality... And that's the richest and most desirable club in the world (and the most spoiled fans) we're talking about! But that's the kind of transfer sagas the biggest clubs are used to, because that's what it takes to sign the most desirable players.
My sense of Klopp's strategy is that he certainly has contingency plans in case VVD and Keita signings don't work out. I think VVD one is more crucial, because we definitely NEED a central defender, so I don't think we can wait too long on this one – if Saints make it clear they won't sell, at some point we'll need to move to the plan B or C (I think Keane was likely the plan B, so probably it's going to be plan C or D – that's the price you pay for waiting). With Keita, I really think this is more about improvement rather than plugging a clear weakness in the team – so if it doesn't happen this summer, I think Klopp possibly won't go for a similarly high-profile signing in midfield and will just wait until Keita's release clause kicks in next summer. I suspect this one could go to the wire. It's a tense situation, but on the other hand Klopp can afford to be fairly relaxed about this too, since there is not much we can do at this point except to give the selling club and the players in question some time to test each other's resolve and hopefully accept the inevitability of the sale.
Finally, on the LB front, I suspect the reason we haven't signed Robertson yet is because there is another player we think we could potentially get and we don't want to give up that option by committing to a signing now. I have no idea who that player might be, but sometimes things have a domino effect, like when a big club makes a signing and then a player who is being replaced (who could still be an excellent player) and who wasn't available until now, becomes available. That happens pretty often – for instance when Barca sold Maxwell to PSG after they got Mathieu, I think – and that's why in some cases it's advantageous to wait until later in the window when a few of those domino chains get started.
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