The Angels are expected to try again to make Mike Trout a lifetime Angel when they discuss a contract this winter, and one rival agent suggested Trout’s agent would be wise to wait until free agents Bryce Harper and Manny Machado are signed to provide the floor.
Trout’s agent, Craig Landis, is experienced and may not need the advice, and he certainly has his focus on Trout now, mostly because Trout’s an all-time great and the best current player in the game, but also because he’s Landis’ lone prominent client at this point.
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The Angels, as was reported here, tried to sign him to an all-time long deal at the time they were able to compromise and form the $144 million, six-year deal through 2020. Trout is the highest-paid position player at $33.25 million this year and could be again the next couple seasons at the same rate, depending on what Harper and Machado get (and possibly whether the Angels re-do Trout's deal).
Anyway, Trout’s biggest concern seems to be to play for a winner after going to the postseason only one time in seven years with the Angels, and Shohei Ohtani’s Tommy John surgery is a blow for next season. However, by all other accounts, Trout seems to have loved his time in Anaheim (or Los Angeles, or wherever they claim to be) despite the fact there’s no weather there (Trout’s other main interest is the weather).
Though it’s a small sample size, Trout hasn’t been known as a holdout (he signed immediately upon his selection at the draft back in 2009 — he even attended the draft at MLB Network in his home state of New Jersey — and did do the one long-term contract with the Angels). But the advice here is to hold out, at least until Harper and Machado, the two best free agents position players in years, since Alex Rodriguez 11 years ago, sign their own deals this winter.