The Philadelphia Phillies have already been one of baseball’s most active teams this winter, making a significant trade with the Seattle Mariners to acquire shortstop Jean Segura and a pair of relievers, signing free agent outfielder Andrew McCutchen to a three-year deal, and recently inking lockdown reliever David Roberston to a two-year contract. For most teams, that is more than enough activity for one offseason.

But if this is it, Phillies fans will certainly be disappointed.

In November, Phillies owner John Middleton told Bob Nightengale of USA Today that the club was “going into this expecting to spend money…And maybe even be a little bit stupid about it.” However, he has yet to do so. While the Phillies have been connected to blockbuster free agents Manny Machado and Bryce Harper, they have yet to ink a deal with either superstar, and plenty of other teams are still competing for their services.

While Harper and Machado are two incredible talents that would undoubtedly make the Phillies a better team for 2019, they might just be better off sitting on their hands and waiting two more years for the eventual biggest free agent in Major League history – New Jersey’s own Mike Trout.

Trout, undeniably baseball’s best player, is set to hit free agency following the 2020 season. The outfielder will be 29 and more than likely ready to leave Anaheim, where the Angels have failed to build a contender around him.

So, why not return home to his childhood team in Philadelphia?

As a free agent, Trout will likely command one of the largest contracts in the history of sports. At a time when fewer and fewer teams are willing to pony up for aging free agents, the Phillies could take a risk and offer the most money to the game’s best player.

However, the only way they will be able to afford Trout is if they exercise restraint this offseason and next. That means playing the Machado and Harper markets very carefully.

Both Machado and Harper come with significant question marks. Machado came under fire during the 2018 postseason for his admitted lack of hustle, while Harper is coming off of his worst season since 2014. While their youth and talent are attractive, both remain risky free agents.

Furthermore, neither is a perfect fit for the club the Phillies currently have constructed. Adding Machado would force former top prospect Maikel Franco out of a spot, and if Machado insists on playing shortstop, would force Segura to play out of position at third. Similarly, signing Harper would cause another former top prospect, Nick Williams, to lose playing time.

These concerns don’t exist with Trout. The centerfielder would bump Odubel Herrera, who has an unclear future after a rough 2018, to the bench. McCutchen will be a free agent after Trout’s hypothetical first year in 2021, allowing a move to a corner spot if necessary.

The Phillies definitely shouldn’t just drop out on Machado and Harper and cross their fingers that they can be successful the next two years while convincing Trout to come home. But, they should certainly exercise caution.

They are currently competing with the Chicago White Sox for both players, but there are a handful of other potential suitors for Harper. The Los Angeles Dodgers and San Francisco Giants are lurking, looking to scoop Harper up on a shorter-term deal, while teams like the Atlanta Braves, St. Louis Cardinals and his former team, the Washington Nationals, make a lot of sense for the outfielder.

An attempt to add both Machado and Harper would likely cost the Phillies somewhere in the range of $60-80 million per year over the next eight years at least. This cost could prove prohibitive, especially when considering that with natural league inflation, Trout could end up costing upwards of $50 million per year.

So, perhaps the right approach for the Phillies is to drop out on Harper and keep an eye on Machado’s market, seeing if they can snatch him for a reasonable price while avoiding Harper’s bidding war. They could then flip Franco in a deal to add to their pitching staff and enter 2019 with a truly competitive club.

Adding Machado would make the Phillies downright fearsome in 2019 and 2020, and if they were to snag Trout as well, they could be baseball’s best team entering 2021. Machado would be 28 and Trout would be 29, with plenty of their best baseball still ahead of them.

The Phillies have already added pieces and could stand to add further, spending some of the money they’ve saved up over the past few difficult years. However, I would urge Middleton to be cautious, and not to spend too “stupid,” or else he could risk losing the biggest fish in the game’s history a few years down the road.