Caleb Wilfinger

Deputy Editor
Google News
Caleb is a Deputy Editor at Pickswise who resides in Upper Manhattan and has spent time in Philadelphia and Washington, D.C. He has been handicapping various sports since 2018, including NFL, NCAAF, NBA, NCAAB, MLB and tennis. The futures market is his favorite to target and he has a passion for sharing his plays with the Pickswise community.
Live Picks 9
Live Parlays 1
Weekly News Articles 8
Location
New York
Favorite Sports
Favorite Teams
Kansas Jayhawks
Los Angeles Dodgers
New York Giants
New York Knicks
Greatest Betting Win
One of my favorite sports betting memories was certainly in October of 2022, when I successfully cashed a 5-team Round Robin parlay involving games I had already played as straight bets. It involved Penn State catching 16 at home against Ohio State, along with Notre Dame, UCF, Louisville and Baylor all on the money line as underdogs. The Irish and Cardinals took care of business early by crushing their opponents and Penn State hung tough to cover the inflated number against the Buckeyes. Meanwhile UCF pulled out a thriller against Cincinnati, leaving me only a Baylor victory away from a serious 50U profit. Thankfully, the Bears made quick work of Texas Tech in the second half and I was able to watch the 4th quarter with a smile on my face. This was one of three 5-leg Round Robin parlays I cashed during the 2022 college football campaign, as part of what was a terrific season on the gridiron.
Greatest Achievements
Finished with a win rate of 63% in weekly 2022 NCAAF best bets column, highlighted by an 8-0 run to close out championship week and bowl season 25-8 (76%) YRFI/NRFI run from June through August 2023.
Education
Caleb attended Penn State University, where he covered Penn State football and basketball for 3 years (along with many other sports), getting an up close and personal look at the grind of a full collegiate athletics regular season. His two bachelor's degrees were in Journalism & Political Science, with sports journalism as a primary focus. During his senior year, Caleb began moving away from betting casually and turning into a sharper bettor, including creating systems, compiling data for multiple sports, etc.
Experience
5+ years betting experience 3+ years as a sports handicapper 10+ years as a sports journalist Caleb has been betting legally since 2019 but his history with gambling predates that, as he regularly picked NFL games against the spread throughout his college tenure. In 2021, Caleb started handicapping college football games for Pickswise and turned a profit for the season. After moving into a full-time Deputy Editor role in 2022, Caleb has had plenty of success and winners for the site’s users, most notably in college football, NFL and the MLB YRFI/NRFI market.
Favorite betting market / type
Futures and Point Spreads.
Favorite bookmakers
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Caleb's Picks

Game Totals Pick
Under 51.5(-110)

This is a game where I would’ve loved to get the over at anything in the upper 40s, but now that we’ve exceeded the key number of 51, the under is the only way I can look on Sunday. For starters, the Ravens offense should be able to move the ball in this game, just like they did against Pittsburgh and this same awful Cincinnati defense two weeks ago. However, the reason why Baltimore failed to win either of those games was largely due to the fact that it couldn’t finish drives in the red zone. This has been a common theme all season long, and it should continue into this contest. Conversely, the Bengals were handed outstanding starting field position on a number of their drives against Baltimore back on Thanksgiving, and we can’t expect that to carry over into this game. As previously mentioned, Tee Higgins’ status is uncertain, so I’d look for this game to be a bit slower paced from both sides in what should be very cold conditions in Cincinnati.

Ravens vs Bengals prediction: Under 51.5 available at time of publishing. Playable at that number.

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Game Totals Pick
Under 42.5(-110)

Regardless of which team wins this game, the under is one of my favorite totals of the week — and for good reason. As previously mentioned, both teams have really struggled with protecting the quarterback and that certainly shouldn’t change on Sunday. Los Angeles’ offense was largely inept against Philadelphia, and it took 5 turnovers from the Eagles for the Chargers to emerge victorious. Herbert should be in for another long afternoon against a Chiefs front that just played a very strong game a week ago and should be primed to put forth its most focused effort in what is a must-win game for Kansas City. On the other side, Kansas City’s offense has been up-and-down all season long, and while the Chiefs are due for some positive turnover and late down regression, the Chargers defense is still a top-10 unit across the league and should be able to keep Kansas City to 24 points or fewer. Let’s look to the under in what should be a brutally cold game in Kansas City.

Chargers vs Chiefs prediction: Under 42.5 available at time of publishing. Playable to 41.5.

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Player Receiving Yards Pick
B. Irving (TB) - Over 20.5 rec yds(-114)

Bucky Irving has dealt with a ton of injuries in his 2nd season in the NFL, and while the Buccaneers’ running back has struggled on the ground in his 6 games this season, he’s been very active in the passing game out of the backfield. Irving shouldn’t get as much of a workload on the ground given that this game is taking place on a short week and Rachaad White should split the carries in this matchup.

The Oregon product has been a consistent target for Mayfield in the passing game, with Irving racking up 23 receptions in his 6 games played this season to go along with 240 receiving yards. Irving has cleared this number in each of his last 5 games played, so let’s go back to that well on Thursday Night Football.

Point Spread Pick
TB Buccaneers -4.5(-110)

For the first leg of our Falcons vs Buccaneers Same Game Parlay, we’re going to be backing the home team laying the points. Tampa Bay has been quite poor in recent weeks, as the Bucs have dropped 4 of their last 5 games. Despite the fact that Todd Bowles’ team appears to be in the midst of a massive slide, this presents the Buccaneers with a nice bounce-back spot in a game where Tampa Bay should finally have the likes of Mike Evans and Tristan Wirfs back in the lineup.

It goes without saying that this should be the healthiest the Bucs offense has been in some time, and that should put them in position to succeed against a Falcons defense that is on the decline of late. I can only look toward the hosts on TNF.

Point Spread Pick
BAL Ravens -2.5(-110)

For all intents and purposes, the Ravens appear to be a broken team at the moment. After all, Baltimore just lost back-to-back games against AFC North foes to squander its position at the top of the division and suddenly put itself in real jeopardy of missing the postseason. Lamar Jackson is clearly playing through some kind of injury, and his supporting cast has not exactly been helpful in recent weeks, either. To make matters worse, the defense is regressing a bit after about 6 weeks of improved performance following a slow start to the season. Despite all of that, I’m actually going to hold my nose and back Baltimore as a short road favorite in Cincinnati this week in what is essentially a must-win game for John Harbaugh’s team.

A few weeks ago, Cincinnati went into Baltimore and comfortably dispatched of the Ravens in Joe Burrow’s first game back in the lineup. However, the Bengals were pretty fortunate to win that game, as Baltimore finished with a whopping 5 turnovers, including a game-changing fumble from Isaiah Likely as he was about to cross the goal line late in the first half. The Ravens were the clear better team in the box score against Pittsburgh last week, as Baltimore outgained the Steelers by more than 100 yards and controlled the time of possession, but ultimately struggled to convert in the red zone and was even stripped of a crucial touchdown by a questionable overturn from the replay booth. Just about everything that can go wrong has gone wrong for Jackson and company in recent weeks, so there should be some positive regression coming Baltimore’s way on Sunday. Additionally, Cincinnati’s defense has been a mess in the ground game and against tight ends, which spells good things for Jackson, Derrick Henry and the stable of capable Ravens tight ends. And while Joe Burrow and the Bengals just scored 34 against the Bills a week ago, it’s unclear if Tee Higgins will be in the lineup for an offense that has to score 30+ every week to put itself in position to win. I’ll back Baltimore to bounce back in this spot.

Ravens vs Bengals prediction: Baltimore Ravens -2.5 available at time of publishing. Playable at that number. 

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Point Spread Pick
KC Chiefs -4.5(-110)

One of the most important matchups of the weekend in the NFL comes in Kansas City, where the Chiefs will host the Chargers in what is now a de facto elimination game for Kansas City. A season ago, the Chiefs were basically perfect in 1-score games all season long, until they reached the Super Bowl and were embarrassed by the Eagles. Since that point, Andy Reid’s bunch has floundered in close games this season, with much of their current predicament stemming from the fact that they are just 1-6 in games decided by 1 possession. Unlike the 2024 campaign, this Chiefs team is actually due for some positive regression, and I’m of the opinion that Kansas City’s bid for another playoff berth will continue for at least a few more weeks.

Despite their rampant offensive line issues and a run game that has basically been nonexistent for most of the year, this is still an offense led by Patrick Mahomes that is surprisingly 4th in DVOA on the season. They’re also finally in a good situational spot this week against a Chargers team that is coming off the biggest win of their season and will be traveling to Kansas City on a short week. Given the fact that temperatures are expected to be well below freezing and we should see some sustained wind in this game, it’s hard to see Justin Herbert seeing much success with his broken left hand in the blistering cold. The Chargers offensive line is a revolving door at the moment, and they just allowed a whopping 72% pressure rate against the Eagles on Monday. That doesn’t bode well for a matchup against a Kansas City defensive front that is coming off a very strong game against Houston a week ago. The Chargers’ game plan is one that is going to involve a heavy dose of the run game and a ton of deep shots, and Kansas City has done very well in both of those areas of late — with the Chiefs ranking 8th against the run over the last 5 weeks. All things considered, this should be a game where Kansas City flexes its muscles en route to a victory by at least a touchdown at home.

Chargers vs Chiefs prediction:Kansas City Chiefs -4.5 available at time of publishing. Playable to -5.5.

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Game Totals Pick
Over 43.5(-125)

This is an instance where I’m bullish on a higher-scoring game than what the market is expecting. On one side, the Buccaneers offense isn’t what it was earlier in the season, but Tampa Bay has a pretty favorable matchup on Thursday against an Atlanta defense that has been trending downward in recent weeks. In fact, the Falcons have surrendered 28 points per game over the last 7 weeks, and Atlanta has allowed 30 or more points in 4 of those contests.

On the other side, the Falcons offense has shown flashes of life with Kirk Cousins back at the helm in recent weeks, and Tampa Bay’s defense (20th in EPA per pass) just struggled against Tyler Shough and the anemic Saints offense a week ago. With that in mind, let’s roll with the over on TNF.

Game Totals Pick
Over 52.0(-110)

After a long and eventful college football regular season, the most wonderful time of the year is finally here. Bowl season might not be as essential across the college football landscape as it once was, but it still presents bettors with a plethora of games to handicap and wager on. The first matchup of college football’s unofficial postseason features a couple of strong programs, as the Boise State Broncos will take on the Washington Huskies in the LA Bowl on Saturday. Both teams are expected to be mostly intact in this game, and we shouldn’t see either side impacted all that much by opt-outs and potential transfers. With that in mind, I’m going to eschew taking a side on the spread and focus on the total in this contest.

For starters, Washington has been able to work through its injuries over the last few months and the Huskies should be healthier coming off a bye week. Furthermore, it looks like Washington is motivated to play in this game, as star running back Jonah Coleman and future NFL wide receiver Denzel Boston should be in the lineup on Saturday. Head coach Jedd Fisch recently stated that he expects all of his starters to suit up in this game, outside of those with long-term injuries. With that in mind, this offense is extremely dangerous, especially with quarterback Demond Williams playing behind an offensive line should be healthy for the first time in well over a month. Washington has shown that it can score with anybody when healthy (5th in success rate, 15th in EPA per play, 17th in points per drive), and it shouldn’t face much resistance against a Boise State defense that is 117th in points per quality drive allowed and has struggled against the run all season long.

On the other side, the Broncos offense should be largely intact for this game — including quarterback Maddux Madsen and the dynamic running back trio of Dylan Riley, Sire Gaines and Malik Sherrod. Latrell Caples and Chris Marshall should be able to generate success on the outside against a Washington pass defense that has struggled when stepping up in class this season. Both of these teams don’t play at an extremely fast pace, but given that it is the final game for a lot of key contributors on both offenses, I can’t imagine either unit taking their foot off the gas in a spot where they’ll both have a favorable matchup against their opponent. With nothing troubling in the weather forecast on Saturday, this game should finish in the mid-50s. Let’s start off bowl season with plenty of points.

Boise State vs Washington prediction: Over 52 (-110) available at time of publishing. Playable to 52.5.

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Heisman Trophy Winner Pick
D. Dampier to win Heisman Trophy(+6000)

This is a shot in the dark compared to some of the favorites on the board, but it’s an educated wager on a quarterback that I could see making a major leap this fall. Devon Dampier electrified the Mountain West at New Mexico a season ago, racking up 31 total touchdowns (including a whopping 19 touchdowns on the ground) in a season that saw him take a major step forward from his freshman campaign.

Now, the 3rd-year starter steps into a promising situation with a Utah team that handed the reins over to former New Mexico offensive coordinator Jason Beck, a respected offensive mind and a surefire upgrade from what the Utes had last season. The Utes also upgraded their weapons on the perimeter via the transfer portal and get a pretty favorable schedule compared to a few other contenders in the Big 12. I’ve got Utah favored in 11 games and if the Utes are able to navigate their way through a couple of tricky conference games, they should certainly find themselves in the Big 12 title game come Championship Weekend. That alone gives this 60-1 ticket a ton of value, so Dampier is worth a sprinkle at this number.

Caleb's Parlays

Falcons vs Buccaneers TNF Same Game Parlay
Yesterday
Atlanta Falcons
Tampa Bay Buccaneers
ATL Falcons @ TB Buccaneers · Point Spread
TB Buccaneers -4.5
Our Analysis

For the first leg of our Falcons vs Buccaneers Same Game Parlay, we’re going to be backing the home team laying the points. Tampa Bay has been quite poor in recent weeks, as the Bucs have dropped 4 of their last 5 games. Despite the fact that Todd Bowles’ team appears to be in the midst of a massive slide, this presents the Buccaneers with a nice bounce-back spot in a game where Tampa Bay should finally have the likes of Mike Evans and Tristan Wirfs back in the lineup.

It goes without saying that this should be the healthiest the Bucs offense has been in some time, and that should put them in position to succeed against a Falcons defense that is on the decline of late. I can only look toward the hosts on TNF.

Atlanta Falcons
Tampa Bay Buccaneers
ATL Falcons @ TB Buccaneers · Game Totals
Over 43.5
Our Analysis

This is an instance where I’m bullish on a higher-scoring game than what the market is expecting. On one side, the Buccaneers offense isn’t what it was earlier in the season, but Tampa Bay has a pretty favorable matchup on Thursday against an Atlanta defense that has been trending downward in recent weeks. In fact, the Falcons have surrendered 28 points per game over the last 7 weeks, and Atlanta has allowed 30 or more points in 4 of those contests.

On the other side, the Falcons offense has shown flashes of life with Kirk Cousins back at the helm in recent weeks, and Tampa Bay’s defense (20th in EPA per pass) just struggled against Tyler Shough and the anemic Saints offense a week ago. With that in mind, let’s roll with the over on TNF.

Atlanta Falcons
Tampa Bay Buccaneers
ATL Falcons @ TB Buccaneers · Player Receiving Yards
B. Irving (TB) - Over 20.5 rec yds
Our Analysis

Bucky Irving has dealt with a ton of injuries in his 2nd season in the NFL, and while the Buccaneers’ running back has struggled on the ground in his 6 games this season, he’s been very active in the passing game out of the backfield. Irving shouldn’t get as much of a workload on the ground given that this game is taking place on a short week and Rachaad White should split the carries in this matchup.

The Oregon product has been a consistent target for Mayfield in the passing game, with Irving racking up 23 receptions in his 6 games played this season to go along with 240 receiving yards. Irving has cleared this number in each of his last 5 games played, so let’s go back to that well on Thursday Night Football.

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Caleb's Analysis